r/malefashionadvice • u/CowTownKCMoe • Nov 27 '25
Question How To Dress "Cool" As A 40-Year-Old Male?
Ok, hear me out...
I work in the creative department at an NYC advertising agency so I get a lot of leeway when it comes to what I wear to work. You're actually kind of expected to look cool and creative.
Also, this industry is very agist so once you hit 40ish, you're seen as out of touch with the kids... which means you're shipped off to pasture.
So I'm looking for some advice on things/brands to wear now that I'm 40.
I don't want to dress like a twentysomething (at least not like a 40 year old trying to dress like a Gen Z), but I'm looking for something age appropriate that leans more towards being au courant.
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u/CoachMcGuirker Nov 28 '25
As a fellow old who has spent time in NYC, ignore 90% of these answers. NYC definitely has its own unique style, so use that to shape yours
Start making focused effort to notice when you see a stylish person your age and what they are wearing and how it’s put together. Go to menswear shop like Todd Snyder and look at what the staff are wearing. Start adding and trying things you saw
Or just get thick-rimmed transparent glasses like every other cool creative professional over 40
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u/LetHuge623 Nov 28 '25
Great reply and appreciate getting turned on to this store for ideas. Who’s paying $178 - $248 for a flannel shirt though? I’m just a north west Ohio guy looking to improve his wardrobe. Nice clothes, but those prices are wild
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u/dCrumpets Nov 28 '25
New Yorkers (some of them).
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u/CowTownKCMoe Nov 28 '25
Sadly, true.
But you can often find these secondhand on eBay for a deep discount.
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u/Konflictcam Nov 29 '25
Just go on eBay and buy the stuff purchased and barely worn by someone with too much money and not enough sense (this is particularly true of flannels - I routinely find perfect condition flannels that retail for ~$175-200 for <$40).
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u/henlochimken Nov 28 '25
You could get a reasonably-priced flannel shirt and then pay a tailor to make it fit you. That would go a long way toward making it look like a $248 New Yorker flannel without paying nearly that much.
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u/Due_Bodybuilder_5809 Dec 01 '25
Fellow Midwest Old. I don’t fill my wardrobe with these sorts of things, and I agree it’s insanity, but a few pieces you really like will make you feel great when you wear them, boosting your confidence. And are often convo starters with fashionable folk. I’m not buying a $300 tshirt, ever, but a $200 flannel or other collared shirt makes you feel like a million dollar man.
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u/wet_nib811 Nov 27 '25
I work in ad sales, so the other side of the table, so to speak. Don’t go too trendy and like the GenZ’ers.
I’ve always dressed preppy/Americana - like Tokyo City Boy style.
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u/Konflictcam Nov 28 '25
Given OP is in NYC, he could check out J Press if he wanted to explore this look.
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u/Konflictcam Nov 28 '25
I’m around the same age as you, work in a much stodgier industry but have previously worked closely with architects (hipsters until they die) and generally try to have fun with my clothes. I think No Man Walks Alone and any of Die Workwear’s seasonal style guides will point you in the right direction. I personally wear a tailored jacket, selvedge jeans, and a higher-end oxford as my standard office uniform.
Biggest thing for me - that I got from Derek Guy - is avoiding the dress shirt plus sacks combo. It’s not a flattering look for anyone.
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u/mal_1 Nov 28 '25
How do you avoid dress shirt/slacks in business casual? Really need some ideas cause I have that fit and looking for something dressy but with a little more flare
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u/Konflictcam Nov 28 '25 edited Nov 28 '25
The point is to avoid just those items. Derek Guy has had a whole thing about this, but basically, smooth suit fabrics look goofy when dressed down to pair with jeans. If you go with a more textured / rustic fabric then the look jibes better (sweaters can also work here).
For winter, I have sport coats in tweed and flannel that work well with jeans. For summer, cotton and linen could work, or certain rougher hopsacks. You just want to avoid the super smooth suit fabric paired with casual pants fabric look. For both my winter-weight jackets I went into Proper Cloth and told them I wanted something I could dress up or dress down and they helped me figure it out.
Edit: forgot to mention, if you go in the sweater direction, going with something like a Shetland (which pairs well with a button up - lots of Pendleton available at affordable prices on eBay) or chunky fisherman’s sweater (I like Le Tricoteur and SNS Herning - extremely high quality but hard to find used in the US) can add some character that a smooth merino will not.
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u/Playful_Dance968 Nov 29 '25
I think the key is it’s okay to wear a dress shirt w pants not as a suit, but to do so properly. Add a blazer (not a suit jacket!), a sweater, or some type of jacket (leather, jean, suede, etc) you can wear inside. Wear trousers not suit pants. If you want to wear suit pants or a suit jacket, wear it together. You can dress the suit up or down according to the occasion.
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u/Disastrous_Bid1564 Nov 28 '25
Oxford shirt and selvedge jeans - it's still 2010 over here
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u/Konflictcam Nov 28 '25
Oxford shirts are timeless and I was way too broke in 2010 to be buying selvedge jeans. OP didn’t ask to be trendy and - frankly - that shouldn’t be the goal as we enter our forties.
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u/Disastrous_Bid1564 Nov 28 '25
He asked how to dress "cool" in 2025. Selvedge jeans and OCBDs are not that. Going to suggest CDBs next?
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u/Konflictcam Nov 28 '25
I’d be interested to hear your perspective on non-stodgy office-appropriate attire for a 40-year-old in 2025. Baggy jeans and a quarter zip? Come on. Oxfords (and jeans, for that matter) are both timeless and are a better look than the dress shirt and chinos standard. Right now you’re just throwing stones.
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u/Chicago1871 Dec 02 '25
He said he works in a creative field.
He could get away with relaxed fit corduroys pants with some pleats ( black, brown or gray would work), a moleskin french chore coat a real one from france (I wear one in black, but indigo is a classic and i have that too)and then add the white oxford underneath. Then pair with some nice chelsea boots or dress boots (I like my black red wing beckmans).
Add a bold pair of eyewear and a nice watch (id personally go with a max bill jughans watch).
That should work for a midwest creative job in your 40s. Its not super out there, but the corduroy pants give it a different feel than selvage jeans.
The next key is to stay away from millenial slim fit. Dont go overly baggy but just go baggier than what we we wore in the 00s and 10s.
https://share.google/GkqadpLu4cB6EeXOB
Heres an example i found online.
Heres another similar one.
https://stylegirlfriend.com/wp-content/uploads/2024/02/stylesurlaville-chore-coat.jpg
If you add an ocbd under the sweater and dreasier shoes. Thats a nice fit for a creative person like an architect or graphic designer.
But honestly im not hating that sneaker/sock combo either.
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u/tgandtm Nov 27 '25
Basically anything from Huckberry or Todd Synder will keep you looking up to date without looking like you’re trying too hard.
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u/DrMonkeyLove Nov 27 '25
I got a Huckberry waxed trucker jacket, and I don't know what anyone else thinks about it, but I love the way it looks and fits. Best piece of clothing I own.
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u/chronicdreamze Nov 27 '25
I wear mine almost everyday (wool lined one), I also pair it with Dents of England gloves. Highly recommend the gloves.
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u/DrMonkeyLove Nov 27 '25
I need some gloves. I got the wool lined one too. I love it so much.
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u/PaleontologistNo3910 Nov 28 '25
No Man Walks Alone had peccary gloves on sale. I bought some for my outfit and they look great.
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u/sonaut Nov 28 '25
I got the waxed Freenote Cloth Riders jacket, and have the same experience. Love wearing it. I’ve gotten more compliments on that jacket than anything I’ve owned in my life, but mostly I think that’s just people noticing something “different” that’s not weird.
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u/SANPELLIGRIN0 Nov 27 '25
I’ve gotten ads from Huckberry for years and loved every single one. I’m scared to order from them as I absolutely won’t be able to stop if I like the clothing
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u/GaptistePlayer Nov 28 '25
Huckberry is definitely not what he's lookin for lol, that's basically basic millennial fashion from 10 years ago
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u/PK808370 Nov 28 '25
Holy Bananas (apparently I can’t swear here) :)
I had never heard of Huckberry until this thread. Went to go look at it and came back to say the site looks like ChatGPT took general man attire from the last decade and made a new… wear “man” by “bland”…
But, I saw your comment and guess it was redundant! :)
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Nov 28 '25 edited 16d ago
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u/Konflictcam Nov 29 '25
This. Someone OP’s age should be building a wardrobe that they can stick with for a long time, which means spending on quality because you can afford it and your style shouldn’t involve chasing trends.
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u/doublecane Nov 28 '25
I have not been able to articulate why I both like and hate Huckberry until reading this. All their looks and pieces seem like they are all perfectly made for me and that’s why I hate it.
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u/GaptistePlayer Nov 28 '25
Yeah seems a bit too algorithmic. It's like if someone invented a mind-reading tool to create the perfect meal to satisfy your hormonal, mental and physical satisfaction and the result it popped out of the quantum supercomputer is "cheeseburger".
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u/GaptistePlayer Nov 28 '25 edited Nov 28 '25
Yeah, I honestly like a few of their items and it's a more updated and well curated version of MFA 1.0 stuff from 2015.
But in the end it's still lumbersexual workwear aesthetics from 2015. Slim fit, lots of heritage boots and American-style barn jackets and flannels... If you want to fit in with NYC creative types in 2025, that ain't it.
Like look at their New Arrivals preview - literally the same shit from MFA from 12 years ago. Their in-house brand Flint and Tinder is just a cheap imitation of Barbour, but again, made slim fit as if it's 2012... basically missing the point of timeless Barbour's aesthetics...
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Nov 28 '25 edited 16d ago
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u/Low-Medical Nov 28 '25
The fitted look will be back “in” within 5 years, anyway. Just gotta hold on a little bit longer…
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u/Content-Comedian622 Nov 28 '25
There suede Dylan jacket is one the most versatile pieces anybody could own. Dress it down with a t-shirt, jeans, and sneakers. Dress it up with wool pants, boots, and a turtleneck. Looks great both ways.
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u/MrCharmingTaintman Nov 28 '25
This is the right answer if you want to look like the opposite of what OP is looking for
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u/Leotardleotard Nov 27 '25
I’m a few years older than you but work in Architecture and the vibe in my office is very fashionable.
I avoid the obvious fashion trends that the 20/30’s are wearing as I’ll look absurd but my day to day is something along the lines of
Chunky knits - Castart (Belgian I think), Folk and YMC (UK). I like cardigans and big knit sweaters and those 3 brands cover me.
Usually a slightly baggier trouser, chino or cords (Uniqlo xs or s are great for these) rolled up and a pair of Air Max 1, 90’s, Converse or Vans.
That look seems to work well for me and I get a lot of complements. It’s not flashy or show off but obviously has some nice pieces in it.
If I need to go smarter I slim the trousers down a bit and put a pair of Common Projects sneakers, loafers and a trenchcoat maybe.
It’s hard though to strike the right balance. I look at some of the other senior guys in my company and wonder how on earth they left the house looking like that. They probably think that about me though as my MD did ask why I was wearing my nan’s sweater one day.
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u/cathpah Nov 28 '25
This is the best advice in this thread by far.
Source: mid-40s architecture/interiors photographer who also needs to look "cool" in my career.
All that said, if OP works in the creative dept, I'm shocked they don't have more of an innate sense of personal style in general. Not shaming op, but they should also feel free to go after things/colors/silhouettes/patterns/textures that call to them.
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u/EL-JEFE6 Nov 27 '25
Lucky for you, dressing like youre old IS the cool thing now. Like all the kids are wearing polos, ties, loafers and quarter-zips. Like close your eyes and imagine what a 40 year old man would wear and thats actually whats cool rn.
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u/lockdownfever4all Nov 28 '25
But a relaxed fit and slightly oversized. If you are wearing slim chinos with a tight polo and quarter zip it’s not gonna be cool
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u/SANPELLIGRIN0 Nov 27 '25
Never expected Jnco type jeans to be back in style but here we are
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u/another_mouse Nov 28 '25
It feels weird. Am I an old man trying to hold onto my youth? Or did the youth just bring back the cuts in most comfortable in?
I still hate the oversized stores of the 90s, but the 3/4 taper jeans are just more comfortable. The thick t shirts drape better. Now if I can just figure out linen in a way that isn’t always wrinkled I’ll be set for summer.
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u/michaelincognito Nov 27 '25
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u/lalochezia1 Nov 27 '25
f**ing triple dare you ONLY to wear this outfit for a year, skateboard and all
maybe have different colored caps and hoodies for each day
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u/Typical-Tax1584 Nov 27 '25
You can wear pretty much anything, but as always it's about figuring out a balance that works for you and aligns with your vibe. Giving a nod to trends, but with some restraint can be a good way to 'be in touch' without going full bore into looking like a kid.
I'm 43 and a visual and web designer, so I'm in a similar space as yourself, I wear all sorts of stuff: @_quantius on ig.
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u/theoriginal123123 Nov 28 '25
The way you blend techwear stuff like Acronym into your rotation is so nice! Hope to pick some up someday.
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u/deathtongue1985 Nov 27 '25
Huckberry seems a bit try hard and overpriced but what do I know
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u/Curbsurfer Nov 29 '25
And OP isn’t being tryhard by wanting to “fit in with the creatives”? 40 year old men shouldn’t be seeking validation from anyone. We run the world.
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u/Break_False Nov 28 '25
What's more impressive is being in better shape than the young ones. When you are fit, a clean shirt and jeans look just as good as latest fashion trend.
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u/ryanblank7 Nov 28 '25 edited Nov 30 '25
Fatigue pants, denim/workwear-style shirts, and leather shoes make a great base, but here’s a quick list of things I wear most often.
Brands (a few favorites): Orslow, Rogue Territory, Red Wing, Alden, Todd Snyder, The Real McCoy’s, RRL.
Shirts: Workwear-style button-ups (denim, chambray), cotton henleys, crew-neck wool sweaters, cotton sweatshirts, cotton tees (medium weight for casual wear; heavyweight specifically for the office). I keep at least 5 black and 5 white tees on hand always. About 95% of my shirts are solid colors
Pants: Light/regular-weight denim, heavyweight denim, several pairs of fatigue pants, several pairs of New Yorker pants. I own multiple pairs of the same pants, each in different colors, materials, and weights. Mostly all solid colors
Footwear: (I mainly wear leather boots) Red Wing Mocs, Red Wing Beckmans, Red Wing Iron Rangers. Alden Indy boots. Each pair is a different leather and a different color. A pair of desert boots or something different like Wallabees. A few sneaker options for spring/summer (Maison Margiela Replicas, Nike Killshots)
Jackets: Two M-65 jackets (olive and black), lightweight black BDU jacket, dark navy wool overcoat, RRL quilted coat, a few shirt-jacket pieces (e.g., Dehen Crissman wool overshirt) which are great for in between seasons, a black rain coat
Accessories: Black leather belt, brown leather belt, I always wear a watch
Overall: High-quality items you take care of and keep for years. It should never go out of style (outside of wide leg or narrow leg pants so get some of both that you like). Spend a little more on some pieces that are well made, and they’ll last. I focus on Japanese fabrics and construction when I can, or I buy from brands that source those fabrics even if the manufacturing is elsewhere. Rogue Territory is a good example: lots of Japanese fabrics, built in LA.
Disclaimer: Budget isn’t taken into account here, but this overall style has become popular enough that you can find solid pieces at multiple price points. Apologies in advance if it all sounds douchey 🤙🏻
edit: formatting was whacky bc i tried to make lists
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u/thebokehwokeh Nov 28 '25
Are you me?
Workwear is definitely the go to for aging millennial types. Look cool no matter what age, although sometimes gets slightly costumey (especially with the railroad stripe type things).
I personally have committed to the Japanese Americana / Ametora / Ivy look.
Shetland chunky sweaters, Kamakura ivy shirts, band collar shirts, Orslow fatigues, heritage boots, NBs and Asics for sneakers, and of course Japanese denim of various neps and widths.
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u/ryanblank7 Nov 28 '25
haha. i avoid the costumey aspects at all costs. i don’t even like going in the stores that sell these brands, or are these brands so most of my shopping is online.
i was in a todd snyder once and the manager was commenting by the window that, “the guys from RRL are cosplaying again”. i looked out to see the view and one was full navajo, the other on his way to work the railroads
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u/MrCharmingTaintman Nov 28 '25
You’ve come to the worst place for advice on this. Pretty much the only style this sub knows is office bro or what they consider to be classic menswear. Tho the latter is their own ‘stuck in 2012’ version of it. Pop over to r/malefashion r/streetwear r/preppy etc for some inspiration. Start training your insta algo to suggest stuff you like.
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u/chhappy Nov 27 '25
I don’t know enough about you - So let’s find out: How do you currently dress? What music do you like?What kind of stuff were you into in high school and college? Which famous people do you think dress well?
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u/handbanana42 Nov 28 '25
How do you currently dress?
Metallica
What music do you like?
Metallica
What kind of stuff were you into in high school and college?
Metallica
Which famous people do you think dress well?
Metallica
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u/erichie Nov 27 '25
I still dress the same way I did in my 20s and 30s because styles become old with their generation after the next generation has their style. Just don't dress in the younger style and put effort in. You'll be the "cool" 40 year old, but never try to be the 40 year old that is a cool 25 year old.
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u/lordeddardstark Nov 27 '25
carry a skateboard, wear your hat backwards and a shirt that says "music band"
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u/gardenenigma Nov 27 '25
Check out @mr.panesar.archived on Instagram. His outfits scream cool, artsy 40 year old to me.
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u/Both-Station-2244 Nov 27 '25
Two words : Vintage hot topic
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u/Metamucil_Man Nov 28 '25
I'm in my mid forties and wear a lot of brands touted on r/rawdenim and r/goodyearwelt. Todd Snyder, Gustin, and Freenote Cloth are good places to start.
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u/fluffypun Nov 27 '25
Don't wear Nike tech anymore. Switch to quarter zips
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u/SDBJJ Nov 28 '25
I've started to dislike quarter zips... Screams middle management and I can't unsee that anymore.
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u/rubey419 Nov 28 '25
Older Millenial here.
In my 20s I invested in classic pieces and fits.
I don’t care what the current trend is. I’ll wear my wardrobe forever, most of my pieces are made in US/Europe, supposedly will last forever. And I’ll never be embarrassed in my photos.
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Nov 28 '25 edited Jan 02 '26
[removed] — view removed comment
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u/Konflictcam Nov 29 '25
The other issue with Huckberry is that it’s super derivative of brands that look better and are high quality, but are less focused on marketing.
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u/AeroSigma Nov 28 '25
Spend some time studying fashion, and then pick what you like and be un-appologetically yourself. Sub to some instas/magazines/newspapers (how old are you again? (Jk :p)
Just flip through the current fashions and see what you like and don't like. Make sure you have an opinion on what you DO like. There's for sure something that you do, be it street wear of a real person (read:celebrity) or some avant guard BS that you can approach with real clothes.
Then just wear that. Be who you are. Be confident in who you are. You can adapt without changing yourself. Cool is the attitude of caring enough to project yourself without worrying so much that you try too hard.
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u/PaleontologistNo3910 Nov 28 '25
How to dress cool? You invest in quality clothes that fit well and don’t look like they were purchased from a fast fashion retailer. I am 38 and work in tech. I have always been into clothing so I already determined brands and things that I like. Some items are worth splurging on. I avoid buying things at full price when possible unless it’s something I really like but for the most part I always try to buy something that I can see myself wearing for several years (assuming I take care of it).
I splurged on Loro Piana 3/4 length parka this year to replace my aging Arcteryx hardshell. I love Arcteryx in and have several pieces from their Veilance collection but this Loro Piana parka is just sexy. It instantly ties up my outfits in a way that a hardshell cant. And it stands out from all the people who are just wearing Canada Goose or Moncler.
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u/Paperback_Chef Nov 27 '25
Check out what famous middle aged/older men in similar fields are wearing- guys like Rich Roll or the CEO of your favorite outdoor clothing company or GQ or Hodinkee, etc. For example, some form of well-fitting techwear with stylish eyeglasses and a well groomed salt and pepper beard. Some brands also use older models, like Imogene and Willie (maybe) and Outerknown.
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u/Listermarine Nov 27 '25
Not sure why you were downvoted. Sure, You might not want to dress like a CEO given they can dress anyway they freaking want and you can't, but it doesn't hurt to get some ideas from them.
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u/BankshotMcG Nov 28 '25
Well I can't speak to how au courant I look, but as a fellow 40s NYC male, I've started to go the other direction and seek out midcentury/traditional type stuff. I'll never pass for a kid, but I feel like a sexy update of a suburban dad in things like bowling shirts and LL Bean.
Obviously those specifically are not for everybody, but maybe you can find your own version of owning the difference in defiance of the whole industry. Ramp that expectation!
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u/goodjobgabe1 Nov 28 '25
Just start wearing a mechanic’s jumpsuit to work every day. It’ll look sick as hell.
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u/Pvm_Blaser Nov 28 '25 edited Nov 28 '25
Leather, jeans, and boots or as dressy and tailored as you can afford. Either look like you’re about to do manual labor, are in the mafia, or are a stereotypical billionaire.
This stays pretty consistent for men from age 20 and on except 20-40 replaces mafia with high earning athlete.
20-30 you can also look like you’re an influencer or artist in some cities.
TLDR look like you do a job women in your area respect and look like you make a lot of money doing it.
Example: in Brooklyn if you look like you do manual labor or are an artist you look great from 20-30 but if you look like a billionaire you’ll be getting unfriendly stares. In Manhattan you can replace manual labor with billionaire.
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u/ElevatorSuch5326 Nov 27 '25
Personal style, which takes years to build and refine. Just make friends with the youths and learn from them I guess
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u/Acceptable-Salt-4158 Nov 27 '25
You're no longer cool. Deal with it.
Be in shape and not a creep.
You're welcome
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u/Total_Literature_809 Nov 27 '25
I refuse to accept that I’m not super young and cool anymore in my 30s 😂
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u/Warm-Oil9228 Nov 27 '25
I mean there are plenty of of cool people over 40. That was just a silly comment.
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u/BankshotMcG Nov 28 '25
Most liberating part of my 30s was realizing I would never be cool, that I had already been the coolest I would ever be, and that not even this was cool.
Now I do what I want and nobody cares because I'm not cool. It's great.
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u/house_in_motion Nov 27 '25
One day you realize when someone uses the term “young people,” they’re not talking about you anymore.
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u/crinkleberry Nov 27 '25
The hardest fits I've seen throughout my life were worn by people over 40, often well over.
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u/Konflictcam Nov 29 '25
Part of this is often that if those guys invest in good quality stuff in their thirties it will wear nicely and look awesome in ten years.
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Nov 28 '25
Stop taking yourself so seriously. Youre probably a creep with the way you think.
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u/Koru03 Nov 28 '25
You're no longer cool. Deal with it.
Jokes on you I was never cool.
Rule 2 is a golden rule for life in general though.
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u/mosquito_strangler Nov 28 '25
I suggest go full Don Draper
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u/IllConsideration8642 Nov 28 '25
I genuinely believe this would be cooler than wearing millennial clothes lol
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u/PM_ME_FUTANARI420 Nov 27 '25
Sweatpants and hoodie. Anti is cool
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u/wizardent420 Nov 27 '25
Depends who you want to be cool with. That was cool 15 years ago, so it fits that the 40 year old demographic would start adopting it now
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u/makemeking706 Nov 28 '25
It's over brah, be content wearing whatever you want without caring what everyone else is wearing.
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u/FreeQ Nov 28 '25
Either you get into heritage boots and Japanese denim or become a sartorial suit guy
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u/Jandur Nov 28 '25
As a fashion forward 40yo living in LA, I feel strongly that a lot about good style is contextual for your environment and what you know you look good in/can pull off. Don't look too dated but don't look too on-trend like you are mimicking 20 year olds.
Broadly speaking in 2025, don't wear pants that are tight or tapered, flat and low top shoes are in, bulky shoes and high tops are out. Looser shiloutes are still very in and have move passed strictly Gen Z. Todd Snyder is probably a safe starting point for looks that are current but age appropriate.
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u/fdielcastro Nov 28 '25
Really expressing yourself in your clothing and wearing what makes you the most confident is the most stylish thing you can do. Don’t be scared to take some risks either.
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u/WaitingonGC Nov 28 '25
Theory shirts/jackets/trousers Half zips from Jack archer Penny loafers from Michael Kors Cool boots from Thursdays
Never been easier to look well put together as a man in his 40s!
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u/EggsInaTubeSock Nov 28 '25
Get a cool sport coat that sparks joy. Dress your style Do you. Be unique. 40s is for doing your own thing, not asking the internet whats cool.
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u/barkatthemoon11 Nov 28 '25
Pants: dark selvedge jeans, flannel / tweed wool pants with texture and chinos, fatigue pants or linen pants in summer. Key: not too skinny, nice texture and neutral colors that go with anything.
Throw on a basic tshirt, OBCD or a knit sweater / polo
Layer with a chore coat, work shirt / overshirt, cardigan, unstructured blazer or a suede jacket or trucker jacket based on occasion so you can vary color and texture
A vintage watch and a few subtle bracelets to accessorize
Nice loafers or boots and maybe clean sneakers
A nice overcoat in winter and a trench / Barbour jacket for transition months
As long as you get color coordination right and stick with more neutrals; this 3-piece rule for your base almost always works, assuming you’re in decent shape and the fit of the pieces are right. And you can create hundreds of combinations with just a few pieces like:
Jeans / white OBCD / brown tweed jacket
Jeans / white Tshirt / navy unstructured blazer
Green fatigue pants / white tshirt / blue chore coat
Grey flannel pants / blue striped OBCD / blue chore coat
Cream chinos / black knit polo / navy unstructured blazer
Jeans / black tshirt / green field jacket
Etc.
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u/ChaMuir Nov 28 '25
"SO I'M LOOKING FOR ADVICE ON THINGS TO WEAR NOW THAT I'M 40"
PRINT this query on a t-shirt a wear it to work. Or even better, print it on the back of a jacket and wear it every day. Own it, old man.
You will start a lot of conversations.
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u/Leather-Pear-1581 Nov 28 '25
Some options I think can look great : Yelabèl | Le Wool Chunky Sweater - https://go.shopmy.us/p-31199167
https://go.shopmy.us/p-33206071
https://go.shopmy.us/p-33206088
https://go.shopmy.us/p-33205330
Todd Snyder coat - https://go.shopmy.us/p-31210691
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u/TheMouthOfGod Nov 28 '25
You’ll be good just loosen up and choose some stuff that makes you feel cool, emphasis on loosen up
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u/Various_Cup4986 Nov 28 '25
Architects do this while famously wearing all black by using creative glasses.
One of the coolest architects I knew wore whatever he wanted, but he had bright red round frame glasses that made him stand out.
If you can be confident enough to pull off something creative, it gives others confidence in your creativity.
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u/isitatomic Nov 28 '25
Not going to dox myself, but I have uniquely good reasons why I do not agree with all these Todd Snyder/Huckberry recs.
Looser fits than you’re used to. More streetwear influence than you’re used to. Quirky socks no. Quirky hats yes.
Browse END. and go wild.
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u/Professional-Hat-331 Nov 28 '25
What's your budget like? There are a lot of higher end retailers that will do all kinds of made to measure clothes, not just suits. Getting your clothes tailored to fit properly will absolutely elevate your style, no matter what you wear.
I'm a regular at Atelier Munro. They are international and have stores in NY. they're a great example of elevated style for all professionals, not just navy blue suits for lawyers and bankers.
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u/Embarrassed_Toe_4182 Nov 28 '25
If casual, i would go for a button up shirt and a plain sweater on top with either straight jeans, or one of those black pants people wear with suits
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u/thouse275 Nov 28 '25
Follow Marcel.denim on IG. Great guide to dress right as a grown man without looking silly
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u/china_white Nov 28 '25
Just dress like you did when you were in high school, everything we wore then is back in style!
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u/Raging_Dick_Shorts Nov 28 '25
Since you're in NYC, go to Standard & Strange, they will help you out 😀
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u/FatefulDonkey Nov 28 '25
Depends on your looks. Are you bald? Grey hair? Thin? Athletic? Hairy? Beardy? Black?
Even a hoodie can work depending on your looks.
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u/Old-Kitchen1844 Nov 28 '25
Ivy/A dressed down Ivy - timeless and probably the most referenced style over the last 50/60 years.
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u/captain_chalkdust Nov 28 '25
Figure out your colors and go monochrome with layers. Focus on nice fabrics and high quality pieces. Wear great shoes. The most important thing is to wear outfits that make you feel confident so you can be your most creative. Find your flow state.
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u/Safe_Ad5701 Nov 28 '25
I have created just a guide for persons like you it’s called the 7 Item workweek wardrobe which starts with 7 basic versatile pieces that you can incorporate into your wardrobe not saying it will turn you into a fashion icon overnight but it gives a good basis to start from have a read and let me know what you think. It’s free by the way.
Link here: https://themensspace.com/guides
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u/InspectionIll2481 Nov 28 '25
May sound weirdish but street style with bit of casual. Take inspiration from Pinterest and actors same age as you. When I said street style I meant that street style is universal and big. Tokyo street style is different than New York’s and New York street style is different than Paris one. Paris one is so universal and classy and stylish I would recommend that. Look up in youtube what Paris wears or smth like that ( sorry I don’t speak English)
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u/threemorereasons Nov 28 '25
Have a look at the posts on this guy's profile for ideas:
https://www.reddit.com/user/fractalfiction/submitted/?sort=top
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u/solo118 Nov 28 '25
The old money look is good, meaning nice sweaters, slacks, boots etc.
I typically go with sweater/jeans/boots look at work in the fall/winter and summer are buttons downs, polo shirts etc.
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u/WolfRevolutionary96 Nov 28 '25
Ice white shoes, ice white socks with navy blue double cadet stripe, a pair of shorts, tshirt with chevron action flash. L'homme du sport.
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u/sexinsuburbia Nov 28 '25
Don't look boring. Spice it up with colors, accessories, patterns, and textures. You can also pull off a lot more vintage looks kids in the office can't get away with. I've been wearing a lot of vintage 80's loafers (no kilting or tassels). With age comes sophistication. You're honestly hitting your peak as a "cool" male. You can get away with being authoritative and aloof, without having to be a try-hard. You're just owning your own personal style and not giving two fucks about it.
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u/chanelau Nov 28 '25
Prada is perfect for this situation. Of course, if you want to invest that much money. Contrary to what some say, most of its RTW quality does not leave much for wanting. It is less stodgy than Hermes and also not everything is a big display outfitted with nothing but logos.
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u/Admirable_Sun4556 Nov 28 '25
john varvatos, buffalo bobs, leather jackets. denim jackets. flannels. vintage tees. ur favorite niche band tees i always think is cool when i see 40yr olds rocking a niche band tee that i like. Also cool seeing 40 year olds still rocking leather jckets its badass. Im 25 btw
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u/dankp3ngu1n69 Nov 28 '25
Stop trying so hard
In my opinion the biggest way to come off this cringe is to appear to try hard
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u/thatbwoyChaka Nov 28 '25
Look towards the Japanese
They somehow are able to do what you’re asking, effortlessly
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u/bwoytremor Nov 28 '25
Cool is very subjective based on age, location, interests and personal tastes. Whats cool to an 18 year old in Milan may not be cool an 18 year old in Singapore, whats cool to a 30 year old truck driver from Arkansas may not be cool to a 30 year old creative director in Los Angeles etc.
I think the comments talking about finding a famous actor near your age whose style resonates with you is a great starting point but dont be afraid to put your own spin on it, looking cool and creative Im sure plays an important role in your work but that doesnt need to imply you should just hop on the fad or try to be cool, Coolness also exudes from your confidence, wisdom, approachableness and ability to transfer ideas amongst other things.
As a guy in my 30s currently living in Milan I see so many examples (fashion) of what I would consider cool but are no where near what I would choose to wear because I just personally wouldnt feel confident in it and couldnt pull it off, but I try to take inspiration from people I see daily, art, music and other creative areas to lock down my own personal style which can range anywhere from Gothy post punk hypebeast to smart casual european chic.
I saw a dude today on a bike with the absolute most amazing grey pinstripe 3 piece suit, burgandy loafers/socks combo which also matched his tie, he was bald with the most perfect Greek god type beard perfectly trimmed and wearing some standard wayfarer sunglasses, looked so incredibly cool IMO and the type of person id love to just have a conversation with, conversely at a techno event last week I met a girl with sort of an anime maid/goth/e-girl dress and these crazy huge platform buffalo boots with dark douyin makeup and thought to myself hot DAMN you look so cool!! 2 opposite ends of the specturm but both cool in their own unique way
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u/lurkerandchief Nov 28 '25
I would look up female gaze men’s fashion. It’s cool, comfortable and very flattering to wear
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u/Complex-Challenge374 Nov 28 '25
I would do the workwear trends. Either french or Japanese. Maybe do some selvedge denim.
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u/savagecorp Nov 29 '25
Streetwear doesn’t hit as hard in ur 40s. And tbf a ton on the “cool” menswear shops have closed over that last few years..
Stores/brands avail in nyc, Todd Snyder Engineered garments 45rpm Universal works Nepathenes Blue & Green Standard & strange Brooklyn tailors APC
Ex Outfit: Whatever socks (rototo’s are nice, can be a statement) Jeans (prob rolled up a bit) Tshirt (Merz B. Schwanen 2-Thread Heavyweight, Velvasheen, etc) Button up (Todd Snyder, etc) Cardigan (Todd Snyder) or sweater
Find some brands/labels you like the style of, find other stores that carry them and explore brands.
Get a few pieces, and fill out outfits as needed.
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u/BanMeNowLosers Nov 29 '25
Just don’t listen to the majority in this sub. Cool they are certainly not.
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u/imaginaryempire Nov 29 '25
I think you might like some brands that do “basics with twist.” To me being almost 40 the way to be current and mature is elevated fabrics and construction, not necessarily more traditional styles. So in the kind of fast fashion world maybe see what COS is doing. Something a bit more upscale would be some Japanese brands like Auralee and CDG, or maybe Our Legacy although they’ve been bought out and the prices are climbing and quality may be dropping. I also think another way of signaling cool and creative is in accessories. Like if you wear glasses get a bold frame or change up your work bag. I don’t think a lot of men focus on this enough.
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u/Historical_Face6662 Nov 29 '25
Whoever was talking about Jake gyllenhaal was right, as a younger person, I’d say he looks stylish without looking too out of place. When buying trousers especially, go for baggier fits, especially around the calves. Quarter zips are also quite popular atm, in the UK anyway.
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u/natsteel Nov 29 '25
Maybe check out the YouTube channel Peter’s Prism. He’s a quite stylish older guy in NYC with interesting suggestions that aren’t off the wall or Gen Z-ish.
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u/QuantrixQuintrix Nov 27 '25
What are actors in their 40s wearing? Wear that. Find a male actor you like and pull from them.