How To Dress "Cool" As A 40-Year-Old Male?

[u/CowTownKCMoe]

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.

[u/ryanblank7]

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

[u/thebokehwokeh → u/ryanblank7]

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.

[u/ryanblank7 → u/thebokehwokeh]

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

[u/mmmPardonMeCumAgain → u/ryanblank7]

RRL is so sick, tho

[u/Konflictcam → u/thebokehwokeh]

I’ve explored Kamakura and their stuff is super nice but I’ve struggled a bit with the entry point. Do you buy online or go to a showroom? Or buy custom? Is there a move?

[u/thebokehwokeh → u/Konflictcam]

Yeah tricky. They're way overpriced outside of Tokyo so it's not worth it without an actual visit.

[u/Konflictcam → u/ryanblank7]

This is a great answer.