best dressed middle-aged lug of 2020

December 17, 2019 1:24 PM

I think I'm not dressing in a way that looks good on a not that skinny short guy in his mid 40s. I'm looking for some ideas/pointers.

15 years ago I said to a friend "I feel like I'm not dressing to my best advantage but am not sure what I should be doing." He got a slightly maniacal glint in his eye and said "I have been HOPING you would ask." He then got me to stop wearing stuff that was too large/baggy, and a couple of other tips. It was all good advice.

I was skinny then, probably 140# at 5'5". The 5'5" has remained constant, as it generally does, but my metabolism quit. I'm sure I weigh in closer to 175# at this point. I generally wear 31"-32" waist jeans at present, which seems not the chunkiest but I have a peasanty build and am, within the context of being a short guy, long-waisted, which is to say my inseam is super short.

So basically I'm a bear (or, more insultingly: a pocket cub! There is a name for everything!) with a short beard and all that. I don't think the way I'm dressing is quite what goes with that. I mostly wear jeans with a buttoned shirt, untucked. Sometimes sweaters.

I’m in my mid 40s and don’t want to look like a guy I used to work for who was my age but seemed to be trying to look like a 25-year-old twink, too-tight shirts and poofy producty hair. I think the look I am looking for might be more, well, markedly masculine than my current one, though personally I’m pretty neutral on that spectrum.

Here is a super unflattering half selfie. Fluorescent lighting, cubicle in the background, throwback slightly ill-fitted sweater, the whole nine yards. I think it makes me look even squatter than IRL, but that's fine. Send me guidance! Pretty please!

posted by less of course to Clothing, Beauty, & Fashion (16 answers total)

I think your selfie is nice, and the sweater is a nice color! To build on your existing style but step it up a notch and make it a bit snazzier, I would suggest layers. With that same outfit, you could wear a collared shirt or flannel underneath. If you don't have brown "fashion boots," they go with everything and are fashion forward but not ostentatious. I would suggest tucking in button shirts and wearing a belt (unless it's a flannel).
posted by Pfardentrott at 1:33 PM on December 17, 2019 [3 favorites]

Yes I think you're doing fine. Jeans are great at any age, which means they pretty much always look "age appropriate" and not like someone is trying too hard. The only thing I'd suggest is that button down shirts (if left untucked) tend to be slimming, so maybe a flannel as suggested by pfardentrott above, or a cotton button down shirt.
posted by WalkerWestridge at 1:47 PM on December 17, 2019

Best answer: Can you afford some months of Stitchfix? It's not bargain shopping, but six months or so of buying most/all of the pieces they sent him really helped my husband level up his wardrobe in a way that was fashionable but not too formal (he works in an indoor industry where shorts and t-shirts aren't out of place but also he's 40 and a lot of them are a good bit younger). In particular, his shopper really dialed in the right shirt and pant cuts for his body type so that stuff looks like it fits on him, which really does make a huge difference. She did a great job of adding a lot of versatile color to his wardrobe (a specific request). From there he was better able to shop for himself, plus those six months stocked him up pretty well.

I would say the number one thing is clothes that fit, including jeans. You may need to get a tailor to help with length, but go for a more-fitted slimmer cut in the hips and legs.
posted by Lyn Never at 1:51 PM on December 17, 2019 [5 favorites]

Best answer: Celebrities pay stylists for this exact service- to make flattering clothing choices for them. So just follow some celebs with your approximate build and even colouring - perhaps Jonah Hill, Seth Rogan, Zack Galiafinakis, or Jordan Peele, etc. Google image search their names plus words that will bring up candid street photos of them, like + airport, LAX, street, jeans, leather, comfortable, streetstyle, streetwear, casual, stroll, wife, baby, etc. Screengrab whatever outfits you like and use that for shopping inspiration.
posted by nouvelle-personne at 2:08 PM on December 17, 2019 [8 favorites]

The cut of your pants is still too baggy. A slimmer cut, with alterations if needed, will make you look far more updated. Don't go for any distressing on jeans - just a solid, darker color that will wear naturally. Also, wearing a layered look on top with a final layer that's either a zip up or a less structured blazer will flatter and balance. More trendy shoes and glasses frames (if you wear glasses) will go far toward elevating your look without getting out of the casual realm that you're in.

Joining something like Stitchfix or working with a stylist at Nordstrom if you like brick and mortar will help you get better choices without a lot of extra frustration and you can return what you don't like.
posted by quince at 2:09 PM on December 17, 2019 [12 favorites]

Seconding the Stitchfix suggestion, or Trunk Club, which is Nordstrom's version (I vastly prefer Trunk Club over Stitchfix, but I'm a woman so YMMV) - either will make it easy for you to try a few things and see how they work on your body.

I'd also highly recommend watching some episodes of Queer Eye on Netflix. You can fast forward to Tan's fashion sections if you want (though I find the shows really happy-making, so feel free to give them a shot!). He always explains his fashion choices so that you can learn what might work for you. He tends to repeat himself, so that will make it even easier for you to get some advice.

Good luck! You can totally do this.
posted by widdershins at 2:25 PM on December 17, 2019 [1 favorite]

Response by poster: Thanks folks. I'll see how much Stitchfix/Truck Club cost and think on it. And it sounds fun googling Seth Rogan et al.

(I enjoy Queer Eye but sometimes hate the looks Tan puts on schlubby guys, and actually tweeted at him once to stop telling guys "this makes you look short." I will always look short. So will he for that matter!)
posted by less of course at 2:29 PM on December 17, 2019 [5 favorites]

I had me a midlife crisis and I decided I am going to try to dress how I feel inside.

I started looking for inspiration on Pinterest, searching for things like "fashion women over 40" and "french fashion older women" or "edgy fashion after 40...". etc Then I made a private pinterest board & pinned anything that I liked the look of. Eventually some patterns appeared and I was able to start shopping for specific outfits.

Another big step was to really purge old clothes that I wore merely out of habit or apathy. This was a huge catalyst for releasing myself to buy new & novel things.

Also... and this was hard... I decided I would try not to overthink if I'm looking like a try-hard has-been. I still fight it. But I think feeling confident & snazzy is worth the risk.

Good luck sir!
posted by i_mean_come_on_now at 2:35 PM on December 17, 2019 [4 favorites]

Seconding the recommendation for layering! You want something that gives your outfit a bit of structure. Subtle patterns also help to make it look like you're Making An Effort.

Along with Seth Rogen I would recommend taking a look at some of the stuff Jordan Peele wears. This jacket:

https://images.app.goo.gl/1hkwvtb8oTsRMTHBA

And this jacket:

https://images.app.goo.gl/7hqrQNEn58f8GLnk8

Are both pretty good basics that will make you look put-together without having to dress up.
posted by storytam at 2:42 PM on December 17, 2019 [1 favorite]

If youre willing to go the Stichfix route you could also consider Bombfell (terrible name) - i hate shopping and got some okay stuff from them.
posted by Exceptional_Hubris at 2:44 PM on December 17, 2019

Best answer: Oh, wait, also! For very casual looks try David Chang on Ugly Delicious. A lot of the time he's literally just wearing a plaid button down shirt and jeans, but with a pattern and cut that works for him.
posted by storytam at 2:52 PM on December 17, 2019

Slimmer cut of jeans (as slim as you can go without wearing skinny jeans unless that is your preference) + nice belt.
Nice boots.
Tuck in the shirt.
Layer something, anything, under that sweater (or any shirt you wear). Button-down preferable but a crisp white undershirt just visible from the V-neck would also add polish without bulk.
Collared sweaters or jackets.
posted by anderjen at 2:57 PM on December 17, 2019 [2 favorites]

Agreed on less baggy jeans

You could try the look Nick Offerman has here and here. Jeans that fit, dark T-shirt, collared flannel.
posted by slidell at 3:02 PM on December 17, 2019

When people say "a good belt" it can be unclear what that means. So, go to the website for Narragansett Leathers and follow their instructions for ordering a well fitted belt from them. I would suggest a brown one and a black one, but I just own two identical black ones because someone lost mine and then returned it to me months later, after I had replaced it. If you don't wear any brown and don't want to, then don't order a brown belt. My buckles are nickel, but get what you like.

The simple buckles and good quality leather, plus the right fit really pull an outfit together.

As for choosing shirts that fit, if you have a Nordstrom near you, they can help you find some cuts and brands that are a good match for your build. They also alter pant hems in most (all?) their locations.

Shoes are another place that really makes an outfit come to life. Beat up athletic sneakers would make the outfit in your selfie look terrible, but a leather sneaker or oxford might make it classy and smart. Much slimmer jeans and a slightly slimmer sweater and maybe monk strap shoes would be your style. I wouldn't recommend you go for a really long pointy toe shoe, but get what you like. Keep them clean and well soled. And when you dry your sweaters, lay them flat and smooth them out to dry, instead of running them through the dryer.
posted by bilabial at 4:24 PM on December 17, 2019 [2 favorites]

My husband looks a bit like you and I feel like Trendy Butler leveled up his style a lot. Significantly cheaper than the other subs, too.
posted by shadygrove at 8:33 PM on December 17, 2019 [1 favorite]

Can I recommend some bright colours?
Here's the thing. Men dress down. the choice is always towards the darker or neutral colours.
A lot of blacks, greys, beiges and khakis.
But because of that you can get a lot of mileage in wearing something that you would normally ask "Can I pull this off?" Yes. You. Can!

My wardrobe standard was for some time a combination of black jeans and a dark green t-shirt.
I have recently bought*
a) 7 T-shirts each a different colour of the rainbow
b) a yellow Aloha shirt with flamingoes on.

I have worn various combinations of these whilst out and have got many many genuine compliments from strangers. In London!


*(I also have worn some variant on a hot pink watch for many years, it was often the ONLY colourful I was wearing)
posted by Just this guy, y'know at 4:10 AM on December 18, 2019