Updating my style in my mid-30s
May 20, 2022 2:05 PM   Subscribe

I'm a mid-30s guy who wants to feel more stylish (not necessarily fashionable) but without breaking the bank or radically changing my overall style.

I'm average height, I have shapely legs, short and not muscular arms, and a husky midsection I've always been very self-conscious about (but have recently decided to love my body the way it is and accept that it won't significantly change in the near future). I also hate shopping for clothes and picking out outfits so I pretty much wear the same thing every day, regardless of season: a button down shirt with the sleeves rolled up (gingham/check and tucked in when going to work, flannel/corduroy and untucked in a more casual context; sometimes I wear tshirts in summer but I get really worried about my gut being too prominent), belted black, gray, or navy jeans, and dark brown Clarks. Photos:


I'm alright with this but I want to feel cooler, more stylish, and more confident in my clothes. Sometimes I worry I'm starting to veer toward the classic dad look which I don't like. Plus I used to buy almost everything at Uniqlo but in recent years I've really struggled to find anything I like there.

What I'm looking for:
1. Ideas for items of clothing, outerwear, or footwear that build on this basic framework but push it in a more attractive or creative direction.
2. Stores, brands, websites to look out for and tips for shopping there (I absolutely hate shopping for clothes and returning clothes that end up not fitting). Made to measure is great as long as we're not talking hundreds of dollars for a shirt.
3. Other adjustments to my look that may not currently be obvious to me. Please be nice.

1. I have a lot of trouble finding fashion inspiration because people I see on the street or in pictures who have the kind of style I'm looking for are almost always way skinnier than me and look way better. People whose style I like who aren't skinnier tend to dress more conservatively than I prefer.
2. Off the rack shirts are extremely hit or miss for me: larges are almost always too large, mediums are either just right or too tight. My neck is quite thick and my arms are too short to make this a reliable process. Also slim fit and the like never fit me so my shirts are always pretty boxy looking.
3. I've started buying most of my shirts made to measure through Indochino, but even there it's bizarrely hit or miss: if I order 5 shirts with the same set of measurements, I tend to look and feel good in one or two of them, mediocre in another two, and slightly uncomfortable in the last one. Also I want more casual shirts and their casual options are generally terrible.
4. I'm open to developing a more seasonal wardrobe but it's been so hard to assemble a satisfying week-to-week wardrobe that doing four versions of it seems almost intolerably difficult. But I'm open to being persuaded.
posted by derrinyet to Clothing, Beauty, & Fashion (10 answers total) 11 users marked this as a favorite
I've always found the dappered blog to be a decent starting point. I linked the style scenarios page, which gives a good view of their philosophy. For one item of clothing I'd go with the banana republic traveler pant. They make a bunch of sub-variants so I'd try them on first, but they are comfortable and can work with a bunch of different outfits.
posted by true at 2:21 PM on May 20, 2022

I think you're in a pretty good starting place, in that it sounds like your wardrobe is full of pretty neutral pieces that will work well with a lot of things. Some low-hanging fruit in making you look and feel more stylish might be to start adding in shirts that have more color and/or texture, as everything you've described is those neutral pieces. Some colorful linen button downs in the summer, flannels and chamois for the winter, and things like chambray year round. Colorful prints on shirts will also go a long way here if you're into that. Gustin is a company I get a lot of shirts from because I care a lot about fabric and texture in my clothing (my mother owned a fabric/fiber store, thanks mom) and they have shirts in multiple fits. I've found their pants to be somewhat hit or miss in that the standard fit is often perfect but sometimes too skinny, but their shirts have been pretty reliable for me. Taylor Stitch is another company whose shirts I like. I'm sure there are plenty of other places at various price points with good stuff, those are just two I like.

I've also gotten plenty of good vintage shirts on eBay if you're willing to put in a little time sifting through all the various options there and have an idea of what you're looking for. eBay isn't a great option if you don't have anything specific in mind, but if you know you want a good mustard yellow sweatshirt, say, or a green flannel shirt, you can get really nice things at great prices.

A lot of men are scared to wear anything too colorful or interesting, but one colorful piece of clothing worn with other pretty neutral items is a great way to be more stylish and interesting. The other piece of all of this is that you always look better when your clothing fits your body well, but it sounds like you're already on top of this.
posted by lhputtgrass at 2:58 PM on May 20, 2022 [3 favorites]

I will always recommend to hire a stylist because that is exactly their job - look at your current pieces, weed out the not-quite-right ones, and help you fill-in-the-blanks. I mean if you like doing your own research on brands and developing a "look" then by all means... but if you just want someone to do all that heavy lifting for you so that you come out more stylish after a 3-hour shopping trip and you're set for the entire season? Stylist all the way!

Especially since you say you hate shopping for clothes, I'm telling you, working with a stylist will be the best, most efficient shopping experience you'll have. No more indecision about whether something works for you or not. Some instances my brain hasn't even processed how I feel about something I just put on, and the stylist will have already said, "Nope!" because they're seeing something that I'm not, and they're already handing me the next thing to try.
posted by tinydancer at 4:23 PM on May 20, 2022 [1 favorite]

First, I think you look great, and you have a great frame on which to hang clothing. Sometimes, it isn't even the basic clothes that need to change- adding in superfunky glasses or shoes (like this or this) can really up the stylishness without needing to address every single item of clothing. And doing it all at once can be too much. Also - seconding the idea of a stylist. It can often be cheaper than getting all new things, since they are working with what you already have, adding just a bit, and showing you how to make it work together.
posted by sonofsnark at 4:44 PM on May 20, 2022 [1 favorite]

I think you're starting from a good place: your clothing looks casual but polished, looks like good quality, looks like you have taste, looks like you are dressing yourself with care according to what you want to wear. Here are my suggestions for what you already have from your photos:

* I think your belt is too long. (apparently you measure your belt size by adding 2 inches to the waist size of your pants, I'm not sure if that's exactly right for everyone.)
* I think your jeans could fit better. I think the inseam is slightly too long - as a result you get bagginess around the knees - and/or they are too tapered at the ankle. I think this skinny ankle thing is fashionable but with your frame, it looks ill-fitting. Can you try a jean with a bit more of a straight leg (maybe a slim fit or relaxed fit rather than skinny)? I think it will even you out a little.
* Consider the next time you do a made to measure shirt maybe adding a half inch or an inch to the length.

For fashion inspo, maybe follow creative adult men on instagram that are not "fashion"? (My first thoughts were Josh Homme and Dave Grohl.) Maybe look for fashion inspo men in their 40s or 50s - they won't be 30 year olds trying to look 20.

For additions: I think you should get some good chinos. I know these are like the exact dad look but I think if you don't wear it with a polo shirt (or do, but a good one), or have them be ill fitting, you'll be good. You could go for gray or greenish instead of khaki, but a good khaki might be a nice change for summer. I also think you should try some slightly less neutral shirts of the same style you already like. Maybe just go for slightly more contrast with your clothes. Not crazy.

Also, shoes. I like the ones you have in the pics for an everyday look but you can mix it up with some canvas shoes (think Vans, could be black), and some everyday dress shoes that look smart (can still be worn with jeans.)
posted by vunder at 5:32 PM on May 20, 2022 [2 favorites]

Best answer: Looking at those photos, I, a clotheshorse, recommend:

Similar jeans with a looser fit, a slightly higher rise and a more robust denim. Looser, more robust jeans will look more contemporary and I feel like those hit you a little low.

Get a smaller belt in that same good brown leather. Additionally, get a couple of special belts - suede or a color or braided cord or tooled belts. You can poke around on eBay for interesting belts - it takes a little looking, but for instance I needed to replace my old standby and got a high-quality black belt with a pattern of punched lines that gives it texture and a nice italian suede.

Get chunkier shoes. From the side those have a very small profile and I think that a heavier sole and slightly bolder toe would balance your silhouette better. I think workboots are a bit played out right now so unless you really personally like, eg, Red Wing boots for their own sake, a bigger chukka boot or chelsea boots or chunky sneakers would be more my thing. As an old, I don't really keep up with sneakers - I just wear Vans slip-ons since it's easy to add color or texture with different ones.

Go slightly bolder with the pattern - a bigger check, some medium to wide stripes. Basically, a pattern that reads as a pattern from from a distance.

I like how the colors in your outfit all tone well together - the jeans are grey-black, the check reads as grey, the brown is warm. The wear on the belt looks good, too - I have no idea how fancy a belt that is, but it was a good choice. I like that you have a collar in proportion to the shirt instead of a really itty one.

If I were going to tweak that outfit, I'd go with something more like these Madewell relaxed taper jeans or these straight Gap jeans - move away from jeans that hug your calves. I also get pants from ASOS, usually the house brand cotton ones which are unexpectedly good for the money and sometimes have some on-trend features. Their shirts are bad even though enticing in pattern.

Good modern shirts are hard to find, IMO. I've talked myself into a couple of expensive shirt purchases that were just wrinkly and cheap feeling and didn't give me room to move my shoulders, so I get mostly vintage 90s shirts from eBay. Weirdly, looking for the occasional good color or pattern at various stodgy places works too - Land's End, Brooks Brothers. I like a classic fit.

Die, Workwear is an older blog and in one of those "live long enough to become the villain" twists now posts frequently about workwear. I read it for ideas and look at all the fancy brands they recommend even though I basically would never spend that kind of money even if I could - I'm too hard on my clothes. I look at GQ and Esquire - GQ's "five fits with..." feature is not at all my thing style-wise but it gives me ideas for colors and shapes.

You look like a guy who could do a little jewelry, maybe a heavy sterling bracelet or a couple of sterling rings, big but not exaggerated. I bet a couple of simple sterling rings with presence would really do a lot for an otherwise simple outfit, actually - I'm not thinking big rings set with chunky stones (unless that sounds interesting to you), just a couple of wide textured rings that contrast pleasantly with each other.
posted by Frowner at 5:45 PM on May 20, 2022 [4 favorites]

You aren't going to get what you want without putting some work in. Being stylish, even just moderately so, is work. You have to shop, and try things on, and learn designers you like, and spend some time regularly thinking about what you wear. You can maybe hire a stylist to shortcut this but it can be hard to find a good stylist, and it's unlikely they are going to do what you want in a cost-effective way.

However, you're a man, so you can do this much more easily than most women can. You need jeans that match the current styles (although honestly I think the ones you showed us in these photos are fine, but I'm not a man and don't follow men's fashion that much). You need some slacks as well, to mix things up, and possibly shorts if you live in a hot climate. You need shoes that match current styles (these shoes are not it, at all). You need a few belts that fit (not the one you showed us, which is too long). You need a collection of shirts that fit, are seasonally appropriate. The shirts, and possibly accessories, are where the more personal style elements will come in. Fun sneakers, or a jacket, or a bright shirt, or a subtle piece of jewelry, all of these tweaks can elevate and personalize your style. For shirts especially, colors/patterns, cuts, and fabrics, all of these can as I think you know totally change a look. Most stylish people either are not afraid to be bold, or have an exceptional eye for fabric and cut/fit, or both.

You can probably become more stylish by going to a big department store (or a few Uniqlo/etc type single brand stores, but realize you'll have to go more places if you do it this way) twice a year, trying things on, and refreshing some of your wardrobe basics and key pieces. To me, this is absolutely nothing in terms of effort for being stylish. Your shape seems completely able to be satisfied off-the-rack, you just have to actually try things on to figure out what will fit. Especially for things like jackets and shoes, you can really add to your style by finding nice or interesting versions that just make you look a bit more pulled together.

Once you get in the hang of this, you can find designers and styles you like that you know tend to fit you, and do more of the "shopping" online. But there's no substitute for getting into the habit of trying things on regularly and seeing what works, what you enjoy, and what feels right for you.
posted by ch1x0r at 8:07 PM on May 20, 2022 [2 favorites]

As a slightly older guy with a slightly huskier midsection, I don’t think you look bad. I agree that more substantial jeans might help, and maybe like a pair of Doc Martens, but really there are two things that stick out to me that would be easy improvements. First, you look a little rumpled. I personally don’t see this as a problem, but if you want to level up, spend more time ironing, and maybe even get your shirts pressed. Second, your color palette is pretty muted. Lots of dark, cool colors. Khakis have the possibility of contributing to the dad look, but if you get a casual pair (maybe Banana Republic?), they could add some contrast on the bottom. Then just get some brighter tops to mix in as well.

Finally, allow me to suggest that, when you’re already 80% of the way there, the next step is usually accessories. A nice watch, a colorful (or white) belt, and some fun socks would give you more bang for the buck than just buying more expensive shirts.

But yeah, you don’t look bad. You’d be one of the better dressed guys at most places I’ve worked.
posted by kevinbelt at 8:24 AM on May 21, 2022

Indochino is notoriously inconsistent. I recommend Proper Cloth for shirts.
posted by ludwig_van at 11:34 AM on May 21, 2022

Agree that your basic framework is great. One thing I'm obsessed with atm is how pants meet footwear. It's one of those small things that makes a big difference in how "put together" someone looks overall. If you see a well-dressed man in the street or in a photo, look at his ankles! How has he managed the transition between shoes and pants? Do his pants extend over his shoes, or are they tailored/has he cuffed them above? Can you see his socks? Is not wearing socks part of the outfit (e.g. boat shoes)? And see if you can experiment with some of these using stuff you already own.
posted by happyfrog at 4:24 PM on May 21, 2022 [1 favorite]

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