Help me dress more stylishly
March 24, 2016 3:51 PM   Subscribe

I'm sick of wearing boring clothes. Please point me into a new direction.

For the majority of my life I never put much importance in the way I dress. This has changed recently as I've realized, as I've realized at points in the past (albeit before it was always semi-subconsciously), that whenever I wear nice clothes I feel better and, perhaps this is just in my head, but, people seem to treat me better. And sometimes I even receive compliments, something that's always nice.

Now while I'm not 100% brand loyal, I have go-tos when it comes to accessories such as watches (Seiko / Orient), belts (Orion Leather Company), glasses (Ray Ban), boots (Timberland) and shoes (Converse) and feel that all of the aforementioned brands consistently make great, stylish products that appeal to me . . . but I'm clueless when it comes to clothes and though I have in the past owned some really great clothes, I've yet to come across a clothing brand that consistently makes great clothes. What clothing brands should I be looking for? And where should I be looking for them?

My two requirements are that the clothes mustn't be too formal and shouldn't be too pricey: right now I just can't afford to spend more than $100 on any single article of clothing. And in case it matters: I'm male, in my late twenties, am about six feet tall, have a medium-sized frame and am at the moment slightly overweight (which shouldn't be a long-term thing . . . my weight fluctuates a lot).

Thanks!
posted by GlassHeart to Clothing, Beauty, & Fashion (8 answers total) 12 users marked this as a favorite
 
Woman here but I'll share my strategy with you. To get started, I'd pick a brick and mortar store with a look you like, with affordable clothes on offer, set a budget, and start by shopping there, with the assistance of a well dressed and helpful sales clerk. Try on everything, in combinations you think you'll be wearing. Stick with the colors that look best on you. The advantage of shopping at one store to begin with is that stores sell complementary items and sizing tends to be consistent. Start with basics, not accessories. And your price point suggests you will do best if you find what you want, then await sales. When you have a sense of your own style, I'd start looking at other stores for more acquisitions.

Also, don't do trends. You maximize value and elegance and style with classic, complementary pieces that are cut well and made from good fabrics.
posted by bearwife at 4:10 PM on March 24, 2016 [2 favorites]


I remember getting a new job a while back that involved meeting more senior people more regularly and I thought I needed to up my game in terms of clothing and presentation - here's a few of the things that I think helped me dress in a way that made me feel more confident and stylish:

* Don't just think in terms of brands when you're shopping. Finding a good, small store that curates its stock with a consistent look is even better than zeroing in a specific brand. I tend to find one brand might be great for jackets, but less so for shirts - finding a good store gets round this issue because they'll be going for an overall aesthetic.

* Try and think less about finding a great jacket or shirt in isolation, and think about the whole outfit. Sounds obvious, but while you might buy clothes individually, you're always wearing them with a whole heap of other stuff so you need to be thinking about how everything fits together. The guy who writes Die Workwear does a really good job of explaining the way items of clothing work together. Or you can look at the way clothing sites like Mr Porter model items of clothing - they'll show a jacket with a bunch of other suitable items. They're doing it to encourage multiple purchases, but it's a great way of seeing how items can be matched together.

* A good way to think about whole outfits is to think about items you own already that you like and feel good in, and that you wear together regularly - what is it about it that works? The colours, the fit, the material? You can also think about people who you think look cool - from bands or movies, or magazines, or just that you see in real life - what is it about the way they are that works?

* Think about fit; spend time trying things on and try some sizes you wouldn't ordinarily - I'd never tried a size Small shirt at J.Crew because I always thought "well, I wear medium", and I was surprised by how much better it looked. For some brands, there isn't a huge difference between sizes (meaning one person can wear a wide range) and yet there will be big differences in look and feel.

* Sometimes it is worth spending the money on good stuff. You can offset this by buying stuff that's going to last - I've got some Red Wing boots that cost $200-300 but I've owned them 5 years, had them resoled etc, worn them day in day out and they look great. You can also save stuff on shopping sites and wait for the sales, or look at discount sites like Yoox, or scour eBay - Put This On does good roundups. With better quality stuff, especially if it's name brand, you will also be able to sell it on eBay, so you can try things and move them on if they don't work and not lose too much money.

Hope the above helps. The difficulty with wanting to be more stylish is that, really, it's a bit of a confidence game. And no-one can just say "hey, be more confident!" and do it. It comes over time, bit by bit.
posted by Sifter at 4:19 PM on March 24, 2016 [3 favorites]


Your personal style will probably evolve with your life. It's hard for other people to know what to tell you apart from specifics like X makes well cut shirts or Y have crappy zippers.

If I were you, I'd look at lots of clothes first and try to identify patterns of things you like. Pay more attention to store displays, magazine spreads and even online shops. Asos will give you millions of pictures of outfits. Find some instagramers to follow. Once you know your look, you can work out which brands. staples should come from trusted sources. This season's gimmicky fun thing can come from Asos.

In terms of "great", I'm not sure whether you mean well made or they look great or they're iconic or whatever. But if it's about being well made or longevity, my tip is never buy acrylic knit wear. One wash and it's bobble city. And don't buy cheap jeans. Other things you'll work out along the way in your fashion & dressing journey, like I also don't buy things I can't machine wash or need ironing.

Have fun!
posted by stellathon at 4:31 PM on March 24, 2016


also, look at people. people from within your culture. not just to see who looks good, and what you can copy, but also to see what you can steal and combine. think about the clothes you see. what makes a shirt that one person is wearing different from another (hint: it's not fucking thread count)? look at people's shapes. how does that affect what they wear? their ages. where they live. how do people combine clothes? what combinations don't you see? why?

look at people. choose who you want to be within them. then work out what clothes that person would wear.
posted by andrewcooke at 4:50 PM on March 24, 2016 [2 favorites]


I'm on the same tip these days, and here's what I've found useful:

/r/malefashionadvice
/r/malehairadvice
Primer's Style Section
Basenotes.net (for my growing cologne collection)

The rest I could take or leave.
posted by roll away the dew at 4:55 PM on March 24, 2016 [1 favorite]


I second roll away the dew's recommendations. You may be a _bit_ older than those subreddit's target demographics, but I'm sure you could still cull useful advice from them -- if not all.

/r/malefashionadvice was an eye opener for me ~5 years ago when I started putting more thought into how I dressed (I, too, am in my late 20s now). They even have seasonal posts and recommendations for the essentials and mix-and-matchers to save funds.
posted by TimBridge at 8:04 PM on March 24, 2016


This might be more than what you are asking, but I personally got a lot out of getting my colors done.

Once I was aware of what colors are more flattering on me (and then realized that pretty much my entire wardrobe was built on colors that were decidedly not flattering on me, but the clothes were trendy! and "stylish"!), I was able to shop more effectively, and I generally feel pretty good in just about everything in my closet now.

Very basically, I learned what colors tend to make my skin look washed out, and what colors highlight my eyes. That's a good place to start.

And then, yes, I agree with picking a store or two that you like and trying on everything to get a sense of how you feel in their stuff. Another good thing to try is spend some time looking at a store's website to see how they style the looks. So you're not just looking at a shirt online, you're looking at how they put the whole outfit together on the model, including shoes and usually a second layer or accessories. I find that in styling most stores tend to mix colors or patterns a little more than I would be comfortable wearing, but seeing how a jacket looks with a teeshirt vs. a buttondown or with a sweater underneath can give you ideas about whether it will work for you.
posted by vignettist at 8:41 AM on March 25, 2016


I feel like I pimp this site so much here that they should pay me, but Dappered.com is exactly what you're looking for.

Dappered, if you're interested in any sort of Internet corruption paid advertising nonsense spam thing, I'm your guy! ;-)
posted by cnc at 10:28 AM on March 25, 2016


« Older Tips on teaching semaphore?   |   Drip... drip... drip drip... drip. Newer »
This thread is closed to new comments.