Help me make this the year where I finally find some style!
December 26, 2010 7:06 PM   Subscribe

Help me make this the year where I finally find some style!

I'm a guy, 30 years old. Typically, I wear decent-quality jeans and a t-shirt. Usually that is a threadless or band-related t-shirt. And I'm pretty comfortable in this.

I'm also single, and would like to dress a little better when I'm out and about. How can I begin to develop some sense of style? Are there some basic tips that I should have learned years ago? Like X with Y looks good, or A with B is a bad idea?

More than happy to help focus this question, but I'm so style-illiterate that this is the best I can do for an opening.
posted by iftheaccidentwill to Clothing, Beauty, & Fashion (13 answers total) 16 users marked this as a favorite
A lot of looking good is simply feeling like you look good. What appeals to you? Plenty of people pull off the jean and t-shirt look, simply because they're confident enough wearing it. Are you unhappy with that look now? Can you think of any look you've seen that you preferred?

What shoes are you wearing? Good shoes are essential. If you want to keep doing the jeans & t-shirt thing, you'll need some good shoes.

Are you a heavy guy, thin guy, tall guy, short guy? The skinny jean and t is only going to work on waifish guys, but almost everyone can pull off the khaki and sweater look. Colors make a difference, too, so consider which ones do and don't look good on you. Depending on your skin tone, there may be colors that you want to avoid, for fear of looking sickly or dead.
posted by Gilbert at 7:48 PM on December 26, 2010 [1 favorite]

The thing I'm teaching my daughters is this: Fashion is a tool you use to signal to others what kind of person you think you are.

The first step to changing your style, therefore, involves deciding what kind of message you want to send.

'More style' could mean dressing up in well-tailored suits every day a la Barney Stinson, or it could mean getting your English professor vests-and-Oxfords mojo on, it could mean channeling your inner Dean Martin... What are you going for, here? Try to think of a bunch of adjectives you'd like people to use in reference to you and hit us with 'em.
posted by Andrhia at 7:48 PM on December 26, 2010 [11 favorites]

Guys have it pretty easy in the fashion department. You don't have to do much to look pulled together.

A stylish light jacket or blazer will usually instantly upgrade any jeans + t-shirt combo. You'll probably have to throw down about $100-200+ but you can wear it with basically anything and you can wear it over and over.

Good fitting designer jeans are also a must. I would go to Nordstrom's Rack or similar so the sticker shock doesn't kill your fashionable aspirations. I prefer dark jeans, but some people feel differently. I would bring a friend with you to tell you what looks good. \

Most guys outfits are basically one of 2 or 3 combinations:

Nice Jeans + Button Down Shirt

Nice Jeans + Button Down Shirt + Blazer or Light Jacket

Nice Jeans + Some Sorta T-Shirt + Blazer or Light Jacket

For all of these add shoes appropriate for venue.

So what it sounds like you need is a few pairs of good designer jeans that fit correctly (if what you already have isn't doing it for you), a stylish light jacket and/or blazer, cool sneakers, and nice leather shoes. And maybe a couple of button downs.

Oh and get a haircut at some place that doesn't cost $15.

And upon looking at your profile and seeing you are in Canada, I would go for the blazer so you can layer with a coat. Get a nice scarf too with matching gloves or leather gloves.
posted by whoaali at 8:04 PM on December 26, 2010

My ex girlfriend had a scrapbook where she pasted anything she thought looked good and could see herself wearing...flipping through this every so often gave her inspiration.
She's got absolutely adorable style.
posted by whalebreath at 8:31 PM on December 26, 2010

I second the scrap booki idea. I save pictures of models with my hair type/skin coloring/face shape for makeup. Also try and for male fashion tips.
posted by figment of my conation at 9:09 PM on December 26, 2010

Don't confuse fashion with style. Fashion's what's popular now (and varies, depending upon your tribe) but Style is much more personal. Style's what sets you apart from your peers.

Good fitting designer jeans are also a must.

But by age 30 you should be expanding your wardrobe to include more than trousers made of denim -- especially, blue denim.
posted by Rash at 10:11 PM on December 26, 2010

Good advice from whoaali and others. Scroll through The Sartorialist and pay attention to the details in pictures that look good to you. You have to train your eye to see how a good "look" works and go in a direction that feels good to you.
posted by Anitanola at 10:54 PM on December 26, 2010

I have several suggestions, having recently undertaken a similar effort to sharpen up my physical presentation.

Go and get the GQ Style Manual. In fact, consider a subscription to GQ. There are certainly lots of other magazines devoted to men's fashion, but in my opinion GQ has the right approach to what style (not just fashion) really is. I totally agree that "style" is very personal; it's all about what you are comfortable in and how you want to present yourself to the world. For many men, like myself, it is useful to have a starting point, a primer on the basics -- which tie knot works best for which collar shirt, how to match patterns, what to look for in quality shoes, etc.

Start reading some "person on the street" fashion blogs. Right now, I don't have access to the computer where I've bookmarked these, but The Sartorialist is an excellent example. These are typically snapshots of real people on the street with a brief commentary about why a particular outfit works or what is unique and eye catching about how the subject dressed themselves. You don't want someone to tell you *what* to wear, you want tips on *how* you should be thinking about your clothes.

You have to try on a lot of clothes. Not all chinos or dress shirts are the same -- the way an article of clothing fits you in particular makes all the difference in the world in how you look. I used to think that all you needed to know was your waist size but now I realize that brand X of jeans just looks so much better on me than brand Y even though they are labeled the same size.

This may or may not apply to you, but for me, getting a little more physically fit made a *huge* difference in terms of dressing with confidence. Yes, being healthier always looks better but I'm not talking about being rail thin or having a swimmer's build; it has more to do with the way you feel about your body and appearance and wearing clothes that are eye catching and not hiding behind them.

For formal clothes and sport coats, you need a good tailor. These clothes need to fit really really well, and these days the general rule is snug.

Many times you can find great clothes that fit your style well inexpensively or on sale, but recognize that there are certain articles that you will wear frequently enough and for long enough that you will appreciate spending extra money. A nice watch. High quality dress shoes.

Finally, and this is the thing I struggle most with, you need to plan on putting some thought into how you get dressed in the morning. This is the classic "I-have-a-closet-full-of clothes-and-nothing-to-wear" problem. My natural tendency is to wear the same 5 or 6 favorite articles of clothing and in the same combinations. Now, before I get dressed, I like to ask myself: how do I feel today? Am I a super cool young rock star that wants to shock people or am I a conservative older man that wants to command respect? Am I a weekend dad dressing for comfort or am I a California surfer dude without a care in the world? Am I hung over and just want to get through the day without attracting attention or do I need to convey something in particular about myself today? I will then start by picking out one article of clothing that really represents the kind of person I feel like that day. Then I pick out all the other clothes that work with the first article, consciously trying to avoid combinations I've used before.

I certainly wouldn't hold myself up as a particularly fashionable person, but I have been working on it more for the last year or so. It's a process, more about changing how I think about my appearance rather than going out once and dropping a ton of money on new fancier clothes. It's a good, worthwhile thing to do. Yeah, you don't want to focus too much on superficial appearances, but it's good to control the impression you leave on people, and it's good to feel confident out in public.
posted by Slarty Bartfast at 12:16 AM on December 27, 2010 [1 favorite]

First, a few tips:

To make it easier on yourself, find a color palette you like, and add items to your wardrobe that fit somewhere in it. It will make dressing easier, and you're more likely to look subtly coordinated.

Accessories. Yes, accessories. These are the little details that add to your style. A nice belt, quality t-shirts in your color palette (for under sweaters and button-down shirts), good shoes (not shoes you'd wear when working out), and even nice socks and underwear!

Although I mention it above, a belt is key. Find one with a simple but stylish belt buckle, and decent quality leather.

Fit is important. If you don't feel comfortable in an item, and it doesn't look great on you, don't buy it. Try everything on. (Well, not underwear.) Make sure things aren't slouchy, and that they layer nicely.

Now, a couple of examples from real life. You might want to observse stylish men around you to see what they wear, too.

Mr. metarkest is an artist with an outdoorsy bent. He almost always wears blue jeans, but is particular about the shade and finish: slightly stone washed, about a medium-dark shade. His color palette primarily consists of chocolate browns and olive and forest greens, but occasionally he adds something mustard colored or a dark brick red. He always wears brown shoes and a brown belt. His undershirts are usually muted, heathered shades that look good with whatever's going over them, which is a button down shirt, a v-neck sweater, or a zip front sweater. He is very particular about sweater details - nothing that tapers in toward the bottom, for example.

Friend A is an artist/designer. His color palette is blues and greys. He wears jeans with a more modern finish, a black belt, and black shoes. He has a nicely designed watch. In general, he goes for a crisper, more urban chic look than Mr. metarkest, so all of his shirts are a finer weave with crisper collars. All of his undershirts are a crisp white or a true grey, not a heather grey.
posted by metarkest at 5:30 AM on December 27, 2010

For clothing ideas, I really like An Affordable Wardrobe, a blog by a guy out in the Northeast who thrifts a lot of old-school vaguely preppy stuff. He's really informative about thrifting, fit and quality, plus he has a good eye.. I've linked to a jeans-and sweater outfit of his.

What do you usually do? I get around by bike, for example, so all my work clothes have to be sturdy yet office-appropriate and washable--cotton pants, button-downs and sweaters for me, plus suede oxfords for summer and heavy oxfords or lace-up boots for winter. If I drove, I'd break out the wool pants and more citified shoes.

What's your work/school environment like? What do the better-dressed people there wear? Unless you want to be known for your dandyism (perfectly acceptable!) think about modelling your work/school clothes on that. Here are some (slightly too inflexible) posts on business casual from Put This On.

Put some thought into shoes. Good leather shoes are relatively non-puffy/soft in shape, are leather-lined to the toe and have sewn-on soles. (A currently fashionable, decent quality, easy-to-find shoe is the Clark's desert boot/chukka--a bit ubiquitous, but a good starter shoe.) Good sneakers for general wear (disregard this if you're really really into sneakers) are usually classics--purcells and converse, for example.

If I had to build a wardrobe cheaply from scratch, this is what I'd do (assuming that you, like me, work in a relatively casual place):

Figure out my shoes, since they're an everyday item--can I afford really good English or Italian shoes, new or used? Do I want to thrift around until I find some good-quality leather shoes? If not, buy a pair of Clarks chukkas in a non-suede, maybe at discount on Ebay--or else a pair of leather Purcells. If I needed winter leather boots, I'd look at the army-navy store and try for some old-school dressier leather combat boots. I'd pick up a pair of canvas Purcells for summer, too--possibly in a striped canvas.

I'd thrift around a lot looking for cotton pants that I liked. If I had the money, I'd have them professionally altered. If not, I'd hem them carefully myself, relying on the fact that most people won't notice a minor imperfection. I'd avoid head-to-toe black--avoid black pants in general for casual clothes. Dark grey or olive are better.

I'd try to thrift shirts that button rather than polos or cotton sweaters. I'd aim for softer, more casual fabrics and try to pull them out of the dryer while warm and then hang them, minimizing ironing. Again, I'd avoid black--it fades badly and is difficult to match. If I was uncertain, I'd avoid bright patterns in unusual colors.

I'd look for some good, woolly sweaters, probably on Ebay (sweaters are more forgiving fit-wise, plus I never see good ones at the thrift store). Stripes, solids, marls are all good.

I'd keep my eyes open for a good sport coat or two in a tweed or a corduroy, making sure not to just buy the top half of a suit.

I'd get a brown leather belt and a black leather belt. I'd recognize that wearing my shirts untucked is a definite look, not a default position, so I'd make sure that my shirts looked good untucked if I wanted to go that route.

If I were uncertain about anything, I'd buy the most classic thing I could find.
posted by Frowner at 7:01 AM on December 27, 2010 [1 favorite]

The one thing I have done that has had the biggest impact:

I wear things that fit tighter than I used to be comfortable with - my shirts are fitted, my jeans are skinny, my slacks are hemmed to the proper length (they come up a little when I sit).
posted by jander03 at 8:19 AM on December 27, 2010

Response by poster: Thank-you so much, all, for the advice! In answer to a few questions above: I'm a thinner/athletic guy, on the shorter side (5' 8"), and I work as a teacher in an elementary school. The dress code at my school goes from one extreme to the other.
posted by iftheaccidentwill at 10:30 AM on December 27, 2010

The best piece of fashion advice I ever got was, ironically, something I figured out on my own: I needed to stop trusting my own opinions when it came to buying clothes. Most people foolishly assume they know what looks best on them. And they're wrong. That's a major reason why you see people wear boring or ugly things. For whatever reason, they think "This looks good on me" or "This is what I look like." And They're Wrong.

What you need to do is find someone a woman who has style and go shopping with her. Find someone who will tell you what SHE thinks rather than tell you what she thinks you will like.

Have her pick what you should be wearing, and - even if you don't like it, always try it on. Bring a point & shoot camera. Have her snap pictures of you in the clothes, always including the ones you don't buy. What you're trying to do is to teach yourself what looks good on you. Pictures work better because the mirror lies.

There's a trick your mind plays when you look in a mirror. It's harder to judge what you see because you're there at that moment and still IN the moment. You're emotionally invested in the moment because it's YOU, there and then. It's too easy to see what you expect to see when you look in a mirror. If you think a shirt won't look good on you, you're more likely to decide that it doesn't look good even if it looks GREAT. Still pictures are completely different. Yes, you're still looking at 'you', but you're far less emotionally invested in what you see. Maybe because the moment has passed, which means you can't fix it or change it? Maybe. All I know is this: if you put on a shirt you don't think you like and you look in a mirror, you'll see yourself in a shirt that doesn't look good on you. On the other hand, if you see a photo of yourself in that same shirt, it's a lot easier to see it for what it really is rather than seeing what you expect to see.

After a while, as you get used to seeing yourself in better clothes, you'll get better at buying better clothes.

So... my secret weapon is shopping with female friends. Confident female friends are the best! I want women who tell me what THEY think rather than tell me what they think I want to hear.

Beyond that, I'll echo comments above about Clothes That Fit. Look for fitted shirts. NEVER regular. Always fitted. Look for pants and jeans that fit. Ignore those stupid skinny jeans. They look dumb and you know it, but it's equally important to IGNORE RELAXED FIT TOO. They're baggy and will make you look like a frump.

I wear a lot of dark striped fitted button down shirts and dark jeans. Simple but comfortable black dress shoes. I pair that look up with a dressy coat. I often get comments from women about how well I dress and I think it's funny because I don't wear anything today that I would have bought five years ago.
posted by 2oh1 at 2:56 PM on December 27, 2010 [1 favorite]

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