Newbie Fashion Tips for Grown-Up Men

Just over a month ago, I ran in­to a friend at a CES event. While I see this friend around town once in a while, this was the first time I’d seen him in a non-ca­su­al sett­ing since Blog­world 4 months ear­li­er. Af­ter exchang­ing the usu­al pleas­an­tries, he asked me an odd ques­tion: “Is this like your con­fer­ence par­ty out­fit?”

In­deed, I was wear­ing the ex­act same cloth­es I’d worn to the event four months ear­li­er. Since he doesn’t usu­al­ly see me dressed up, it stood out enough for him to re­mem­ber. But that’s not the re­al point, here; the re­al point is that I have few cloth­es suit­able for “adult” gather­ings.

I have a suit, of course, for wed­d­ings and fun­er­als. (I haven’t had a job in­ter­view in 9 years, but if I did, it would be suit­able for that, too.) And I have my day-to-day cloth­es, which aren’t aw­ful but which aren’t any­thing to brag about, ei­ther. Func­tio­n­al ca­su­al, ba­si­cal­ly: jeans and khakis, an as­sort­ment of but­ton-front shirts, some cot­ton sweaters.

As a col­lege pro­fes­sor, there’s not a lot of pres­sure on me to dress up. If any­thing, it’s just the op­po­site. For one thing, I in­ter­act reg­u­lar­ly with younger peo­ple, most­ly tee­nagers (I teach 100-lev­el cours­es), and be­ing too for­mal cre­ates a bar­ri­er be­tween my stu­dents and me. That might be ok in busi­ness or law (think John House­man in Pa­per Chase) but for my class­es and my teach­ing style, some lev­el of rap­port is cru­cial. For another thing, my fel­low pro­fes­sors don’t ex­act­ly set the sar­to­rial bar very high – and there’s a cer­tain sense of bo­hemian “me-against-The-Ma­chine” at­ti­tude ex­pressed by vi­o­lat­ing “cor­po­rate” stan­dards of dress.

But most­ly I dress the way I do be­cause I’ve nev­er re­al­ly learned how to dress other­wise. Like a lot of my fel­low geeks, fashion just wasn’t on the ra­dar for me. For­tu­nate­ly I have a brother who has al­ways been very fashion-con­s­cious, and he’d take me in hand ev­ery few years when my fashion sense got too out of touch with rea­son and so­cial ac­cept­a­bil­i­ty.

Well, my friend’s off-hand com­ment was a wake-up call for me. I mean, I’m a grown man – I should have more than one pair of slacks and one shirt nice enough to wear to an in­dus­try event with­out em­bar­rass­ing my­self! So I set out to ed­u­cate my­self on some fashion ba­sics – what shoes go with what kind of trousers, how to distin­guish vari­ous sorts of dress shirts, and so on.

I did what any true-blood­ed geek does when he or she wants to find out about a new top­ic: I goo­gled it. But what I found was scat­tered, of­ten con­tra­dic­to­ry, and for a new­bie like me, down­right con­fus­ing. A lot of the in­for­ma­tion out there is tied to spe­cif­ic so­cial con­texts: the work­place, the night­club, and dat­ing, main­ly. And a lot of it’s quite vague – the an­sw­er to most ques­tions is “it de­pends on your per­so­n­al style” which I’m sure it does, but what if you don’t know your per­so­n­al style yet?!

With some per­se­v­er­ance, a few trips to de­part­ment stores, and the help of friends on Twit­ter, I ma­n­aged to as­sem­ble the fol­low­ing rules. As with all rules, they’re meant to be bro­ken – but on­ly by peo­ple who know how to break them. For the rest of us, this is a pret­ty good primer on ba­sic men’s fashion.

Dress Suits
1. You even­tu­al­ly want to own three suits. Your first suit should be ei­ther navy blue or gray, pos­si­b­ly with a light chalk stripe (like a pin­stripe, but soft­er), and in an all-sea­son, medi­um weight. Ei­ther of th­ese col­ors will fit in­to most so­cial sett­ings. Your se­cond suit should be the one you didn’t get the first time around. Your third should be black – not for fun­er­als, but for black tie af­fairs. If you work in a field where suits are the norm, you’ll prob­a­b­ly want more than three; once you’ve cov­ered the ba­sics, you can move on to more dist­inc­tive suits (pin­stripes, dif­fer­ent weights, un­con­ven­tio­n­al col­ors, etc.).

2. Suits are made of wool or cot­ton. High­er thread counts sig­ni­fy high­er qual­i­ty, but are iron­i­cal­ly not as durable, so stick with some­thing mid-range. Ask the sales­per­son to help you with this. (Yes, ask the sales­per­son. Suits are not self-serve.) Syn­thet­ic fibers need not ap­p­ly.

3. You nev­er but­ton the bot­tom but­ton. Ap­par­ent­ly, Ed­ward VII got fat and couldn’t but­ton his vest over his bel­ly, so now no­body does. On a three-but­ton jack­et, you but­ton the mid­dle; the top but­ton is op­tio­n­al. If you have a jack­et with 4 or more but­ton, you ob­vi­ous­ly know what you’re do­ing al­ready.

4. A gentle­man car­ries a hand­k­erchief in his front breast pock­et. You don’t have to get fan­cy, just fold it square to fit and have 1/4” to 1/2” stick­ing out the top. Then prof­fer it as need­ed. And wash it af­ter.

Shirts
1. Don’t wear your sleeves too short or too long. 1/4” to 1/2” of cuff should show be­yond your jack­et sleeve.

2. Shirts with but­ton-down col­lars are not dress shirts. They’re sports shirts, so wear them with a sports coat. Po­lo play­ers used to but­ton their col­lars down so they wouldn’t flap up in their face while they played. (Are you be­gin­n­ing to sense a theme here? Fashion rules are large­ly dic­tat­ed by what En­glish gentle­man and no­bil­i­ty did gen­er­a­tions or even cen­turies ago. Sports coats? You wore them dur­ing sport, i.e. hunt­ing. Reg­i­men­tal stripes on ties? They in­di­cat­ed your reg­i­ment in the Bri­tish mil­i­tary. And so on.)

3. If you un­but­ton your col­lar, re­move your tie. You can wear a suit or sports coat with­out a tie – just ask Oba­ma – but wear­ing a tie with an un­but­toned shirt looks slop­py.

4. You can un­but­ton the top but­ton al­ways (pro­vid­ed you’re not wear­ing a tie), the se­cond but­ton usu­al­ly, the third but­ton on­ly on dis­co night at the Rollera­ma.

Trousers
1. Wear your pants at your na­t­u­ral waist. Too high and you look like Gram­pa, too low and you look like a high school kid. Your waist­band should sit 2-3 inch­es be­low your bel­ly but­ton.

2. Pants should al­most touch the ground with­out your shoes on. Jeans can be a lit­tle longer, since they shrink a bit when you wash them.

3. One pleat, max­i­mum. If you’re a big guy, like I am, you learned some­where along the line that pleats are slim­ming. They’re not. At best, they look like you’re a big guy try­ing to look slim­mer; at worst, they ac­tu­al­ly make you look heavi­er be­cause they pull out across you, broa­d­en­ing your ap­pear­ance. In any case, the job of a pleat is to main­tain that crease sown the front of your pants. For pants with­out that crease (and many with it), pleats are un­ne­ces­sary; for pants that need the pleat, they on­ly need one.

4. 1” to 1 1/2” cuffs. Or not. There’s noth­ing wrong with cuffs, there’s noth­ing wrong with no cuffs. They are un­der­s­tood, how­ev­er, to be an old­er man’s style – not in a bad way, think so­phis­ti­cat­ed, ex­pe­ri­enced, distin­guished, and conser­va­tive. For younger men, a clean­er line is gen­er­al­ly pre­ferred.

5. A use­ful piece of trivia for the Amer­i­can abroad: in Bri­tish En­glish, “pants” are un­der­wear. So if, for in­s­tance, you are in Lon­don and get in­vit­ed out and maybe your trousers are dir­ty from work, don’t say “I’d love to go out, I just need to go home and change my pants first.” And if some­one should ask, “Why, are your pants dir­ty?”, don’t say, “Yeah, I al­ways get my pants dir­ty at work.” You will be laughed at. Er, I as­sume.

Shoes
1. Pay at­ten­tion to your shoes. Ev­ery­one else does. It’s hard for the non-fashion-maven to tell a more ex­pen­sive suit from a less ex­pen­sive one, a high-qual­i­ty shirt from a medi­um-qual­i­ty one, and so on. But ev­ery­one can tell cheap or poor­ly cared-for shoes. Buy the best ones you can af­ford, and take care of them. Pol­ish them reg­u­lar­ly (a few swipes with a wax-in­fused pol­ish­ing cloth is of­ten all it takes) and store them cov­ered if you won’t be wear­ing them for a long time. Shoe trees, it turns out, are im­por­tant: they not on­ly hold the shape of the shoe but the ce­dar ones ab­sorb mois­ture (and thus odors) which helps pre­serve the leather. (Aside: wo­m­en tend to pay a lot of at­ten­tion to men’s shoes. Keep that in mind when a) dat­ing, and b) in­ter­view­ing for a job.)

2. Shoes are made of leather (be­sides sneak­ers). Any­thing not made of leather you can con­sid­er a non-shoe. Leather breath­es and adapts to the shape of your foot. The soles don’t have to be leather, but the up­pers do. (True sto­ry: as a young man, my brother was a car sales­man here in Ve­gas. In the sum­mer, the tar­mac could get well over 150 de­grees F. Stand­ing out there with leather-soled shoes could give you se­cond-de­gree burns! So they wore rub­ber soles, which melt­ed af­ter a month or two and had to be re­placed.)

3. You need more than one pair of shoes, but not too much more. Black ox­fords (lace-up dress shoes), black loafers (slip-on shoes), brown ox­fords or loafers, and you’re set (not count­ing your ath­let­ic shoes, of course). A pair of an­k­le-high boots in black or brown can sub­sti­tute for the loafers. Ox-blood (bur­gundy) shoes are hard­er to find but in the­o­ry go with ev­ery­thing. You can pret­ty safe­ly ig­nore white shoes.

4. The shini­er the shoe, the dressi­er. Matte-fin­ish shoes – nubuck (that peb­b­ly leather), suede, and dis­tressed leather shoes are au­to­mat­i­cal­ly com­pat­i­ble with jeans or khakis; shini­er shoes might still go with jeans but it de­pends on the rest of your out­fit, the dressi­er you are the shini­er your shoes can be. If you can wear them with a suit, you prob­a­b­ly can’t wear them with jeans, and vice ver­sa.

5. Shoes should be the same tone or dark­er than your pants. This is all the rule you need to know when try­ing to fig­ure out what shoes to wear. This is why you nev­er wear brown shoes with black trousers, but you can usu­al­ly wear black shoes with brown trousers. When in doubt, wear black.

Ac­ces­sories
1. Match your belt to your shoes. It doesn’t have to be a per­fect match, as long as you wear a black belt with black shoes and a brown belt with brown shoes.

2. Match your socks to your pants. Again, it doesn’t have to be a per­fect match – a lit­tle lighter or dark­er is fine. If you don’t have socks to match your pants, you can match your shoes, or just wear black socks.

3. White socks are for sports. On­ly. Un­less you are a) wear­ing sneak­ers, and b) do­ing some­thing ath­let­ic in them, avoid white socks.

4. Your tie should reach your belt. Any­thing short of your belt makes you look like a rube.

5. Try a front-pock­et wal­let or mon­ey clip. This will save wear-and-tear on your back pock­et (help­ing to avoid the heart­break of “butt­square”), help avoid pick­pock­ets (a lit­tle – the good ones know…), and save your back. Plus: classy!

6. You’re al­lowed one af­fec­ta­tion. A fe­do­ra. A pock­et watch. A bracelet or class ring. A vest (if you’re not wear­ing a three-piece suit). An ex­pen­sive wrist­watch. Pick one, but no more – give your what­ev­er-it-is space to say what­ev­er-it-says.

If it feels like th­ese rules are ar­bi­trary and sti­fling, they are. Think of it like learn­ing how to paint: first, you do a still-life (ar­bi­trary) us­ing just one col­or (sti­fling). Even­tu­al­ly you move up to two and three col­ors, then maybe a warm or cool palette, and your sub­jects might ex­pand to in­clude fig­ures or land­s­capes. Once you’ve mas­tered the ba­sics, you can be­gin to press against the rules, jux­ta­pos­ing non-com­ple­men­tary col­ors or paint­ing un­con­ven­tio­n­al sub­jects.

In fashion as in art – style emerges not from a lack of rules but from a mas­tery of them, from mak­ing them serve you in­stead of the other way around. If you’re a geek like me, you need to dial a fresh start – clear your clos­ets of all those con­fer­ence free­bie t-shirts, put a shine on your shoes, and burn your butt-crack pants. Ul­ti­mate­ly, th­ese rules are not at all about tamp­ing down your per­so­n­al­i­ty but about learn­ing how to ex­press it. And un­fair as it is, peo­ple will take you more se­ri­ous­ly when you dress with a mod­icum of style.