Creating a grown up wardrobe

Hi, my name is NotAiden and I am a shopaholic.

I.  Love.  Clothes.  Always have, I just love matching textures and colours and creating a unique outfit.  However, when I came out I had no idea about how to build a professional man’s wardrobe.  Professional woman sure, but man?  Don’t you just throw on a button shirt and coat and be done with it?  Besides, I could never wear any of that tailored stuff, my boobs would show!  For years I stuck with a slightly modified version of the traditional transman uniform: polo shirt, jeans, sneakers.  My polo was plain coloured and worn tighter than any self-respecting straight boy would consider, my jeans were hip huggers, and my sneakers had never seen athletic work of any kind, but I still dressed like a college kid.  Just a gay college kid.

Then I started working in a place that absolutely, 100% required dress shirt and slacks.  I cannot begin to tell you how bad I looked.  Bright shirts in a way that screamed “send me back to the 80s!” instead of the “yeah, I’m gay, so what?” look I was going for.  A couple of years after that and I’m suddenly giving presentations to new grads about how to dress professionally.  How on earth did I get here?  I have no idea, but while I was talking to all these guys who aren’t that much younger than me I realised that a lot of what I was saying would be useful to trans guys — particularly those of us who are in professional environments or about to be.  College kids and those of you in more creative fields can ignore this, your dress rules are different.

Let’s start with the basics.  All of these are a bit boring and will probably make most of you go “but I want to express myself!”  Don’t worry, they’re just the foundation.  Once you have these taken care of you can start adding pieces that are trendy or unique.

First up: a basic white dress shirt.  Yes, it’s dull.  It’s also classic.  Every guy needs a white cotton dress shirt in his closet.  Why?  So that when the great guy your best friend set you up with says he’s made reservations at a restaurant that has a dress code (and is WAY out of your price range) you don’t have to run out and hope you find one at 3AM.

Details: Plain white cotton.  No polyester or silk, no peaking, no button down collars, no stripes, nothing.  You want this to be so basic that you barely even notice it.  That way it goes with everything.  Cuff type is up to you, but I recommend standard button because that way it can be paired with a sweater.  I love French cuffs (cuff links = more accessories) so I have two versions of this with different cuffs.  The button cuff is for sweaters and slightly more traditional events, the French cuff is for everything else.

Fit: See this picture?  It’s perfect.  If you’re slim and post-top or really small chested, go ahead and get yours a bit tighter.  Just be aware that you may need to replace it more quickly than you’d like, especially if you’re currently pre-T.  Do NOT buy a shirt that you can “grow into”.  We’re not children any more, our clothes should fit properly.  There is very little that looks more sloppy than a grown man in a dress shirt a size too large for him.  Other major don’t: NEVER wear this shirt untucked.  Jeans, khakis, dress slacks, doesn’t matter.  Tuck in your shirt.

What are you wearing with that shirt?  A pair of flat front grey trousers.  Not jeans (not for that expensive restaurant anyway), not black trousers, certainly not shorts.  Why not black?  It’s not versatile enough and too formal for many occasions.  Grey can go from business casual to formal and be paired with brown and navy, you can’t do that with black.

Details: Flat front.  Slate to charcoal (yes, those are different colours).  Lightweight wool.  No cuff unless you’re tall.  This is another item that you barely notice.  If after you’ve been on T a few years (or if you’re not planning on starting T in the near future) you find a brand that fits well and comes in several different shades of grey I suggest snatching them all up at once.  A good pair of dress trousers is worth gold, especially in the pre-T years when you’re trying to mask a female body type.

Fit: Again, look at the picture.  They’re not falling off his ass, but they’re also not so snug you can see his balls.  You want a pair that will just rest where they need to be without a belt.  Notice that this man does have a bit of hip and butt.  Not a huge amount, most of us probably have more pre-T, but he’s not a perfectly straight line either.  It’s not until you get down past his butt that his trousers shift to hanging straight down.  They’ll continue to go until they hit his ankle where they will make ONE clean crease as they connect to the top of his shoe.  If you’re not sure about length err on the side of long and find a good tailor.

Ok, you’ve got your shirt and trousers picked out, now what?  It’s spring and a bit chilly outside?  Well that’s why you have a selection of sweaters in your closet.  I like cashmere, but if you can’t afford that (I can’t always) there’s also your standard acrylic, wool, and poly-cotton blend.

Details: Single colour.  Lightweight.  Crewneck.  Have at least one grey, one black, one navy, and one brown, the other colours are up to you.  I have a HUGE selection of sweaters because they’re an easy way to change the tone of an outfit.  Spring Pride planning?  Baby pink.  Christmas dinner?  Cranberry red.  Shabbat service?  Sky blue.  Ribbing, different neck styles, and a rainbow of colours are all fine here, that’s why we’re wearing neutrals for our slacks and shirt.

Fit: Loose enough to not show odd creases over your dress shirt, but tight enough to fit nicely under a blazer.  Once again, the picture is about right (are we sensing a pattern here?).  Sleeves should still comfortably reach your wrists when your arms are extended, but not go past the crease where your thumb meets your hand.  Wear your nice shirt when you go try these on, that way you don’t come home with a bunch of wrong sizes.  (Oh, and don’t wash your cashmere sweaters, their lifespan increases drastically if you dry clean them.)

Alright, second date time.  This time you’re going somewhere a bit more casual first, maybe to a movie or nice little cafe in the arts district.  You don’t want to be too dressy, but you want to look nice.  This is where your jeans come in.

Details: Semi-dark wash.  Boot cut.  Bit of fading and whiskering at the hips and thighs.  Why boot cut?  It looks good on just about everyone without being too casual.  It’s classic, but also trendy, if you look at older celebrities (and by ‘older’ I mean above 25-30) you’ll notice that they mostly wear medium to dark boot cut jeans.  The fading and whiskering make them look comfortable with a t-shirt, but still dressy enough to be paired with your nice shirt.

Fit: Snug around the hips and butt, slim through the knee, loose from knee down.  There’s also a style called “relaxed boot cut” or “casual boot cut” that works very well for guys who are either thick (muscular, heavy, or big boned, doesn’t much make a difference in jeans) or gangly because it allows for a bit more room in the seat.  Should rest just below your navel, touch lower if you’re pre-T and need to mask womanly hips.  Other than that, just make sure the bottoms don’t drag on the ground when you walk.  If you’re short (like me) you can take longer jeans into your tailor and ask that that they keep the bottom seam when they’re adjusting the length.  This is another where I suggest snatching up every pair you can afford once you find a brand and size that fits well.  Jeans change so often that it can be difficult to find the right ones even a year later.

Between the jeans and white shirt you’re all set for a cafe, but what if after that you guys are going to see a bit of community theatre?  Jeans are a bit casual so you’ll need to dress them up with more than a shirt and sweater.  Luckily, you own a black blazer.

Details: Black.  Three button.  Lightweight wool.  Single breasted.  No pattern, stripes, obvious buttons, or other accenting.  If you want to go crazy with your other blazers go right ahead, but you should have at least one boring type in your closet.  I suggest also having a navy and a grey for different occasions, but black will dress up jeans better.  Three buttons help with that and also look good on just about everyone.

Fit: Slim, but loose enough to go over a sweater.  You want there to be just the tiniest bit of shirt peeking past the cuffs when you bend your arm.  See the picture for an idea and if you’re not sure go to a good suit/tuxedo store for a fitting.  If you’re pre-T and get funny looks pretend you’re 12 and being sent to a fancy boarding school.  (No, seriously, the conversations alone are worth it.)  Never button the bottom button, always do the middle one (when standing, when seated you unbutton it), and do the top if you like the way it looks.  Never put your coat on the back of your chair unless you plan on never resting against it.  Majority of people won’t notice, but the most posh will see it as a sign of poor breeding and it’ll put horrible wrinkles in the fabric.  If you’re warm there are coat checks for just this reason.

You’ve gone on two dates with this guy, but now you have to go away for a weekend (sorry) to see your brother get married.  Obviously you’re going to need a suit.  You don’t want black because that’s usually for funerals, it’s a spring wedding so navy is a bit dark, but tan is a bit light, and you’re certainly not going to wear white.  In comes the classic grey suit.

Details: Single breasted.  Two or three button.  Lightweight wool.  Plain as you can get.  This is the least offensive, easiest to forget suit you can find.  Presidents and Prime Ministers wear various shades of grey for a reason.  You want to look like your suit could just as easily be worn today or in 1912.  If you don’t have many reasons to wear a suit you can get a coat in the same fabric as your grey trousers instead.  If you’re going to wear suits often I suggest having at least a light and dark grey in addition to your pinstripes, blacks, navies, etc.  If you really like the dressed up look get three piece suits so you can opt for or against the vest (waistcoat to the non-Americans).

Fit: Tailored.  Go and get fitted, it’s worth the money and you usually get a discount on whatever you buy that day.  Scope out a few places first though, you want to see well dressed businessmen making up most of the clientele.  American or Euro cut is up to you, I opt for three-piece Italian because I’m a snob and American cuts make me look bulky.  Once again, never do up the last button on your coat.  On a vest it’s optional, but most people skip it so they have a bit more moving room.

These next few are largely US-centric, though I’ve seen an Englishman here and there wear them as well.  Not so much with the French and Danish guys so if you live outside the US check out your local men before buying anything.

First we have the classic khaki/light coloured chino.  These are for casual office days, family picnics, and any other time you want to be dressier than jeans, but more casual than wool.

Details: Flat front.  Light to dark tan.  I suggest a colour darker than this and closer to what you’d find at Old Navy if you’re only going to have one pair.  This light and you really don’t want to wear them pre-Easter or post-Labour Day, it looks a bit silly.

Fit: Same as your grey trousers.  You can wear these a teeny tiny bit longer than dress trousers, but I prefer to err on the side of dressy just in case I need to wear them somewhere I need to be impressive.  Just make sure they’re not too tight, khakis show off an overly-large bulge much easier than jeans and usually a bit easier than dress trousers.  You don’t want to look like you’ve got an erection at the company picnic.

A good pair of knee-length shorts are essential for most US summers and many US springs.  Hell, I needed these for a few winters in California.  Khaki is a good colour that goes with everything and can be either “dressy” (for those company picnics you don’t have an erection at) or casual.  Just please don’t wear them on your European tour, you make the rest of us look frumpy.

Details: Flat front.  Khaki, olive, or tan.  Knee-length.  The rest is all about personal preference.  I know guys who love these shorts, but I wouldn’t buy them because I like mine to look good even when they’re all crumpled because I left them in the dryer for three days.

Fit: As long as they cover your ass and come to your knees (no lower!) you’re fine.  One of the advantages to shorts is that they’re considered casual wear so there aren’t as many rules to follow.

Yes, that is the dreaded polo shirt.  I want you to notice a few things though.  It’s plain.  It’s worn without an under-shirt.  It’s well fitted.  It’s tucked in.  This is how well-dressed adult men wear their polo shirts.  The only time this rule is not applied is when the shirt is worn with casual shorts (like my rumpled ones).  You don’t wear a polo shirt with jeans therefore you never have to worry about whether or not to tuck it in.

Details: Get a black one and then pick your favourite colours.  I have a baby pink and a turquoise blue.  If you wear polo shirts more often you’ll want to get more, but my job requires dress shirt and slacks so I don’t have need for many.

Fit: Like the picture, generally.  Sleeves shouldn’t go past the elbow, stomach and chest shouldn’t stretch, and it should be long enough to tuck in.  The major exception to this is if you never need to wear one with slacks.  The only time I wear my polo shirts are when I’m also wearing shorts so mine are all fit to rest just below my belt line.

Now we move on to the finishing details: coats, shoes, belts, and one more sweater.  We’ll start with what you’re wearing with your nice grey trousers and suit: black dress shoes.

Details: Black.  Slip on.  Leather (or faux-leather if you’re vegan).  Why black?  They can be both dressy and semi-casual so you don’t have to worry about whether to wear black or brown to that dinner with your boyfriend’s boss.  The slip on is for the same reason.  These are actually a bit more formal than I would recommend for a foundation pair, but they’re just so pretty.

Fit: …You do know how to buy shoes, right?  This is one of those things that doesn’t really change based on sex.  They either fit or they don’t.  Snug enough to stay on, but loose enough that they don’t hurt your feet.  There are charts and weird measuring thingies.

Obviously you need something to keep up your trousers and suspenders/bracers went out in the 50s.  This is why you will own a basic black, leather (or faux-leather), silver buckled belt.

Details: This exact belt.  It’s so classic that you can find one at about every clothing store in the world.  I don’t care what your other belts look like, you should have at least one like this.  Why?  Because it goes with everything from your suit to your khaki shorts.  If you want one with a hidden buckle or braided leather you can get that too, but make sure you have this first.  Otherwise you’ll be trying to find a belt that doesn’t dress down your suit or dress up your jeans and end up having to make a midnight trip to Target.

Fit: It should.

If you live in a warm climate you can ignore this one.  For the rest of us, this is an example of an appropriate coat to go with your suit and/or dress trousers.   It’s warm, it’s classy, it goes with jeans as well as slacks, it won’t be out of style by next winter.

Details: Black.  Wool.  No embellishments, fancy buttons, or anything else that would make it stand out.  You want a coat that’s easy to mistake for someone else’s when you’re grabbing it off the rack.  I always opt for a pea coat because I think they look cool and I have the long arms and legs to pull it off.  Most shorter guys will want to go with a single breasted option, same with wider guys.  If you’re tall and lean you can get away with most anything.

Fit: Large enough to go over a suit coat, but slim enough so you don’t look like you stole it from a 300 pound sailor.  Like everything else, the picture is a great example.

For the times when you want to dress down your jeans and khakis or dress up your shorts you’ll want a pair of brown athletic oxfords.  They’re nicer than sneakers, but more casual than your dress shoes.  And if you need to you can run a heck of a lot faster in them.

Details: Brown.  Versatile.  Lace-up.  You want these to be able to go from a Saturday morning meeting to your niece’s soccer game without looking out of place.  I just bought myself this exact pair, but if you want to go even more versatile you could get something more like these.  Still casual enough for jeans, khakis, and most shorts, but you could also wear them to dress down your grey trousers (but not your suit!) which isn’t something you could easily do with the shoes pictured.

Fit: They’re shoes.  They should fit like shoes.  One special note though: if you’re wearing these with a belt the belt should be brown.  Always match your shoes and belt.  It’s one of those stupid little rules that people notice subconsciously.

Other things you should have, but lack real “rules”:

– Sandals to wear with your shorts.  Not Birkenstocks or the cheap, plastic and foam things you get at the dollar store.  Grown man sandals.  Leather/faux-leather, brown, and dressy enough to wear to company barbeque.  I opt for a more closed style because I always manage to lose them if there’s not a strap in the back, but go with what makes you comfortable.

– Swim trunks.  If you’re pre-top add a rash guard as well.  If you just want a classic type that blends in go with a solid coloured pair that hits near the knee.  If you’re me and you like freaking out the HRC crowd you can get a hot pink, glittery booty short style.

– Casual sweaters.  Note that I said sweaters, not hoodies.  You want something that’ll look appropriate with your dress slacks and khakis.  No, college and/or team sweatshirts do not count.  I prefer military styles in grey and navy, other guys like cable knits and fisherman sweaters.

– Whatever it is you want to wear for lounging around your house on the weekends.  I am a complete and total slob when I don’t have to leave my apartment.  I will spend all weekend in my underwear if I can get away with it.

And the final rule: break the rules.  These are just basics, they should take up a teeny tiny portion of your closet.  I have pinstripe suits, button shirts with graphic designs, belts made from silk ties, and a million other things that wouldn’t be put on here because they’re trendy and artistic instead of timeless and classic.  I rarely wear my polo shirts or shorts and I don’t even own a pair of khakis because my job and home life don’t give me reasons to.  However, I wear black dress shirts with some sort of embellishment almost every day for work.  Use this as a barometer instead of checklist.