Most of these things I have learned from experience, so they apply to small, masculine dandies. If you are large, feminine, or not interested in being overdressed for every occasion, many of these tips will not apply to you, but perhaps there is an aspiring dandy in your life who might find them useful.
Shirts: the foundation of dandyism
- It’s hard to find shirts that fit. Men’s sizes rarely go small enough, and boys’ shirts have the strangest proportions and are usually not good quality. You could wear t-shirts and hoodies every day, but that is not how you roll. So when you find a shirt that fits, get three. (In different colors, obviously.)
- Some shirts have button-down collars, which means that there are tiny buttons holding the points of the collar to the shirt. I hate these, so I never buy them, but if you do buy them, be aware that you must always leave the buttons done. Unbuttoning them looks ridiculous. The only time you undo them is when you are putting on your tie; button them back up immediately when you’re finished.
- If your sleeves are too long, roll them up. It looks classy to roll them up to anywhere on the forearm, below the elbow. If you roll them up above your elbow, you move into preppy territory. It’s your choice, so choose mindfully.
- When not wearing a tie, leave the very top button undone (unless you are emulating Elementary Sherlock). When wearing an undershirt or binder, don’t unbutton any more, because you don’t want anything to show (t-shirts under collared shirts looks kind of juvenile). When there’s nothing to show but skin, you can leave the second button undone as well.
The almighty tie and its minion, the tie clip
Ties are the easiest way to be overdressed in America, and therefore they are my favorite thing.
- To store your ties, keep them rolled up on a shelf instead of hanging on a hook. We small dandies already have difficulty finding ties that aren’t too long for us. The last thing we need is for them to get stretched even longer while hanging up.
- If your tie is too long for you (the end should not reach past your belt) try a half Windsor knot. It uses up more material than the typical four-in-hand, but its small, symmetrical knot won’t overwhelm your little body the way a full Windsor might.
- If you really just want to use a four-in-hand (maybe you want to look rakish and devil-may-care today) but your tie is too long for you, tie it so that the big part at the front only reaches your belt, and tuck the thin end into your pants. Or, if you are wearing a tie clip, tuck the thin end inside your shirt, between two buttons, and use a tie clip to keep it in place.
- Tie clips are attractive, yes, but they are also functional, and you must remember, form follows function! Their purpose is to hold your tie to your shirt so that it doesn’t flap around. If you’re wearing a sweater or a vest/waistcoat that holds your tie down, a tie clip would be superfluous and make you look silly. (Not the most terrible of sins, but something to keep in mind.)
- The only time you need a tie clip when you’re wearing a sweater or vest is when you want your tie to stand up away from your shirt at the top, like Matthew Crawley on Downton Abbey. This is fabulous, and it also helps keep a long tie from sticking out of the bottom of your vest too much.
Sweaters to keep a dandy warm
Dandies love layers. Skinny dandies like me love layers especially because we have no body fat to protect us in the cold winter months. Sweaters keep us warm, add variety to our outfits, and hide that our shirts are way too big for us because we can’t find anything in our size.
- When acquiring new sweaters, what you like to wear underneath will dictate the type of collar you choose. If you like to wear ties, go with v-necks instead of crewnecks. If you like to wear your tie loose with the top button of your shirt undone, or you just like more of your tie to be visible, go with deep v-necks. Regular v-necks hide most of your tie, but they are excellent for going tie-less.
- To roll up your sleeves while wearing a sweater, push your sweater sleeve up first and then roll your shirt sleeve up, letting the last fold cover the sweater cuff. Don’t roll your sweater sleeve up with your shirt sleeve or you will stretch out your sweater.
- If you were lucky enough to find a sweater that fits you, feel free to wear your shirt untucked so that the tails stick out from under the sweater. If your sweater is too long (it happens to the best of us) then keep your shirt tucked into your pants, unless you enjoy having to adjust it all day.
- When wearing a tie, leave your shirt collar inside your sweater as if your sweater is a suit coat, unless you are being rakish and devil-may-care. When not wearing a tie, pull your shirt collar out of your sweater.
Your lower half
- If your waistband is visible, wear a belt or suspenders. Do I need to tell you not to wear both at the same time? I will anyway. Don’t wear a belt and suspenders at the same time.
- Your belt should vaguely match your shoes – black with black, shades of brown with shades of brown – unless you are wearing a colorful belt or colorful shoes, then anything goes.
- Dark jeans are stylish, but don’t let them hold you back. Pretty much every other type of men’s pants available is more comfortable than jeans; my tightest twill pants are more comfortable than my baggiest jeans ever were. Slim khakis are especially nice.
- If your pants are short enough that your socks are visible when you sit, you’re doing it right. Make sure your socks are up to the challenge!
Everything that goes underneath
- A white or black binder will be visible under a light-colored shirt, so wear an undershirt that is similar in shade to your skin color – not much darker, not much lighter. Pale people like me can wear light heather gray undershirts, for example, whereas darker-skinned people can wear darker gray or brown. White or black undershirts are too much of a contrast with almost everyone’s skin, and this contrast will be visible on your arms and chest where the undershirt ends.
- The same rules apply to white or black bras. Bras come in more colors than binders (unless you buy from Simple Binders), but if you can’t find a bra that’s similar to your skin color, just wear an undershirt to cover it.
- Boxers will usually bunch up and stick out of the waistband of our tight-fitting dandy pants. Briefs or boxer briefs are more comfortable.
- The cardinal rule for socks: colors and patterns, colors and patterns. They need not match the rest of the outfit and they need not match each other, but they must not be boring.
Of course, these are my tips, and you might ignore them with brilliant results. Just remember these wise words, which apply to all people, not just men:
A man should look as if he has bought his clothes with intelligence, put them on with care and then forgotten all about them.
— Sir Hardy Amies, fashion designer