Going from a casual day at the office to a dressed-up date in the evening doesn’t have to mean a complete outfit overhaul. If you know what to change, a little sartorial tweak here or there can almost completely transform an ensemble, giving you much more flexibility over your day’s dress code.
The trick is to identify the key items to keep on hand, and know how and when to apply them. Execute well, and you’ll look extra sharp for whatever you’ve got in store for the evening.
Change into a Pair of Lace-Ups
It’s often said that a man’s shoes can be make or break his outfit. Don’t believe it? Go put on a pair of slim-fitting jeans and a relaxed button down with a pair of sneakers. Then swap the sneakers out for a pair of polished lace-ups and see for yourself how drastically the vibe of your outfit changes.
The specific style doesn’t matter so much – wingtip, blucher, oxford, derby – so long as they look like something you’d wear with a suit. A dark, understated pair will go with most any outfit, from classic indigo denim to military-inspired khakis. Though under no circumstances should your lace-ups have square toes – that was wrong in the ‘90s, and it’s still wrong today.
So when you’ve got a big night planned, think ahead by stashing a pair of these in your bag. Then leave your everyday office kicks behind once you clock out, and put your best foot forward. And if you want to go bold, cuff the ankle of your pants to draw eyes downwards towards your impeccably polished shoes. You’ll go from casual to confident in seconds.
Button Up an Oxford Shirt
Wear or bring one of these on any day you might have an occasion to get dressy.
The beauty of oxfords is that they can spruce up almost any outfit, from jeans to shorts to chinos to wool trousers and anything in between. The heavy, plain weave cloth makes it informal enough to wear with casual stuff, but the clean button-down design makes it sharp enough to wear with formal stuff. Untucked and/or unbuttoned with the sleeves rolled up, it's perfectly casual. Tuck it in and button the cuffs, though, and you'll instantly cross over into put-together territory.
Your crush just enthusiastically agreed to grab a cocktail after work, but today was the day you wore your vintage Empire Strikes Back tee? No problemo. Toss on your oxford and you're good to go.
If you want to be extra prepared, you could keep one ironed and ready in a drawer at work, Don Draper-style. It'll come in handy in case you spill coffee on yourself before a big meeting, spend the night at someone else's place, or need a last-minute way to improve your outfit before leaving work. It may seem like a bit much – unless you're accident-prone or have a very dynamic social life, you may never need the spare – but in last minute wardrobe emergencies, it’ll be a lifesaver.
Find the Right Fit
It may seem obvious, but you want yours to be slim but not tight, just like almost any other piece of clothing. That'll give any physique a structured, streamlined look. You shouldn't have much (if any) extra fabric around your torso or arms, but you should also be able to move freely.
Ditch the Undershirt
If you’re wearing the collar open, a t-shirt peaking up above the neckline can derail the uniform cohesion of an oxford in an instant. Wear a deep v-neck that's not visible when your collar is open, or nothing at all.
Add a Tie...
A slim tie can work wonders with even the most casual collared shirts (excluding polos – we hope that's obvious). A solid navy one is especially versatile, if you want to keep one in your desk as per the points above. It takes up almost no room, and when your boss' boss calls a last minute meeting, you’ll be prepared.
Whatever kind you choose, tie it onto most any shirt that's not too wrinkled. Denim, chambray, flannel, gingham, plaid… all fair game so long as they're tucked in, with a collar that's sturdy enough to lie flat and one chest pocket, max.
Finish with a Tie Bar
This is optional, but a simple and sleek tie bar positioned between the third and fourth shirt button makes any outfit sing, whether you’re finishing it with a suit jacket, an M-65 jacket, or anything in between. It may seem like the most obvious tip possible, but keeping a tie in your draw at work is always a good idea –
…Or a Pocket Square
This is perhaps the simplest way to show that you put some thought into your getup.
A crisp, white square will work, but try going a little bolder with unique patterns or cloths if you're feeling especially stylish. Or just use a bandana – it's a clever way to bring a workwear edge to the dressed-up look. And while they're mostly seen on blazers, there’s no reason why you can’t pair one with your jean jacket or overcoat.
And don’t worry too much about how neatly folded the square is. You're aiming for rakish nonchalance, not teachers-pet perfection.
After you're classed up, all you've got to worry about is the hard part: impressing whoever you dressed up for, beyond the sartorial first impression. And for that, we're sorry to say, you're on your own.
