How to Dress for Every Day of the Week
If there was an upside to the Don Draper era of menswear, it’s that you didn’t have to think much about what you wore. Gray or navy suit, white shirt, tie, and wingtips during the week; chinos and an Oxford during the weekend.
The downside, of course, was that until you retired and moved to Florida—where you could swap your suit for pastel-colored pants and some fancy white shoes—you were basically stuck in a clothing rut, day-in, day-out.
Today, a much more relaxed attitude about office dress codes means there's more freedom to have fun with your wardrobe. Unfortunately, with that freedom comes the burden of choice—and a higher risk of messing it up. We're here to help with seven outfit ideas that'll get you through the entire week—and guarantee you're the most stylish guy in the room, no matter where you are.
Blazer by Boss, pants by Boss, shirt by Boss, shoes by Boss, tie by Brunello Cucinelli.
Now that more offices err on the side of business casual, the suit as a work uniform has largely gone the way of the dodo. But that doesn’t mean you still won’t occasionally need one, whether it’s for a meeting with the bosses or lunch with a new client. On those days, keeps things classic with a slim-fit navy suit, a crisp white cotton dress shirt, a pair of black leather Derbies, and a subtly stylish tie.
Blazer by Boss, pants by Boss, T-shirt by Sunspel, sneakers by Common Projects.
The beauty of a suit is that it can be dressed up or down depending on the occasion. For a more casual but still right for the office approach, simply pair it with a solid T-shirt rather than a shirt and tie, and sleek minimalist sneakers instead of dress shoes. It’s a look that isn’t overdressed, but will elevate you above your chinos-and-a-button-down-wearing coworkers.
Blazer by Etro, shirt by Gitman Bros. Vintage, jeans by Levi's, boots by Mr. P.
Jeans aren't just for casual Friday. Mix a dark pair with a crisp white Oxford shirt and a navy or patterned blazer for a look that's totally appropriate for mid-week. Add a shoe that’s either a little more adventurous (like minimalist sneakers or Chelsea boots) or a little more conservative (like suede lace-up boots), depending on your preference and what the office dress code dictates.
Sweater by Saint Laurent, jacket by Boss, pants by Prada, shoes by Church’s.
Clean and simple is always a good approach for office attire. Dialing things down and focusing on fit and quality will guarantee that you look good without ever coming off as overcooked—especially toward the end of the week when things are (hopefully) starting to mellow out. The best way to do this is by pairing a lightweight cashmere or merino crewneck sweater with trousers and a pair of leather Derbies. Throw a bomber over it when you leave the office for a little added edge.
Blazer by Boglioli, sweatshirt by Boss, jeans by Boss, sneakers by Converse.
Office dress codes may have gotten more relaxed, but that doesn’t mean you should approach Casual Friday as Even More Casual Friday (important note: Sweatpants are never okay for the office). Think of your Friday outfit as a softer version of your everyday look. Rather than dark jeans, try denim with a bit of a fade. And instead of a crewneck sweater, try a (nice) crewneck sweatshirt with a blazer on top.
T-shirt by Bianca Chandon, jacket by Boss, shirt-jacket by Filson, pants by Acne Studios, shoes by Clark’s.
Saturday should be about maximizing comfort without sacrificing style, whether you’re headed out to brunch or simply bumming around town. If it’s a brisk day out, that means layers: Start with a bright T-shirt for a pop of color, then add a zip-up hoodie and, if you need more, a shirt-jacket over that. Finish it off with a pair of slouchy cotton trousers and, rather than sneakers, mix things up with some very on-trend and ultra comfy Clark’s Wallabees.
Pants by Boss, hoodie by Stone Island, sneakers by Nike.
After a long week (and hopefully, a fun and adventurous first half of the weekend), Sunday is where you can truly unwind. That’s right: It’s finally time for sweats. However, just because you’re making comfort your primary goal doesn’t mean you have to look sloppy. Opt for a pair of stylish track pants (rather than those grungy sweats you’ve had since college), a hoodie that isn't just black or gray, and your most stunt-worthy pair of sneakers.
This story originally appeared on Esquire.com. Minor edits have been made by the Esquiremag.ph editors.