“Sweater polos have been our signature,” Snyder says. He’s not wrong: If you look at any celebrity in a knit polo in the last few years, they were quite possibly wearing a Todd Snyder knit polo. Unlike tennis-style polo shirts, knit polos are typically more fanciful, with buttons like those you’d find on a dress shirt. Wear it over a tank top in the summer when you’re hanging down at the Wharf, or put it on under a suit for a polished look. “It’s like the dressed-up version of a polo,” Snyder says. If you’re looking for a good option, best to go right to the source and snag one from the man himself. 

Snyder talks a lot about the idea of “grounded and great basics,” and few things are more tried and true than a classic Oxford shirt. Like all menswear, it has peaks and valleys in its popularity — and in our current menswear era, Oxfords are the gateway to sprucing up your weekend outfits. Pair a striped one, like this from Wythe, with a set of shorts and your shoe of choice, and you’ll have an elevated look that’s still effortless in its execution. Pair it with a tie, and it’ll give a dash of prep to your suiting without it reading too frat if you’re looking to keep your consultant coworkers on their toes. 

For Snyder, the versatility of a suit is why he recommends investing in a nice suit that fits and not just something from a fast-fashion spot. “You can wear the jacket as a blazer or with a pair of jeans. You can wear the trousers with a sweater polo,” he says. “You can mix things up.” Something well-fitting and stylish, like this suit from Drake’s, will do the trick next time you want to dress up for your Le Dip resy — but you’ll have to get the pants and jacket separately.

While it’s way too early to think about wearing an overcoat, now’s actually a good time to start considering what coat you’ll want for that cold weather. “One of my favorite things to do is pairing overcoats on their own, with sweatpants or with jeans,” he says. “The overcoat has become the go-to piece for men that are a little more casual on the weekends but then also the guy who’s going to work and needs something to throw over his suit.” Look for options in versatile colors like navy, black or gray. This super swanky one from Canali is an investment, but exactly the cut and style of what to wear now. You want your overcoat to feel like a cape — slightly drapey but not overly so. Putting it on should make you feel like a superhero while keeping you warm as you run to get a coffee at Baked & Wired this winter on your lunch break. 

“Nothing beats Alden,” Snyder says when it comes to footwear. “That’s usually my go-to piece. I usually wear it with a trouser, but I also wear it with jeans. I always like mixing that up.” The New England shoemaker started all the way back in 1884, continuing to produce exceptional footwear in the intervening 120 years(!). We specifically recommend these suede penny loafers, as the style is decidedly of the moment right now and can easily be spruced up with dressier trousers like Snyder mentioned, or with a pair of jeans or shorts if you’re feeling adventurous. The suede is buttery smooth and will go with anything and everything in your existing wardrobe. If dress shoes aren’t your bag, Todd also recommends a pair of classic, white sneakers, like the beloved Adidas Stan Smiths, especially if you’re going to spend a weekend walking around Union Market.