Help Me Dress Myself: Looking Smart While Freezing Your Butt Off

How to dress for work—or a job interview—when it’s really, really cold outside.


Are you one of those guys who wants to look stylish but finds it doesn’t come all that naturally? We feel you. Don’t fret: With some advice from Jessica Chance, men’s stylist at Rag & Bone and menswear blogger, we’re all going to learn how to dress a little better. In this edition, we’ll be looking at how to dress for work—or a job interview—when it’s really, really cold outside.

Step #1: Learn to Layer

Rather than showing up to work dressed like you’re ready to climb Everest, Chance suggests layering your clothes. “Because we’re talking work attire, chances are you’re already layering—you’ve got a button-down, topped with a blazer and possibly finished off with a peacoat. If it’s extra cold out, feel free to add an extra layer of long underwear or Under Armour underneath your shirt.” That’s sure to keep you nice and toasty without having to wear anything too puffy.

Step #2: Wear Sturdy Shoes and Socks

When it comes to snowy weather, Chance says you have two options for footwear when it comes to a more formal look: “(1) Either wear a snow boot on the way to the office, and then change into a more formal shoe when you get there, or (2) wear your standard formal leather shoes and hope for the best—just make sure they have good grips on the bottoms so you don’t slip on ice.” She also suggests wearing a thick pair of wool socks if you’re going the boot route for that extra dryness and warmth needed in wet, winter weather.

Step #3: Know Your Headwear Options

“Wearing a beanie with a suit is a sort of clash of informal and formal, so I’d recommend some kind of wool hat, like a cap or a fedora,” Chance says. “Just make sure it matches your suit or your peacoat to keep your outfit looking clean and put together.” If it’s so cold that you absolutely must wear a beanie, however, Chance says that’s okay as long as you take it off as soon as you set foot in the office.

Step #4: Wear a Scarf

If the wind is blasting down the neck of your flimsy suit, you should consider a scarf, but Chance suggests keeping it minimal: “Avoid bright colors—navy blue and black are good—as well as crazy patterns and wild tassels hanging off the end.” She also recommends wrapping it around just one time, or letting it sit underneath your coat rather than getting crazy with it. If you want to know how not to wear your scarf, take a look at Lenny Kravitz and do less.

Step #5: Invest in a Pair of Gloves

“Black leather gloves are not only a great way to stay warm, they also go really well with suits,” Chance explains. “Generally speaking, leather is your best bet when you’re dressing more formal in cold weather, because it’s not cheap-looking like most puffy winter clothes.” Feeling like a secret agent is just an added bonus.

If you have any questions about getting the look you want—fits, cuts, colors or anything else fashion-related—email us at We’ll have Jessica answer it in an upcoming post.