Help Me Dress Myself: Upgrading the Hoodie

A stylist explains how to look like you made an effort, even though you’re still comfortably swathed in a hoodie.


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, menswear blogger and men’s stylist at Rag & Bone, we’re all going to learn how to dress a little better. In this edition, we’ll be looking at how to transform a hoodie from hangover attire to something a little cooler.

Step #1: Keep it Simple

Rather than sporting a hoodie that has your favorite band’s logo spread across the front, Chance recommends keeping graphics to a minimum. “You can never go wrong with a plain Nike hoodie, even if it has a small swoosh on it,” she says. “Just make sure to pick a versatile color like black, grey or white.” And if sportswear isn’t your style, any plain black, grey or white hoodie will look just fine.

Step #2: Layer It

Chance says the coolest way to wear a hoodie is to layer it underneath something else, whether that be a leather jacket, a denim jacket or a winter coat. She does, however, warn that wearing a flannel over a hoodie died (or should have died) along with grunge: “That would be a bit of an outdated look nowadays,” she says.

Step #3: Make a Casual or Athletic Outfit out of It

Once you have your hoodie picked out, Chance says you have two options when putting together an outfit: Keeping it casual or going full-blown athletic. “If you’re going for a more casual, day-to-day look, you want to wear your hoodie with a pair of dark, fitted jeans—preferably black,” she explains. “And if you’re going for more of a relaxed, athletic look [like athleisure], wear your hoodie with a pair of black joggers.” No matter which route you decide to take, Chance suggests finishing off the outfit with a simple pair of black or white sneakers.

Step #4: Know Your Other Options

If the standard pullover hoodie isn’t working for you, Chance suggests opting for one with a zipper. “Zip hoodies are nice because you can leave the front open,” she says. “That way, when you go to layer it, all anyone will see is the hood. You get the comfort of the hoodie, with the straight up look of a leather jacket or whatever else you decide to layer over it.” And if you want to ditch the hood altogether, Chance says a basic crewneck pullover also has that casual and comfortable vibe that comes with wearing a hoodie. Either way, go forth and prove to the world that comfort does not have to be sacrificed for fashion.

If you have any questions about getting the look you want—fits, cuts, colors or anything else fashion-related—leave it in the comments and we’ll have a stylist answer it in an upcoming post.