How to Wear a Windbreaker

dream maker, breeze taker

By Gabi Meyers | Last Updated: Jun 23 2022 | 3 min read

Guys, I feel like I have pushed more jackets and layers than any other category of 5 Days, 5 Ways. And yet somehow, I still think there is room for (at least one) more.

Outerwear is the first part of your outfit that most people see, so it’s definitely worth more consideration than say, your socks (I think fun socks are still important just slightly less so). I’m not saying every jacket you own has to be a sick leather bomber, but I am saying it’s worth upgrading even the most casual jackets in your wardrobe, because you should only give yourself the option to look good, even if you’re just grabbing coffee.

Enter, the windbreaker. If you don’t already have one, opt for a slim fit throughout so you can layer it over or under throughout the year. A vintage style racing stripe or color-block are highly encouraged.

Lightweight and durable, a windbreaker can be an easy layer to add even in the hottest months.

How to wear a windbreaker in a stylish way:

MONDAY

windbreaker, tracksmith, rag&bone, jack spade, bonobos, nn07, maximum henry

Blazer: Suit Supply, $499 | Shirt: NN07, $50 | Chinos: Bonobos, $88

Shoes: Rag & Bone, $315 | Belt: Maximum Henry, $115 | Bag: Jack Spade, $298

Wear it well: Layer your windbreaker under your blazer for an athleisure look that’s work appropriate.

TUESDAY

windbreaker, neighborhood, shuttle notes, obey, ray-ban, vans, united by blue

henley: Shuttle Notes, $75 | shorts: Neighborhood, $144 | sneakers: Vans, $50

socks: Obey, $11 | sunglasses: Ray-Ban, $150 | water bottle: United By Blue, $28

Wear it well: Channel your favorite camp counselor look with a windbreaker over some shorts and a henley for those chilly summer mornings.

WEDNESDAY

tracksmith, windbreaker, saturdays nyc, monocle, todd snyder, allsaints

shirt: Saturdays NYC, $160 | trousers: Todd Snyder, $228

shoes: George Brown BILT, $295 | fragrance: COMME des GARÇONS x Monocle, $95

Wear it well: Bring your windbreaker to date night, just in case it gets chilly.

THURSDAY

windbreaker, tracksmith, timex, bonobos, the graduate, ben braddock, vejas, lacoste

polo: Lacoste, $98 | chinos: J.Crew, $68 | sneakers: Veja, $115 | watch: Timex, $55

Wear it well: Go for a vintage vibe by pairing your windbreaker with a classic polo shirt and white tennis sneakers.

FRIDAY

windbreaker, etudes, aviator nation, warby parker, aesop, air jordans, nike, denim refresh, tracksmith

tee: Aviator Nation, $75 | jeans: Etudes, $126 | sneakers: Nike, $140

Wear it well: If you want your shoes shine, the basic design of a windbreaker will keep all eyes on your feet.

Gabi