6 Windbreaker Looks to Blow Your Hair Back

How to Wear a Windbreaker
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Last Updated on December 2, 2022

It’s been breaking wind since before you can remember and it’s still the hottest way to fight the chill factor. The windbreaker reached iconic status in the nineties and has never looked back since. Every kid who was anyone, owned one. Hell Yeah, you did! And with good reason too.

The windbreaker was the answer to every mom’s biggest fears wrapped up in one functional item. In fact, in my opinion, it was this collective maternal consciousness that turned one designer’s predilection for Bauhaus into a major fashion trend.

With Game Boy in hand and Super Mario on your mind, chances are you were happily unaware that you looked like a walking traffic sign in your color blocked breaker. Even more reason for mom to be able to find you in a crowd. And it worked for husband’s too. These days, you’re more likely to find the windbreaker of your dreams in the back of your dad’s closet than at your local thrift store. The vintage windbreaker has become a hot ticket item.

While the windbreakers of the nineties were almost always loud and proud, the uber functionality of this item has spawned iterations of every ilk. The beige bland child of this nineties legend now stands firmly in the realm of Normcore. But then again, one could argue the very roots of Normcore lie in the flannel shirts and “slacker” anti-fashion style of Grunge which reached its high in ’93/94.


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And yes, sure, the windbreaker is an easy item to style. Especially if your go-to look is Friends inspired and Normcore is your middle name.

The windbreaker with jeans and sneakers is a classic and stands the test of time. And the windbreaker pretty much does the work of your trusty, if somewhat tired old sweater adding vintage appeal to your everyday-cute outfit. Go head-to-tonal for an easy fix style solution and have your white windbreaker outfit, your black windbreaker outfit, your red windbreaker outfit, your blue, yellow and pink and every other colour of the rainbow windbreaker outfit, and you’re sorted for days.

And to make things “easier”, the nineties is back in a big way. Key millennial must-haves like bucket hats, bootleg pants and crop tops are currently filling the rails of your local clothing chains so you don’t have to go digging through piles of pre-loved frippery to find fashion friends to wear with your favourite vintage vestment.

But be warned if you don’t consider yourself an everyday, regular normal MF with a singular style that stands you out from the crowd. Unless you aspire to the aesthetic of that “Buffy the Vampire Slayer” mom who hasn’t taken off her black stretch choker since ’98 (you know that one lurking in every school parking lot) you’re going to need to apply some sartorial savvy when crafting killer Y2K looks that don’t look like they’ve been through the Decade Warp dryer.

On the positive side, the nineties was nothing if not inclusive. A trend that has snowballed and encouraged the levels of body positivity and freedom of personal expression that we enjoy today. So whether you’re a Rave-Girl, Posh, Scary or Sporty Spice, or a Baby Girl lover of all things nice, we have the windbreaker look for you.

#1. Hippie Chicster

90s Hippy Chicster Outfit Ideas

| Pink Sunglasses | Flower Bucket Hat | Butterfly Wing Earrings | Rainbow Bag | Floral Windbreaker | Bootleg Jeans | Striped Top | Pastel Trainers | Logo Print Bucket Hat | Green Crop Top | Two Strap Sandal | Ochre Windbreaker | Multi Color Windbreaker | Yin Yang Shoulder Bag | Lilac Sunglasses | Butterfly Necklace |

Head to toe boho babe looks are so last century. Serve a sporty slant to your Y2K hippie style and pull that girl right into the 21st century. Nothing adds an athletic edge like a windbreaker, and while pretty floral prints look right at home here, the nineties color block aesthetic brings an attitude and a much needed sense of urgency to the call for Peace.

The elements are all there: Head in the clouds bucket hats, butterflies, flowers, rainbow hues and rose tinted shades. And Birks to keep your feet firmly on the ground. Earthy tones of brown and ochre softened with pretty pastels or popped with hot pink or grassy green. This mash up of seemingly opposing sartorial styles speaks volumes about the prevailing need for Peace, Love and Understanding in our world today.

Check Out: 90s Sunglasses: Keeping the stars in the sun

#2. Nineties Normcore

90s Normcore Windbreaker Outfit Ideas with bucket hats and doc martens

| Color Block Windbreaker | Check Bag | Faux Fur Bucket Hats | Knit Mini Dress | Ankle Boots | Printed Tee |

Cargo Pants | Brown & White Windbreaker | Zebra Print Trainers | Grey & White Bucket Hat | White Knit Dress | Camo Print Windbreaker | Lace Up Boots |

If you’re more Avril Lavigne than Jessica Simpson, you probably remember the nineties for the grungy tomboy looks that paved the way for the Normcore trend of today. Unisex items, clean lines and uber practicality drive this “so over fashion” style that has adopted many of the staple items of the nineties. Flannel shirts, beanies, cargo pants and of course, the windbreaker, form a big part of this look.

Outdoor brands like The North Face and New Balance have been elevated to a level of fashion ability never before appreciated by the sartorial set and this “trend” looks to continue into the future. With so many other pressing issues, health, environmental and more recently world peace, a simple, functional approach to fashion just makes sense. The nineties never looked so minimal, or so right.

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#3. Rave Rebel

Rave Rebel Outfit Ideas with Windbreaker

| Metallic Windbreakers | Bucket Hats | Printed Crop Top | Black Leather Pant | Silver Windbreaker |

Check Skirt | Tech Fabric Cross Body Bag | Tie Dye T-Shirt | Platform Boot | White Logo Printed T-Shirt |

Check Pants | Pink Op Art Top | Pink Sunglasses |

It may or may not be true that “It’s over, nobody listens to techno” but it’s fair to say that the clothing never got a bad rap. This year sees the return of Nineties Rave Girl looks, trippy op art prints, shiny technical fabrications, and clean body con lines to pull some millennial moves in.

And if the club scene is not for you, you can always sport your cyber side on your morning run because this streamlined style just works, however you choose to move your body.

The usual suspects are there: Bucket hats, bare midriffs, built up boots and byte sized bottoms. But the windbreaker in this case, is anything but bland. Shiny finishes, happy shades of neon and flashes of fluorescence turn any ol’ plain breaker Jane into queen of the club.

#4. K-Pop Princess

Nineties K Pop Outfits: Windbreaker, satin dress and converse plus much more

| Bucket Hat | Blue Slip Dress | Platform Sandals | Pastel Windbreaker | Pleated Skirt | Pink Bag |

Stripe Sport Socks | Canvas Sneakers | Pink Slip Dress | Color Block Windbreaker |

The lingerie inspired slip, the ubiquitous dress of the nineties, is back in a big way. Whether you choose to layer it over a tee for day or go bare shouldered by night, this is arguably the prettiest nineties babe look by far. Made famous by Kate and crew, this dress screams super model. But if you’re more street than sleek, pick a look from Courtney Love’s book and mix the girly with some gnarly. Yes, I did just use that word! This is a nineties blog after all.

Seriously though, nasty girls wear this dress best and dressing it down just ups the allure. Black chunky soled shoes (the only nineties footwear option) sport socks, a baby tee, and a bucket hat-all de rigueur nineties must haves. Ditch the twee cardigan and top this classic slip with a color block windbreaker-the 21st century version of the grungy flannel shirt. This sport inspired cover up takes your pretty in pastel K-Pop Princess look to a new level of Courtney inspired cool.

However you choose to wear your windbreaker, whether you go for new or vintage, this nineties baby still rocks its socks thirty years on.

This versatile and functional item has found its place on the A-List and the O-List alike, and everywhere in between. its sporty heritage ensures its credibility on every 21st century street and it’s still the coolest way to give new life to the looks of the decade of the day: Y2K all the way, wind break your style in a big way.

Bonus Outfits

#5. Street Cool

A great transitional piece that is easy to wear all year round. It matches all your looks, as it goes perfectly well with either white Reebok sneakers or chunky combat boots.

  • For winter, take Kaia Gerber’s advice and be safe in an all-black ensemble. Pair black jeans with a black turtleneck, using the shell coat as the accent, and you’ll stay warm and stylish. 
  • For in-between seasons, opt for the casual 90s classic by combining the infallible white t-shirt or tank top with your denim jean of preference — a recently revisited combo by Malila Obama in New York.
  • For summer outfits show your legs throwing it over lightweight dresses, or wear it as a zipped up shirt with shorts, skirts or pants. If it gets really hot and you love your windbreaker, wear it as a dress and tie a belt around your waist, see how Hailey Baldwin made it work — hats off for the creative and minimal approach.

#6. Bold Way

Surprisingly, this sports garment can also compliment your look when attending fine events. Over the years, different stars have made outerwear-coordinated appearances, as designer and mainstream brands made it available in a multitude of styles, colors, and print variations.

  • All things matching, in 2017. The color block three-piece by Versace. Check how glamorously Lady Gaga looked at the Super Bowl press conference, and stepped up the game, by accessorizing it with black sandals.
  • Silver works, in 2018. Beyoncé kept everything shiny, windbreaker, bodysuit, and thigh-high boots, during her On the Run II tour.
  • Smart and minimal, in 2019. Kim Kardashian wore a Northface windbreaker as a shirt, black leggings as bottoms and high-heeled ankle boots with accordingly neat and sleek hair.