A windbreaker used to have a very specific job: keep the wind off you.

You wore one for a morning walk, a tennis match, a hike, or when the weather suddenly changed. It wasn’t usually the piece you thought about when putting together an outfit.

That part has changed.

Look at what celebrities are doing with them. Hailey Bieber has worn a cropped Miu Miu windbreaker with capri pants and kitten-heel flip-flops. Kendall Jenner has paired a bright windbreaker with relaxed jeans and simple sneakers. Gigi Hadid has mixed hers with trousers and boots. And Rihanna has taken the idea much further, wearing sporty outerwear with pieces that have almost nothing to do with athletic dressing.

What I like about these outfits isn’t that they’re celebrity looks we need to copy.

It’s that they give us ideas.

The windbreaker doesn’t have to turn the entire outfit into sportswear. In fact, it can be more interesting when everything around it goes in a different direction.

Hailey Bieber: The Sporty Jacket Meets the Feminine Shoe

One of Hailey Bieber’s windbreaker outfits is a particularly good example: a cropped gray-and-navy Miu Miu jacket with capri pants and kitten-heel flip-flops.

At first, those pieces don’t sound like they belong together.

That’s exactly why they work.

The jacket brings the casual, sporty element. The shorter pants keep the outfit light, while the little heels introduce something delicate.

Try the idea yourself

You don’t need a designer windbreaker or kitten heels.

Try:

Cropped windbreaker + capri pants + ballet flats

or

Oversized windbreaker + straight jeans + low heels

or

Windbreaker + midi skirt + delicate flats

The important part is the contrast. If the jacket is sporty, let the shoes or bottom bring something different.

Kendall Jenner: Let the Jacket Supply the Color

Kendall Jenner has shown another easy way to wear the trend: make the windbreaker the strongest color in an otherwise simple outfit.

A bright yellow version with loose gray jeans and white sneakers is a good example.

This is a very useful idea if you aren’t someone who wants a closet full of colorful clothes.

You don’t need colorful pants, shoes, bag, and accessories.

One colorful jacket is enough.

Try the idea yourself

Choose a red, cobalt blue, yellow, or pink windbreaker.

Then wear it with:

• Blue jeans and a white T-shirt
• Cream trousers and a simple tank
• Black jeans and a gray sweater
• White jeans and a striped shirt

The jacket becomes the thing people notice first, while everything else gives it some breathing room.

Gigi Hadid: Put It With Something Unexpected

Gigi Hadid has worn windbreakers with pieces such as plaid trousers and boots—exactly the sort of combination that makes the jacket feel less like activewear.

This is an idea worth borrowing.

If you always wear your windbreaker with leggings and sneakers, try changing just one part.

Keep the jacket and replace the leggings with trousers.

Or keep the sneakers but wear a skirt.

Or keep the jeans but switch the sneakers for boots.

You don’t have to reinvent the outfit.

Why it works

The windbreaker has a relaxed shape and often a technical fabric. A trouser with a different texture or structure gives the outfit another dimension.

That’s what makes the combination feel considered rather than like you simply grabbed the nearest jacket.

Rihanna: Don’t Be Afraid of the Completely Unexpected

Rihanna has been taking sporty outerwear into much more dramatic territory for years.

One memorable example paired an electric-blue Martine Rose windbreaker with a miniskirt, fur stole, and strappy stilettos.

You probably aren’t going to wear that exact combination to pick up groceries—and you don’t have to.

The useful idea is much simpler:

Put something feminine next to something sporty.

Try a windbreaker with a satin skirt.

Or a short skirt and boots.

Or wide-leg trousers with a fitted top.

The jacket doesn’t need to match the mood of everything else.

It can be the interruption.

Jennifer Lawrence: Neutrals Don’t Have to Mean Boring

Jennifer Lawrence recently stepped out in a camel windbreaker with red track pants, brown boat shoes, and a black baseball cap.

There are several good ideas here.

First, the camel jacket isn’t the obvious black or navy choice.

Second, the red pants add color.

And third, the boat shoes take the outfit somewhere different from the usual sneaker-and-windbreaker combination.

Try the formula

If you have a camel, tan, or beige windbreaker, try it with:

Red trousers + brown shoes

Blue jeans + burgundy accessories

Cream pants + navy top

Chocolate brown pants + white T-shirt

A neutral jacket gives you plenty of room to play with color underneath.

Zendaya: Sometimes Matching Actually Works

Not every celebrity look needs to break the rules.

Zendaya has also been seen wearing the windbreaker in a more traditional sporty combination, with matching athletic pieces and sneakers.

And there is something to be said for that approach.

If the jacket has a strong shape or interesting color, matching pants can make the outfit look deliberate rather than random.

When should you match?

A matching set works particularly well when:

• The colors are strong but simple
• The jacket and pants have similar proportions
• You keep the accessories minimal
• You want the outfit to look sporty rather than mixed

For everyday wear, break up the set with a different T-shirt, handbag, or shoes.

That gives you another outfit without buying another jacket.

Hailey Bieber’s Miu Miu Moment Also Says Something Else

Hailey’s windbreaker wasn’t simply a practical jacket. Miu Miu had already placed the idea on the runway, and Bieber’s street-style appearance showed how easily the concept could move into everyday dressing.

More recently, Miu Miu’s Fall/Winter 2026 campaign with Bieber also features a two-tone windbreaker with technical trousers, showing that the brand continues to play with this sporty vocabulary.

You don’t need the Miu Miu version to get the idea.

Look for the details:

Two-tone color

Cropped shape

Drawstring or elastic details

Lightweight fabric

A slightly roomy fit

Those details can make a basic windbreaker much more interesting.

How to Choose Your Windbreaker Color

Color will determine how often you reach for it.

Navy

The easy choice if you want something that works with almost everything.

Try it with cream, white, denim, gray, tan, and red.

Olive

Especially good for fall.

It works naturally with denim, brown, cream, black, and camel.

Camel

A little unexpected for a sporty jacket and particularly nice with denim and red.

Cream

Great if you already wear lots of neutrals.

Try cream with ivory for a tonal look, or break it up with denim or chocolate brown.

Red

If you want the jacket to be the outfit.

Wear it with jeans, black trousers, cream pants, or even a simple gray skirt.

Cobalt or Bright Blue

This is the choice for someone who wants color without going into neon territory.

It looks especially good with white, cream, gray, black, and denim.

Pink

A softer way to experiment with color.

Pale pink works nicely with gray, cream, white, and faded denim.

How to Wear a Windbreaker Without Looking Like You’re Going to the Gym

This is where the styling becomes important.

Don’t automatically pair it with another sporty piece.

Instead, try one of these combinations:

Windbreaker + wide-leg trousers + loafers

The trousers change the direction of the jacket.

Windbreaker + satin skirt + ballet flats

The skirt gives the lightweight jacket a completely different setting.

Windbreaker + jeans + ankle boots

Simple, but more autumn-ready than sneakers.

Windbreaker + dress + sneakers

A great way to make a dress work for daytime.

Windbreaker + tailored shorts + loafers

Good for warmer transitional weather.

Windbreaker + capri pants + low heels

A nod to Hailey Bieber’s approach without copying her outfit.

The Shoes Are More Important Than You Think

If you want to experiment with your windbreaker without buying anything else, start with your shoes.

Sneakers keep the original sporty feeling.

Loafers give it a preppy direction.

Ballet flats make the outfit softer.

Boat shoes create that relaxed American sportswear feeling seen in Jennifer Lawrence’s recent look.

Ankle boots make it work beautifully for fall.

Kitten heels or low heels create the biggest contrast.

The same windbreaker can look completely different depending on what you put underneath it and what you wear on your feet.

What About Accessories?

This is another place where you can change the personality of the outfit.

Try a baseball cap for a more casual look.

A structured handbag pulls the outfit away from traditional sportswear.

Gold hoops can add a little shine.

A silk scarf can make a simple windbreaker-and-jeans combination feel more personal.

And sunglasses are almost always a good idea with this type of outfit.

You don’t need all of them at once.

Pick one.

The Windbreaker Is Particularly Good for Travel

There is a practical reason I think this trend makes sense beyond celebrity street style.

Windbreakers are light.

They don’t take much room in a suitcase.

They work over T-shirts, sweaters, dresses, and activewear.

And they are useful when the weather changes during the day.

For a travel wardrobe, I’d choose a neutral one—navy, olive, camel, black, cream—or, if the rest of your clothes are mostly neutral, one strong color.

Then wear it with jeans one day and trousers or a dress the next.

That is how one jacket earns its suitcase space.

Six Celebrity Ideas to Take Into Your Own Closet

You don’t need to dress like a celebrity to borrow the idea.

Hailey Bieber:
Sporty windbreaker + feminine shoes.
Why it works: the shoes change the direction of the jacket.

Kendall Jenner:
Bright windbreaker + simple jeans + sneakers.
Why it works: one strong color gives a basic outfit some energy.

Gigi Hadid:
Windbreaker + trousers + boots.
Why it works: the trouser-and-boot combination takes the jacket away from the gym.

Rihanna:
Windbreaker + feminine or unexpected pieces.
Why it works: the contrast is the whole outfit.

Jennifer Lawrence:
Camel windbreaker + colorful trousers + unexpected shoes.
Why it works: the neutral jacket makes room for color and texture.

Zendaya:
Matching windbreaker + pants + sneakers.
Why it works: sometimes committing to one idea looks better than mixing too many.

The One Piece to Take From All of This

You don’t have to decide whether your windbreaker is a sporty jacket or a fashion jacket.

It can be both.

Wear it with leggings when you’re actually being active.

Wear it with jeans when you’re running errands.

Put it over a dress when you want something unexpected.

Try it with trousers when you want to change the mood.

And if you find a color you really love, let the jacket be the thing that brings the outfit to life.

That’s probably the most useful thing about the windbreaker: it doesn’t require you to change your wardrobe. It gives the clothes you already own another combination to play with.