5 Summer Pieces Stylists Still Wear After Labor Day & How to Wear Them

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transitional hero image.jpgE! Illustration/ J. Crew, Abercrombie

There are tons of arbitrary fashion rules, most notably, the myth that you can't wear white after Labor Day. But personal stylist Laura Gregory says it's an outdated rule—and one that she's ready for us all to leave behind.

That means you don't have to put away all of your summer staples. In fact, Gregory says traditional warm weather pieces can serve as the ultimate transitional basics.

Rather than focus on whether a piece is in season or not, focus instead on fabric, proportion and overall styling when it comes to wearing summer styles in the fall.

"Pairing white denim with a white button-up in winter just doesn't work," she says.. "But rather, a monochromatic winter look comprised of a cream satin maxi skirt, oversized cream knit, and matching cream knee high boots looks extra polished and chic in the winter months."

Gregory's hack for transitioning a summer look to something more autumnal? Add one seasonal piece to your look.

"More often than not, adding an intentional third piece like a blazer, jacket or scarf, can completely transform your outfit for the cooler temps."

Below are five of Gregory's must-have summer-to-fall staples plus her expert tips on how to style them.

1. White Jeans

"White denim pairs perfectly with just about any color or pattern," explains Gregory. "Throw on a chocolate brown knit and matching flats or boots. Suddenly, your summer white denim jeans are perfectly paired for Fall. Throw on a tailored suede jacket for cooler days."

PRETTYGARDEN Women's Wide-Leg Jeans

Designed with a hint of stretch for added comfort, these high-waisted wide-leg jeans transition seamlessly into fall, whether you pair them with ballet flats or loafers.

Abercrombie Longline Vegan Suede Jacket

To make white denim feel more autumnal, Gregory suggests throwing "on a tailored suede jacket for cooler days." This longline one is a piece you'll reach for season after season.

Modatope Women's Flats

Complete your look with a pair of trusty ballet flats. This square-toed pick comes in several colors, including a Chanel-inspired beige with a black tip.

2. A White or Cream Satin Skirt

"A white or cream silk/satin skirt is by far one of the chicest items to always grab when you want to look effortlessly chic. Lean into the relaxed minimalism styling and pair with an oversized knit and knee high boots."

Quince 100% Washable Silk Lace Skirt

This smooth silk skirt easily transitions from summer to fall when styled with the right pieces. This one hits below the knee and features a feminine lace trim.

J. Crew 2025 Rollneck Sweater

Pair your smooth silk or satin skirt with a cozy oversized sweater to provide contrast while adding a fall-ready feel. You can't go wrong with this iconic rollneck sweater from J. Crew.

Editor's Pick

Sam Edelman Sylvia Knee High Boot

These knee-high boots instantly add an autumnal touch to your cream satin skirt, whether you opt for suede or leather. You'll reach for this versatile pointed toe pair over and over.

3. A White Crisp Button-Up Shirt

"A white button-up is the perfect staple for year round wear. In the summer months you can layer over a tank open and loose. In the winter, you can layer under a chic knit or tailored blazer. Truly a seasonless staple."

J. Crew Étienne Oversized Button-Up Shirt

Everyone needs a classic white button-up, and this one with a modern oversized fit is ideal for layering.

Cicy Bell Women's Casual Blazer

Available in tons of colors, this chic blazer looks good worn over a tank on hotter days and a button-up on colder days. It has over 23,000 5-star reviews.

4. A Cream Knit Cardigan

"Strategic layering comes into play here," says Gregory, and a "quality cardigan" will add warmth while still looking stylish and polished.

Abercrombie Cable-Knit Crew Cardigan

With its cable-knit design, this slightly cropped cardi looks put together whether it's worn over your shoulder or buttoned all the way up.

5. A Simple Classic Tank

Whether worn beneath a cardigan, a timeless white button-up, or another trendy fall jacket, a well-fitting tank can serve as the base for all your transitional outfit.

Gap Rib Scoop Tank Top

The ideal base for any transitional look, a simple tank can easily take you from summer to fall when paired with a barn jacket, jeans, and cute booties.

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