How To Wear Your Favorite Summer Staples In The Fall

Double the fun.

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white tank with baggy jeans
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From a styling perspective, the shift from August to September is a study in contrast. Bikinis are traded in for blazers as everyone’s wardrobes transition to crisp autumn weather. It can, of course, be a bit sad bidding adieu to the carefree days of beach season, but there’s something undeniably magical about that post-Labor Day ‘back to school’ feeling. And while you’ve still got a month and a half before this seasonal swap occurs, it’s not a bad idea to start planning how to wear your favorite summer clothes in the fall — most of them fare better in cool temperatures than you’d think. The key? “Layer, layer, layer!,” t.a. Founder Telsha Anderson-Boone says. “The best piece of clothing is one that can be worn year round by adding or subtracting something as simple as a sweater.”

Doubling down on this sentiment, J.Crew Head of Women’s and Kids Design Olympia Gayot notes she wants her wardrobe to work hard for her. “I’m not bothered by wearing the same thing different ways across multiple seasons,” she says. “The more you wear something is a testament to how great it is.” Gayot also brings up an important point about clothing hues. “Color is something that can also be worn year round,” she explains. “Just because the weather changes doesn’t mean your wardrobe has to become subdued. I often go for full color looks, monochromatic head-to-toe shades, or I mix neutrals with color.” she says, citing a few of her favorite combinations to keep in the mix. “I love camel or cream as a base for brights like orange and yellow in fall, or navy as a base for shades of green and other bright blues.”

Courtesy of Cory Sargeant

Another styling tip Gayot relies on is layering shades of the same color in different textures. “Mixing [materials such as] cashmere, chino, denim, silk, wool, suede, leather, all in the same color family can look really sophisticated and dimensional,” she explains. All of which is to say: It doesn’t really matter if you are wearing something light and wispy when the temperatures drop so long as you’ve got enough cozy fabric to anchor it.

Ahead, TZR tapped industry experts to share more of their tried-and-true tips for keeping summer essentials on rotation in the cooler months — and, of course, the transitional pieces you shouldn’t pack up quite yet.

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The Slip Dress

A ‘90s staple that’s held its own for the last several decades, the slip dress is a wardrobe essential that glides effortlessly between seasons. “I hate the idea of hanging up my summer dresses right away,” Gayot tells TZR. Her favorite slip dress is the J.Crew’s Gwyneth Cupro design. "It’s a year-round staple for me. In summer, I wear it alone and in fall, I layer a cashmere sweater over, sometimes shrunken, sometimes oversized. I also love it with a cropped cardigan, a blazer, and a trench coat.”

Sargeant PR Founder Cory Sargeant also leans on the slinky silhouette for transitioning her style to autumn. “I like to incorporate my summer pieces that are easy for layering and a slip dress that can easily be paired with a turtleneck underneath or a knit sweater on top,” she notes.

The Mini Skirt

Among the more notable silhouettes this season is the mini skirt, championed by brands like Miu Miu and Prada. Although bare legs feel out of place in winter, for those earlier months of autumn when the weather still allows a flash of skin, Gayot says the mini skirt is a go-to. “It can be dressed up or down. Made classic or sexy. I think it’s super cool,” she says of the brand’s Marco skirt, designed in a slip shape and with a matching button down. “The skirt alone is great with other pieces like a cashmere tee, a racer back tank, heels, or loafers and socks. It’s super ‘90s modern.”

The Long Dress

For summer days when the weather is giving hot humidity, sometimes a long, breezy dress is the best for effortlessness and a little sun protection — but it’s also fabulous for fall. “I wore a lot of ankle-length dresses with sneakers this summer and I'd love to incorporate them into my fall wardrobe,” Sargeant says. “I’ll be styling my long dresses with a Mary Jane pump and long coat for evenings out with friends.”

The Chunky Sandal

Sleek, strappy sandals are great for event dressing or a tropical vacation, but when it comes to summer footwear that can get you throughout the day as comfortably and cleanly as possible, chunky sandals are the best route to take. “They’re a perfect staple that go with everything for summer, from city to holiday,” Shop Le Point Founder Pauline Montupet says (the pair in her current rotation is from Simon Miller). "I wear them with some loose trousers or a dress for work and some long shorts and a bikini top for the pool. For fall, I am all about layering come cool socks underneath (like these from Socksss). I love a neutral gray or tan sock with the white sandal.”

The Lightweight Blouse

The secret to surviving summer’s most brutal temperatures is breathable, lightweight fabrics — and when layered, they can also adapt to autumn style. “I wore a lot of open lightweight blouses as jackets this summer,” Sargeant shares. “For fall, I’ll wear the blouses buttoned with a boxy trouser or flared jean for a client meeting.” Same goes for Anderson-Boone. “My biggest summer-to-fall essential is a button-up from Comme Si co-designed by Danielle Goldberg. It's the perfect fabrication to feel a breeze and bundle up,” she shares.

The White Tank

Despite its innate simplicity, the white tank has had a profound impact on fashion and personal style in recent months. In part, this can be chalked up to its inclusion in the Prada Spring/Summer 2022 runway — who can forget Hunter Shafer’s finale look? But beyond designer stamps of approval, the white tank has remained a versatile wardrobe staple since its early days as a men’s undergarment. For summer, it’s been styled with printed midi skirts and denim shorts; come autumn, the layering hero will play nicely with everything from button-down shirts and blazers to pantsuits with architectural jewelry. In other words, hold on tight to the sleeveless style.

The Crop Top

Layering hits its stride when it comes to conventionally warm-weather pieces like crop tops. “There is no denying the crop top (and bra top) is back. For summer, I’m pairing it with loose trousers and high-waisted skirt so that the look still feels sophisticated,” Montupet says. “The easiest way to style the crop top for fall would be to wear a blazer over it, but I think it's more fun to layer something under. A tie-back scarf style would be perfect worn over a button down, and a bandage bra style I would layer over a mesh long sleeve top or turtleneck.”

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