The Key Pieces Fashion Insiders Are Buying for Transitional Weather

There’s something bittersweet about the end of summer, which means goodbye to beach days, sun-kissed skin, and 9 P.M. sunsets. At the same time, it’s the start of something new—a chance to tuck tank tops and swimsuits into the back of the closet in exchange for transitional pieces that will seamlessly take wardrobes into fall. For a handful of our favorite fashion insiders, that in-between-the-seasons vibe can look somewhat different, as everyone has a unique way of embracing the drop in temperatures while saying “see you later” to summer.

From consultant Sandrine Charles’s streamlined essentials, including Bottega Veneta’s Hop bag and Toteme’s classic black tee, to Shopbop senior fashion director Caroline Maguire’s fun-meets-practical aesthetic—cue Damson Madder’s shrunken Rugby shirt—there are a myriad of ways to venture into cooler weather in style. And if you’re anything like fashion writer and founder of NEVERWORNS, Liana Satenstein, recycling pieces that are already in your possession is key. Read on to see what these ladies and others are eyeing right now.

“My vibe is everyday classic for fall,” says consultant Sandrine Charles, the founder of her namesake consulting company and co-founder of the Black in Fashion Council. “I want to focus on key pieces versus hyper-trends to streamline my closet and wardrobe.” For her, that means relying on her favorite Acne Studios boots (she owns them in two colorways—shiny leather and croc-embossed), a Flattered belt that pulls together her daily look of jeans or trousers, and a Bottega Veneta Hop bag that she’s used for work for about a year now. “It’s fully equipped with all things like a makeup bag, flats, extra gym clothes, my laptop, etc.,” she says. Last but not least, Charles is investing in Toteme’s classic black tee, which she pairs back with slacks, skirts, and jeans for her day-to-day meetings.

“I’m channeling an aesthetic that emulates effortless yet elevated,” says Shopbop Senior Fashion Director Caroline Maguire. “I love being authentic in my personal style—staying true to what feels right with pieces that transition seamlessly from day to night or season to season.” Case in point: Le Bop’s Dree Mid-Length Barn Jacket with its unexpected pop of blue at the collar, Liffner’s Large Belted Bucket Bag (“I absolutely love summer suede,” says Maguire) and Reformation’s Jessie Thong sandals. Maguire is not shy to admit that she jumped on that footwear trend fast and is not ready to let it go just yet. Catch her this fall styling them with jeans and a Damson Madder shrunken rugby shirt. “It’s lightweight, effortless, and endlessly wearable!”

“The vibe is just staying warm in case of a sudden temp drop,” says writer Liana Satenstein, whose current staples include a “very vintage” Banana Republic khaki trench that she can roll up and stuff in her bag whenever she needs to, a trusty Levi’s ’90s-style denim trucker jacket that’s been in her arsenal for eons, and Maharishi cargo pants she’s been wearing on repeat with Tory Burch Reva ballet flats. “My toes cannot be saved by any pedicure and it kind of gets chilly at night so the thin flats are my savior.”

“During this transitional time period, I am going for a corporate maximalist vibe,” says publicist and entrepreneur Gia Kuan. That means zeroing in on a pair of August Barron boots. “They just look so comfortable, and my wardrobe is g percent black clothes and accessories, as I usually focus on color. So if I wear black, it has to have something extra.” Additionally, Kuan is eyeing Panconesi Vacanza’s stone necklace and a bold, sculptural heart-shaped Chopard watch from the ’80s. “I am not really a watch girl, but if I wear one, I want it to make me want to look at the time,” says Kuan. To top off her look, she’s going for a Dries Van Noten purple trench, as she can’t go a season without a statement coat that stands out with color, texture or shine.

“For fall, I’m investing in styles that feel casual but have intentional—luxe details in silhouette or fabrication,” says fashion consultant Michal Kurtis. “Think a structured square toe on Khaite’s Colt ankle boot or Kallmeyer’s drawstring pant done up in taffeta.” Like Maguire, Kurtis has also leaned into summer’s flip-flop trend, and once the temperature drops, you can find her in a pair of cozy A.Emery slides. On lazier days when she submits to a sweatshirt, she plans to offset the casualness with a pair of Kiko Kostadinov earrings. “I always want my outfits to feel effortless while having elements that look incredibly considered,” she says.

Every product featured on ELLE.com is independently researched, tested, or editor-approved. We only recommend products that we stand behind, and the merchandise featured on our site is always driven by editorial and product testing standards, not by affiliate deals or advertising relationships. Any content created in partnership with advertisers is marked as such.