5 Chic Summer-to-Fall Transitional Pieces Fashion People Are Shopping in August
Fall is right around the corner. If you're looking to gear up for the coming months, you've landed in the perfect place. Transitional dressing can be a little tricky, as most people find it difficult to manage the switch between seasons. I utilized my fashion and shopping expertise to help you carry your current summer favorites into the new season seamlessly by finding the top transitional-weather picks to focus your closet refresh on.
It doesn't take a lot to achieve peak between-season fashion, so I'll tell you exactly what you should buy and where to buy high-quality, editor-approved versions of each item. I recommend investing in versatile jackets, flat shoes, lightweight knits, tall boots, and a beautiful leather tote to really step into the fall vibes. Keep scrolling to shop summer-to-fall transitional clothing today.
Shop Summer-to-Fall Fashion
Versatile Jackets
An easy jacket is the perfect way to make your go-to pieces fall-friendly. For fall 2026, funnel-neck silhouettes have been trending in various fabrications. However, you can't go wrong with other timeless styles.
Flat Shoes
Trade your favorite sandals in for a solid flat-shoe style. Whether it's loafers, Mary Janes, ballet flats, or mules, there's endless potential for styling with this shoe category. I love wearing fun socks to give my outfit a little extra personality.
Lightweight Knits
As the leaves turn, sweater weather ensues. Having go-to lightweight knits can make the biggest difference when weather conditions start to shift. You can't go wrong with cashmere, and either a cardigan or crewneck is a perfect place to start.
Tall Boots
Boots are quintessentially fall, and I'm partial to taller styles. Pair your favorite boots and tights with cute trouser shorts, skirts, and dresses from the last few months to give them that autumn treatment.
Leather Tote
It's officially time to retire your raffia and straw carryalls for a fall- and winter-friendly leather or suede tote. Classic colorways, like luxe black or warm, rich brown, won't disappoint.

Chinazor "Chichi" Offor is a Georgia-born, Los Angeles–based associate editor who relocated from Brooklyn, New York, and joined Who What Wear's West Coast office in 2022. At WWW, she utilizes her years of editorial experience to interview trending talent, explore trends, and curate shopping guides. Chichi previously worked at Refinery29, where she helped revolutionize the brand’s plus-size and inclusive fashion coverage. In her spare time, she’s keeping up with the latest movie releases, enjoying a relaxing day at the spa, or obsessing over her latest ADHD-fueled hyper fixation (e.g., Jesse McCartney's underrated career, the negative effects of bicoastal intellectual elitism, and Gen Z’s loneliness epidemic). You can find her online @thechichio on Instagram & TikTok.