The stretch between late summer and the official start of fall on September 22nd is a whirlwind of totally unpredictable weather. You go from overheating in the sun to pulling on a sweater in an over-air-conditioned office, and by evening, it’s pouring rain. So while the days of throwing on your favorite sundress and heading out the door are behind us, outfit planning for the in-between season doesn’t have to be arduous. Transitional pieces to the rescue! Lightweight, layer-friendly, and chic, they’re perfect for effortlessly bridging the gap between seasons. We got the inside scoop from fashion experts on their most-loved transitional items and how they style them to feel comfortable and put-together.
Maxi Dresses in Floating Fabrics
“Don’t tuck away your summer dresses just because summer is almost over,” says Stamko. In fact, Mensch notes that the secret to mastering the in-between season is “embracing the contradiction.” Where to start? Choose a maxi dress in floating fabrics. The length says fall, the weight says summer, she says. Another way Mensch makes maxi dresses feel more fall-forward: “Hang on to summer silhouettes but switch up the colors.” For example, opt for a long, flowy maxi dress in autumn shades, such as “rust, mustard, or olive,” she notes. On a chillier day, you can throw a cardigan or a light jacket over maxi dresses for an elegant, but still weather-appropriate, look.
Jean Jackets
A wardrobe staple for decades, Stamko deems the jean jacket the “ultimate layering piece” for in-between weather. A worn-in jean jacket is “light enough for daytime but cozy enough for when the sun goes down,” she says. The greatest thing about the jean jacket is its versatility: you can wear it over just about everything, from a mini dress to a matching sweat set. They are also totally durable! I still wear my mom’s from the ’80s, and it’s held up perfectly. Plus, I love its distressed look. For a more polished silhouette, Stamko loves “throwing a denim jacket over a loose blouse and straight-legged pants, and finishing it off with a pair of wedge heels or loafers.” Simple but effective.
Loose Blouses
Stamko embraces the light, airy movement of a blouse to balance heavier fall staples like ankle boots and outerwear. Just like with maxi dresses, follow Mensch’s advice and trade in summery whites and pastels for deeper, seasonal tones like “mocha brown, paprika, or burnt sienna.” She calls it the “easiest transformation in fashion: same pieces, autumn colors, completely different energy.” For a polished yet effortless feel, tuck your blouse into high-waisted jeans and layer with a light jacket—or soften the silhouette with a cozy cardigan, Stamko suggests.
Short Sleeve & Sleeveless Knit Tops
“Whoever invented these deserves a Nobel Prize,” says Mensch. Short-sleeve and sleeveless knit tops strike the perfect balance—more polished than a T-shirt, yet lighter than a sweater. They’re ideal for transitional weather: cozy without being stifling. And just like a tee, they pair seamlessly with everything—from a maxi skirt on warm days to jeans or trousers when the temperature drops. All the comfort of a sweater, no sleeve-drama, Mensch adds.
