
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.
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ZARA
High Collar Bomber Jacket
Princess Polly
Enlightened Faux Suede Bomber Jacket
Maeve
Imara Faux-Suede Funnel-Neck Jacket
Nordstrom
Belted Stretch Cotton Short Trench Coat
Sam Edelman
Faux Leather Anorak
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.
adidas
Taekwondo Mei Ballet Flat
Franco Sarto
Tinsley Mary Jane Flat
Marc Fisher
Jaynie Almond Toe Loafer Mule
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.
Reformation
Clara Cashmere Crew Cardigan
Caslon
Wool & Cashmere Blend Cardigan
Barbour
Woodhouse Wool & Cashmere Crewneck Sweater
COS
Cashmere V-Neck Cardigan
STAUD
Serrano Relax Fit Cashmere Crewneck Sweater
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.
Steve Madden
Brax Pointed Toe Boot
Marc Fisher
Daynna Knee High Boot
Frye
Kate Block Heel Boot
Frye
Campus Knee High Riding Boot
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.
Madewell
Handwoven Leather Tote
JW PEI
Large Nala Faux Leather Wide Tote
Madewell
The Lexington Leather Tote
STAUD
Maude Suede Tote Bag
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