If I Saw You in Any of These 15 Summer-to-Fall Transitional Outfits, I'd Think You Hired a Stylist

Nice taste.

A collage of women wearing summer-to-fall transition outfits.
(Image credit: @shayinjune; @nlmarilyn; @annabelrosendahl; @brittanybathgate; @sylviemus_; @deborabrosa; @courtneygrow)
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It might feel like summer just started (or is that just me?), but whether we like it or not, fall is approaching, and I, for one, don't want to wait until the last minute to start planning my autumn outfit rotation. Instead, I like to get to preparations early—so early, in fact, that I often begin wearing fall pieces when it's still technically summer. Think tissue-thin knits styled with a leather skirt or a lightweight jacket paired with trousers and flip-flops. Transitioning from summer to fall with ease is a fine art, and fortunately for, well, everyone, I follow all the masters at it.

Ahead, prepare to discover the ultimate outfit guide to fall-to-summer transitional outfits in 2025. There are button-down shirts styled with calf-hair skirts, sundresses paired with barn jackets, and car coats styled with V-neck sleeveless shirts and sandals. There is a sartorial science to dressing during that confusing period between late summer and early fall, and the fashion people below have the equation memorized. Keep scrolling if you want to be the next expert on the subject. (Trust me, you do.)

@shayinjune wearing a gray button-down shirt with black trousers and flip-flops.

(Image credit: @shayinjune)

Get the look: Gray button-down shirt + black wide-leg trousers + flip-flops

@nlmarilyn wearing a sporty ivory-colored jacket with black trousers and open-toed heels.

(Image credit: @nlmarilyn)

Get the look: Sporty jacket + black flare trousers + open-toe heels

@leiasfez wearing a collared knit sweater with a leather skirt.

(Image credit: @leiasfez)

Get the look: Collared sweater + leather pencil skirt + heeled sandals

@_marisamartins_ wearing a white T-shirt with a long black denim skirt and flip-flops.

(Image credit: @_marisamartins_)

Get the look: Oversized white T-shirt + black denim maxi skirt + flat sandals

@courtneygrow wearing a sheer dress and a khaki barn jacket.

(Image credit: @courtneygrow)

Get the look: Barn jacket + white sheer dress + cord necklace

@deborabrosa wearing a white eyelet dress with black trousers.

(Image credit: @deborabrosa)

Get the look: Eyelet dress + black trousers + heeled sandals + shoulder bag

@stephaniebroek wearing a white button-down shirt with a cow-print skirt an tights.

(Image credit: @stephaniebroek)

Get the look: Button-down shirt + calf-hair skirt + tights + kitten-heel pumps

@elizagracehuber wearing a black leather blazer, navy sweater, and cream lace-trim shorts.

(Image credit: @elizagracehuber)

Get the look: Leather blazer + lightweight sweater + lace-trim shorts

@annabelrosendahl wearing a cream trench coat, red T-shirt, and black capri pants.

(Image credit: @annabelrosendahl)

Get the look: Red T-shirt + ivory coat + capri pants + flats

@hannahlewisstylist wearing a cream coat, white eyelet top, and black trousers.

(Image credit: @hannahlewisstylist)

Get the look: Crochet top + ivory coat + black trousers + flip-flops

@iliridakrasniqi wearing a white button-down shirt with flare jeans and sandals.

(Image credit: @iliridakrasniqi)

Get the look: White button-down shirt + flare jeans + heeled sandals

@sylviemus_ wearing a black blouse and a leather skirt.

(Image credit: @sylviemus_)

Get the look: Black blouse + leather pencil skirt + strappy heels

@hannamw wearing a black coat, V-neck top, and black trousers.

(Image credit: @hannamw)

Get the look: V-neck top + black coat + flare trousers + silver necklace

@brittanybathgate wearing a white T-shirt, black dress, and red flip-flops.

(Image credit: @brittanybathgate)

Get the look: White T-shirt + maxi dress + red flip-flops

@lindatol_ wearing a white tee, trench coat, and wide-leg jeans.

(Image credit: @lindatol_)

Get the look: Trench coat + white T-shirt + wide-leg jeans

This post was published at an earlier date and has since been updated.

Eliza Huber
Senior Fashion Editor

Eliza Huber is an NYC-based senior fashion editor who specializes in trend reporting, brand discovery, and the intersection of sports and fashion. She joined Who What Wear in 2021 from Refinery29, the job she took after graduating with a business degree from the University of Iowa. She's launched two columns, Let's Get a Room and Ways to Wear; profiled Dakota Fanning, Diane Kruger, Katie Holmes, Gracie Abrams, and Sabrina Carpenter; and reported on everything from the relationship between Formula One and fashion to the top runway trends each season. Eliza lives on the Upper West Side and spends her free time researching F1 fashion imagery for her side Instagram accounts @thepinnacleoffashion and @f1paddockfits, watching WNBA games, and scouring The RealReal for discounted Prada.

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