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

Not sure what to wear during that confusing period between summer and autumn? Here are 15 transitional outfit ideas to copy now. You're welcome.

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, autumn 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 autumn 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. Yes, transitioning from summer to autumn 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 autumn-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 autumn, and the fashion people below have the equation memorised. Keep scrolling if you want to be the next expert on the subject. (Trust me, you do.)

The Best Summer-to-Autumn Transitional Outfit Ideas to Copy in 2025

1. Button-down shirt + Wide-leg trousers + Flip-flops

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

(Image credit: @shayinjune)

Style Notes: First up, a look that proves soft tailoring can come together to create a seriously great transitional look. I especially love the contrast between Shay's grey shirt and crisp black trousers for a moodier alternative to traditional monochrome.

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2. Sporty jacket + Flares + Open-toe heels

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

(Image credit: @nlmarilyn)

Style Notes: If you only invest in one jacket trend this year, make it a sporty zip-up style. Not only do they deliver on ample practicality (hello, waterproof), but they're also ideal for dressing down smart separates like Marilyn has here.

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3. Collared Sweater + leather Skirt + Heeled Sandals

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

(Image credit: @leiasfez)

Style Notes: I can picture this look working for so many autumn occasions, from dinner and drinks to days in the office (just switch heels for ballet flats). A versatile choice for those in-between days.

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4. White T-shirt + Denim Maxi Skirt + Flat Sandals

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

(Image credit: @_marisamartins_)

Style Notes: On those days when you can't decide just what to wear, take inspiration from Marisa and return to trusty wardrobe staples like her T-shirt and denim skirt combo.

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5. Barn jacket + Sheer dress + Cord Necklace

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

(Image credit: @courtneygrow)

Style Notes: A sheer dress may seem an unconventional choice for wearing into autumn, however, here Courtney shows how a lightweight jacket can make it totally transitional.

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6. Lace Dress + Trousers + Heeled Sandals

@deborabrosa wearing a white eyelet dress with black trousers.

(Image credit: @deborabrosa)

Style Notes: Another great way to get extra fashion miles from your favourite summer dresses is to layer them over trousers, as Debora has here.

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7. Button-down Shirt + Printed Midi Skirt + Pumps

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

(Image credit: @stephaniebroek)

Style Notes: The cow print trend is set to continue into AW25 so why not get ahead of it and style a printed skirt with a white shirt and heels—tights optional until it turns truly chilly.

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8. Leather Blazer + Sweater + Lace-Trim Shorts + Courts

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

(Image credit: @elizagracehuber)

Style Notes: If you were preparing to pack your lace trim shorts away, think again. Simply pair with heavier autumnal fabrics, like Eliza has here, to take them into the new season.

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9. Trench Coat + T-shirt + Capri Pants + Flats

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

(Image credit: @annabelrosendahl)

Style Notes: I'm calling it now, this may be the ultimate fashion girl's transitional uniform. A trusty trench coat, colour pop T-shirt and capri pants? Just perfection.

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10. Coat + Crochet Top + Trousers + Flip-Flops

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

(Image credit: @hannahlewisstylist)

Style Notes: In need of an outfit that can see you through multiple seasons in one day? This is it. Keep your coat on for cold mornings, while the bandeau top will ensure you aren't overheating if the sun does decide to make an appearance.

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11. Button-down Shirt + Flared Jeans + Heeled Sandals

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

(Image credit: @iliridakrasniqi)

Style Notes: In my opinion, it's during the summer to autumn transition when the jeans and a nice top protocol really comes into its own so pull out your best denim like Ilirida has here.

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12. Black Blouse + Pencil Skirt + Strappy Heels

@sylviemus_ wearing a black blouse and a leather skirt.

(Image credit: @sylviemus_)

Style Notes: Another chic leather skirt outfit. Here, Slyvie styles the autumnal must-have with a lightweight blouse for a softer, lighter alternative to a chunky knit.

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13. Coat + V-neck Top + Flares + Sandals

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

(Image credit: @hannamw)

Style Notes: Opting for light fabrics in darker tones is a great way to bridge the gap between your summer and autumn style.

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14. White T-shirt + Maxi Dress + Red Flip-Flops

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

(Image credit: @brittanybathgate)

Style Notes: At this time of year, I'm a big fan of clever layering to get extra wear from your summer pieces. An oversized T-shirt looks just as good worn under a loose-fit dress as layered on top so play around and see what works for you.

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15. Trench Coat + White T-shirt + Wide-Leg Jeans + Sandals

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

(Image credit: @lindatol_)

Style Notes: Lastly, I had to include an outfit which showcases the ultimate transitional cover-up: the trench coat. Paired with a simple T-shirt and jeans, it makes any outfit summer-to-autumn approved.

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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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