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
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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H&M
Oversized Lyocell Shirt
Light enough for sunny days yet with plenty of coverage.
COS
Wide-Leg Cotton Trousers
These will be a staple all autumn winter.
The Row
Dune Flatform Sandal
Flip flops give this look a lighter touch.
2. Sporty jacket + Flares + Open-toe heels
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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Alo
Origin Full-Zip Track Jacket
Alo’s zip jacket is designed to be breathable, making it ideal for in-between weather.
& Other Stories
Kick Flare Trousers
Flares make a playful alternative to traditional wide-leg trousers.
Toteme
Leather Thong Sandals
Wear these now and when party season rolls around.
3. Collared Sweater + leather Skirt + Heeled Sandals
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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Reformation
Hermia Regenerative Merino Polo
The perfect preppy wardrobe staple.
Norma Kamali
Straight Skirt
This style will see you from day to night.
4. White T-shirt + Denim Maxi Skirt + Flat Sandals
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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Helsa
The Sculpted Tee in Thick Jersey
The wide sleeves elevate this simple tee.
Switch your favourite jeans for a denim skirt instead.
Russell & Bromley
Radford Leather Flip Flop
Wear with flip flops now, then trainers and ballet flats on colder days.
5. Barn jacket + Sheer dress + Cord Necklace
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Topshop
Barn Jacket With Buckle Detail
Go oversized for a relaxed feel.
SWF
Cap Sleeve Midi Dress
Wondering what to wear underneath? Opt for underwear in a similar shade for a tonal look.
Juju Vera
Petra Sterling Silver Shell Necklace
Don’t forget to finish with a statement necklace.
6. Lace Dress + Trousers + Heeled Sandals
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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H&M
Tie-Strap Broderie Anglaise Dress
How pretty is the scallop trim on this lace dress?
Reformation
Vida Low Rise Pant
Low rise is officially back.
7. Button-down Shirt + Printed Midi Skirt + Pumps
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WNU
The Boyfriend with Exaggerated Cuff
Dries Van Noten
Printed Wool-blend Midi Skirt
The abstract nature of Dries Van Noten’s cow print skirt makes it feel chic and elevated.
Massimo Dutti
Leather High Heel Mules
These look subtly ’80s-inspired.
8. Leather Blazer + Sweater + Lace-Trim Shorts + Courts
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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Reformation
Veda Louisa Leather Jacket
Reformation
Fern Satin Short
I’m in love with these cute lace shorts.
I love the contrast of a chunky ballet flat against the delicate shorts.
9. Trench Coat + T-shirt + Capri Pants + Flats
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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Toteme
Cotton-blend Trench Coat
The fash pack love a trench coat.
Ideal for adding a pop of colour.
Aligne
Savannah Ponte Capri Pants
Not too short, not too long.
10. Coat + Crochet Top + Trousers + Flip-Flops
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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Róhe
Single-breasted Coat
A cream coat feels perfect for this transitional season.
Don’t save this top just for summer.
I’ not sure I can give anymore proof that you need a pair of hardworking black trousers.
11. Button-down Shirt + Flared Jeans + Heeled Sandals
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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MANGO
Cotton Button-Up Shirt
A capsule wardrobe staple.
Reiss
Bonnie Mid-Rise Flared Jeans
Indigo blue tones are great for autumnal days.
Mango
Stiletto Heel Sandal With Buckle
Sleek, simple and undeniably sexy.
12. Black Blouse + Pencil Skirt + Strappy Heels
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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With Nothing Underneath
The Boyfriend: Silk Satin, Onyx
MANGO
Faux-Leather Pencil Skirt
This may be faux leather but it looks as good as the real thing.
Next
Skinny Signature Premium Leather Strappy Heels
13. Coat + V-neck Top + Flares + Sandals
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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COS
Single-Breasted Car Coat
A great staple black coat.
These stretch for added comfort.
14. White T-shirt + Maxi Dress + Red Flip-Flops
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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COS
Ruffled Cotton Midi Dress
I love the loose fit of the maxi dress.
Ancient Greek Sanals
Saionara Jelly
If you are braving sandals, jellies will wipe clean in any unexpected downpours.
15. Trench Coat + White T-shirt + Wide-Leg Jeans + Sandals
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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MANGO
Long Double-Breasted Trench Coat
A great high street option.
Great basics needn’t cost a lot.
Reformation
Cary High Rise Slouchy Wide Leg Jeans
You’ll get plenty of wear out of these.
