If I spotted you in any of these 15 outfits perfect for transitioning from summer to autumn, I would assume you had a stylist.
It may seem like summer has just begun (or is it just me?), but whether we want it to or not, autumn is on the way, and I personally prefer not to postpone planning my autumn wardrobe until the last moment. Instead, I like to start prepping early—so much so that I often start wearing autumn items even while it’s still technically summer. Imagine lightweight knits paired with a leather skirt or a breezy jacket combined with trousers and flip-flops. Yes, smoothly transitioning from summer to autumn is an expert skill, and luckily for everyone, I follow the pros who excel at it. Ahead, get ready to explore the ultimate outfit guide for autumn-to-summer transitional styles in 2025. Expect to see button-down shirts with calf-hair skirts, sundresses with barn jackets, and car coats layered over V-neck sleeveless tops and sandals. Dressing during that tricky phase between late summer and early autumn involves a certain fashion science, and the style experts below have mastered the formula. Keep scrolling if you aspire to become an authority on this topic. (Trust me, you'll want to.)
**The Best Summer-to-Autumn Transitional Outfit Ideas to Emulate in 2025**
1. **Button-down shirt + Wide-leg trousers + Flip-flops**
**Style Notes:** First up, a look showing how soft tailoring can create a fantastic transitional outfit. I particularly enjoy the juxtaposition of Shay's gray shirt with sharp black trousers, providing a darker take on traditional monochrome.
**Shop the Look:**
- H&M: Oversized Lyocell Shirt – Light enough for sunny days yet offers ample coverage.
- COS: Wide-Leg Cotton Trousers – These will be an essential for autumn and winter.
- The Row: Dune Flatform Sandal – Flip-flops lighten this look.
2. **Sporty jacket + Flares + Open-toe heels**
**Style Notes:** If you invest in only one jacket trend this year, make it a sporty zip-up style. They are not only practical (goodbye, waterproof worries), but they also work perfectly with smart casual pieces, as Marilyn demonstrates.
**Shop the Look:**
- Alo: Origin Full-Zip Track Jacket – Designed to be breathable for transitional weather.
- & Other Stories: Kick Flare Trousers – Flares offer a playful twist on traditional wide-leg trousers.
- Toteme: Leather Thong Sandals – Perfect for now and for the upcoming party season.
3. **Collared Sweater + Leather Skirt + Heeled Sandals**
**Style Notes:** I envision this outfit suitable for many autumn events, from dinner outings to office wear (just swap heels for ballet flats). It’s a versatile choice for those in-between days.
**Shop the Look:**
- Reformation: Hermia Regenerative Merino Polo – A quintessential preppy piece.
- Norma Kamali: Straight Skirt – This style transitions well from day to night.
4. **White T-shirt + Denim Maxi Skirt + Flat Sandals**
**Style Notes:** On days when you're uncertain about what to wear, take a cue from Marisa and reach for reliable staples like her T-shirt and denim skirt.
**Shop the Look:**
- Helsa: The Sculpted Tee in Thick Jersey – The wide sleeves elevate this simple tee.
- Russell & Bromley: Radford Leather Flip-Flop – Wear with flip-flops now, then switch to trainers and ballet flats as it gets colder.
5. **Barn Jacket + Sheer Dress + Cord Necklace**
**Style Notes:** A sheer dress may seem unconventional for autumn, but Courtney shows how a lightweight jacket can effectively transition it.
**Shop the Look:**
- Topshop: Barn Jacket With Buckle Detail – Opt for an oversized fit for a relaxed vibe.
- SWF: Cap Sleeve Midi Dress – For underneath, choose undergarments in a similar shade for a cohesive look.
- Juju Vera: Petra Sterling Silver Shell Necklace – Finish the outfit with a statement necklace.
6. **Lace Dress + Trousers + Heeled Sandals**
**Style Notes:** Another way to extend the life of your favorite summer dresses is to layer them over trousers, as Debora has done.
**Shop the Look:**
- H&M: Tie-Strap Broderie Anglaise Dress – The scallop trim on this lace dress is charming.
- Reformation: Vida Low Rise Pant – Low rise styles are back in vogue.
- Toteme: Leather Bandeau Slides – A great elevated basic.
7. **Button-down Shirt + Printed Midi Skirt + Pumps**
**Style Notes:** The cow print trend will carry into AW25, so get ahead by styling a printed skirt with a white shirt and heels—tights are optional until it
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Pleasant flavor.
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If I spotted you in any of these 15 outfits perfect for transitioning from summer to autumn, I would assume you had a stylist.
Great flavor.