Summer to Fall Transitional Outfit Ideas

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When September hits, I start craving fall fashion, even if the temps are still in the 80s. I want the cozy layers, the richer textures, and the moody colors, but I also don’t want to sweat through my outfit. That’s where summer to fall transitional outfits come in. The goal is to pull in fall-inspired pieces without sacrificing comfort in the lingering heat.

Here are 10 styling tips that make it easy to bridge that tricky summer-to-fall gap.

Summer to Fall Transitional Outfit Ideas

1. Swap Sandals for Sneakers

Sneakers instantly read less “beach day” and more “back-to-school,” making them the perfect swap when you’re craving fall. Pair white tennis sneakers with denim or a midi skirt (these are my go-to sneakers right now), or try a retro sneaker like these for a more polished look. They’re just as comfortable as sandals but have more of an autumn flare.

2. Add a Belt

Summer is all about breezy, flowy dresses and relaxed fits. But adding a belt can transform those same pieces into something more structured and seasonal. Cinch a flowy dress at the waist or add a belt to trousers with a tucked-in tank. This small detail gives your look more polish, moving it from “beach casual” to “fall chic.” This is a classic leather belt that I find goes with almost everything.

3. Add a Cardigan or Blazer

You don’t have to fully commit to layers to get the fall look. Toss a cardigan over your shoulders or drape a blazer on top of your outfit–no need to actually wear them all day. This trick makes any look more seasonal, even if the cardigan spends most of the afternoon hanging off your shoulders. It works especially well paired with a belt (like I mentioned above).

Here are other ways to style a cardigan and more on what to wear under a blazer.

4. Wear a Button-Down

Button-downs are the perfect transitional wardrobe piece that you probably already have on hand. Choose lightweight fabrics like cotton or linen for breathability (this is my favorite lightweight but still structured button-down), but let the long sleeves give your outfit a touch of fall. You can wear them tucked into jeans, or paired with denim shorts if you’re not ready to put those away from the season. Here are other ways I love to style a button-down.

5. Try Wide Leg Jeans Instead of Denim Shorts

Denim shorts are the uniform of summer, but wide leg jeans are just as comfortable in my opinion and feel much more transitional. The loose, breathable fit still works in warm weather, and they pair beautifully with tanks, tees, or even sleeveless sweaters. You get the vibe of denim without the “still at the pool” energy of shorts. All of my favorite (and more flattering) wide-leg jeans are in this roundup.

6. Embrace Barrel Jeans

If you’ve been hesitant to try barrel jeans, this transitional season is the perfect time, and I actually just got these mid-rise barrel jeans and LOVE them. The airy shape keeps them cool, while the structured cut makes them look fall-ready. Pair them with a fitted tee or tank, then add leather mules to balance the silhouette. They’re trendy, comfortable, and a great swap when you’re over shorts but not ready for tighter jeans. (Here are more tips to style barrel jeans.)

7. Try Unexpected Pairings with Shorts

If you’re not ready to let go of shorts, keep them in rotation but style them in unexpected ways. Pair denim shorts with a trench coat, or tuck a sweater into tailored shorts. A crisp button-down buttoned to the top with shorts feels preppy and fresh. (And you know I love preppy fashion.) The contrast of long sleeves or layered tops with bare legs creates that perfect early-fall balance. Bonus style points for styling them with classic loafers, like my favorite Loraine loafers from Sam Edelman.

8. Swap in Fall Colors

Color does a lot of the heavy lifting for seasonal dressing. While your floral dress may feel summery, the exact same silhouette in oxblood or olive green feels instantly autumn. Case in point: I have the floral version of Tuckernuck’s Sofia top, but the oxblood colorway is so perfect for fall. Even if you’re wearing sleeveless tops or lightweight fabrics, shifting to deeper colors makes the outfit feel right for the season.

9. Try a Mule Loafer or Suede Heel

Wedges and strappy sandals feel summery, but swapping them for a mule loafer, block heel, or suede pump changes the vibe instantly. They’re breathable enough for warm days but bring in the polish and texture of fall footwear. A mule loafer with wide leg jeans or a suede block heel with a midi dress can totally transform the look. You could even pair loafers with socks– but I’d throw those on with a dress, skirt or shorts so you don’t totally melt.

10. Add Suede Accessories

Even if you’re still in shorts and a tee, suede adds a fun fall texture to your outfit. Think crossbody bags, belts, or loafers. Swap a straw tote for a suede clutch, or pair ballet flats (like these suede ones from Larroude I own and love) with wide leg jeans. It’s subtle, but the fabric shift reads fall without adding any actual warmth.

Final Thoughts

Even if you’re not ready to break out the knee-high boots, you can still lean into fall fashion. It’s all about textures, colors, and styling tricks that feel seasonal without overheating you. With a few simple swaps – sneakers for sandals, suede for straw, rich solids for florals – it’s easier to embrace pumpkin spice vibes when it’s still melt-your-face-off weather.

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