Summer To Fall Transition Outfits: How to Dress In Between Seasons
I always find it hard to pick out outfits in between seasons. Towards the end of summer, all the fall pieces start hitting the shelf, and I want to wear sweaters and boots! However, summer temperatures usually stick around for a while—especially in California! So what’s a fall-loving girl to do? I’m sharing my tips for how to dress in between seasons and summer to fall transition outfits!
*Updated Sept 2025. Scroll down for more transitional outfits!
Outfit Details: Equipment Blouse c/o thredUP | Faux Leather Skirt via Nordstrom (option) | White Booties (similar) | A.P.C Bag via Shopbop | Ray-ban Sunglasses
How to Dress for Fall When It’s Still Hot Outside
Choose Fall Colors
When summer ends, I always reach for autumnal hues and neutrals. In the above outfit, I chose a brown and tan neutral color palette. A few of my favorite fall colors are burgundy, mustard, dark green, and navy, so you’ll see many of these shades in the coming months!
Choose Fall Fabrics, Prints, and Textures
I always gravitate towards corduroy, leather, velvet, and wool to add a little “fall” to my outfit. It’s time to put away the linen folks! Of course, I think these fabrics need to be used in moderation or else you run the risk of overheating! In the outfit above, I went with a faux leather mini skirt. I still get that luxe look, but my legs are bare, so it’s still appropriate for the 80-degree weather. Another option could be a corduroy or suede skirt or even wool shorts!
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Another option is to choose lightweight, long-sleeved tops in fall colors—like the top I’m wearing in today’s outfit. I chose a lightweight silk blouse in a light brown snakeskin print. Even though it’s long-sleeved, it still feels really light and breezy. I also think the snakeskin print gives it a textured appearance—and texture is always great in fall outfits!
Switch Up Your Shoes
If you want to start dressing for fall, put away the sandals and open-toed shoes. Opt for booties, closed-toe pumps, or loafers. I love breaking out my booties when summer starts coming to an end! Even when the weather is warm, I still feel comfortable in them.
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I chose white booties for this outfit because I liked the contrast. I think the white makes them “pop” more in this outfit. These are actually off white or bone colored, so they are not stark white. I think they work great as a fall/winter bootie!
Choose Lightweight Jackets or Blazers
When the weather starts to get a little cooler, you can start adding lightweight layers to your outfit. I always love a trench coat with a fall outfit. There are lots of options now lengthwise. I love both a short and a long trench.
And, of course, the good ol’ blazer. I’m OBSESSED with blazers. They are the perfect lightweight jacket option if you don’t feel like wearing a traditional jacket. You can find blazers in lightweight fabrics like tencel and switch to heavier wool jackets when the weather cools.
Summer To Fall Transition Outfits
Here are some of my favorite summer-to-fall transition outfits from years past. I’ve incorporated the tips above into these looks.
Summer dress + trench coat outfit
Original post: Summer to Fall Transition Dress
This dress from DOEN is a great example of a summer-to-fall dress. It’s sleeveless and breezy enough for summer with the buttons down the front, but can also be layered up for fall. The print is perfect – with browns and deep oranges that work for late summer and fall. I wear this dress with sandals and a straw bag in the summer, and then add boots and a trench coat for fall. I’ve also layered light turtleneck sweaters underneath the dress for cooler fall days.
Summer Dress + Blazer Outfit
Original post: How to Wear Thigh High Boots
Another one of my favorite summer-to-fall dresses is this cotton plaid dress from Jenni Kayne. The plaid print and colors scream fall, but the cotton fabric and slip dress style make it appropriate for summer. In the summer, I wear this dress with sandals; in the fall, I swap them out for ankle or knee-high boots!
White Midi Skirt Styled for Fall
Original post: How to Style a White Midi Skirt for Fall
Don’t put away those white midi skirts just yet! You CAN wear white after Labor Day and even transition it into fall. The key is to add layers, fall shoes, and fall colors to your white midi skirt to make it fall-appropriate. In the first example, I’ve added a cotton sweater, a light cotton jacket for the layers, and ankle boots in brown suede for some nice texture. In my second look, I added a long-sleeved shirt and a sweatshirt for my light layers and switched out sandals for flats.
Long Denim Shorts + Sweatshirt
Don’t put away your shorts just yet! A pair of long denim shorts can be styled for fall by changing your shoes and adding layers. I’m wearing slingback loafers, a great transitional shoe! Business in the front, party in the back. I’ve traded my summer blouses for a relaxed cotton button-up shirt and added a cotton sweatshirt for some extra warmth. I also switched out my summer straw bag for a neutral leather bag.
Relaxed Trousers + T-Shirt Outfit
This has been one of my favorite transitional outfits as of late. I just picked these trousers up from Sézane’s new fall collection, and even though they are a wool blend, they’re light enough to wear in early fall. They also have a relaxed, sporty vibe, which goes well with a cropped tee and sneakers.
