14 Summer to Fall Transition Outfits
We summer to fall girlies are THRIVING right now! I love September because, at least here in Boise, the weather provides the perfect opportunity to mix both summer pieces and fall pieces into one outfit. (We can also get lucky and have some of that same transitional weather in August and October.) And yes, I also have a September birthday, but it really is the most wonderful time of year. I do realize I say that about a lot of different times of year, LOL.
If you’re looking for styling tips for your summer to fall transition outfits, you’ve come to the right place! I rounded up 14 of my favorite summer to fall transition outfits from the past few years and shared tips for putting together transitional outfits you’ll LOVE. And yes, some of these outfits may not be entirely in style at the moment, but you can always make tweaks and substitute the older styles for current styles! (And if you’re curious about individual outfit details, click on the photo to go to the original post!)
READ NEXT: 12 Winter to Spring Transition Outfits
14 Summer to Fall Transition Outfits
1. Wear long-sleeved dresses
Are you a dress-loving gal? One of the easiest ways to transition your wardrobe for fall is to pull out the long-sleeved dresses! When the weather cools down, I love wearing long-sleeved tops with shorts (or skirts), and a long-sleeved mini dress has the same vibe. Keep your accessories dark to play up the fall theme!
2. Switch from sandals to boots
A simple shoe switch is all it takes to transition your outfits from summer to fall! I obviously wear a lot of sandals in the summer months like most people, but when I’m feeling fall I switch to darker colored sandals and then ankle boots if the weather cools off enough. Boots even work well with your skirts and dresses!
3. Add a third piece
When the weather finally cools off after a long summer, throw on a third piece to complete your outfit and make a summer outfit feel more like fall! Some of my favorite options include leather jackets, suede jackets, utility jackets, and even blazers, cardigans, etc. Third pieces often make an outfit feel more “complete” than it would look without one.
4. Swap blouses for flannel shirts
In the summer, you probably reach for more linen and lightweight cotton button-down shirts. When the weather starts to turn towards fall, switch those linen and lightweight shirts out for flannel shirts. (A flannel shirt + mini skirt results in a wonderful juxtaposition!) Add accessories that tie into the colors of the flannel!
5. Mix black and brown
Nothing feels more like fall to me than wearing black and brown together (specifically, black with cognac brown). It’s such a rich color combination. Every time I wear it, I feel like I should be sitting in a cafe with a hot chai watching the world pass me by. Lol. It’s one of my favorite color combinations and one of my favorites to make outfits feel more like fall.
6. Wear a faux romper/jumpsuit
Obviously, you can wear a faux romper or jumpsuit at any time of year, but it’s an especially fun outfit combination to wear in late summer or early fall. Opt for a matching top and shorts set in the same fabric, and if you want to really lean into fall, pick long sleeves (or a long pant) and in a darker, moodier color!
7. Wear summer items in darker colors
I own a few summery styles in darker, more autumnal colors (including a chocolate brown dress, black sandals, olive green baseball cap). I love wearing all of them together in the same outfit—it’s a fun nod to fall even when the temperatures are still high! Other darker fall-like colors include navy, burgundy, charcoal, and emerald green.
8. Add a wool or felt floppy hat
I don’t know what it is about wool or felt floppy hats, but as soon as I put one on, the outfit instantly feels like it’s ready for fall. A blouse, denim skirt, and flats can read summer without anything more, but add a felt floppy hat and it’s no longer a summer outfit in my brain! This is another super simple way to transition your summer outfits to fall.
9. Add fall color in the form of one item
If it’s still hot AF where you are and you’re just dying to wear something fall-like but aren’t ready to stop wearing your summer clothes just yet, try adding fall color in the form of only one item in your outfit. It’s an easy-peasy swap! I love reaching for my cherry mahogany tee, it’s the best fall color that goes perfectly with ivory. (Ivory is softer than stark white, which makes it a great base for your summer to fall outfits!)
10. Wear fall items in lighter colors
This is sort of the opposite of wearing summer items in darker colors! Instead, reach for any fall-like items you own (sweatshirts, sweaters, etc.) in lighter, more summery colors, like white, ivory, blush pink, sage green, sky blue, etc. I paired my blush pink cropped sweatshirt with a striped midi skirt and coordinating clog sandals. Fall but make it summer!
11. Contrast white with cognac brown
I mentioned earlier that I love wearing black with cognac brown. On the opposite end of the spectrum, I also love pairing white with cognac brown! White is the ultimate summer color. There’s a really antiquated fashion rule that says you can only wear white between Memorial Day and Labor Day for a reason, right...? Pair white with cognac brown AFTER Labor Day and you’ve successfully transitioned a summer outfit into fall!
12. Mix your textures
Play around with textures when putting together your summer to fall transition outfits! I love thick long-sleeved tees, sweatshirts, cashmere, alpaca blends, denim, canvas, faux fur, velvet, suede, leather—the list goes on. Adding texture always makes my outfits feel like they’re ready for fall, often because it’s simply too hot to wear them in the summer!
13. Add a chambray shirt
Denim is the quintessential fall texture. Ease into fall by pairing your white denim with a chambray shirt. I wear a sleeveless chambray way more often than I wear a long-sleeved chambray (so much so that I don’t even own the latter anymore). If you prefer a long-sleeved chambray, roll up the sleeves a couple of times so it feels more casual.
14. Double your denim
Why not double down on denim and wear TWO blue denim items in the same outfit?! I love a good Canadian tuxedo. When I was looking through my past outfits for this post, this double denim outfit with the cashmere cardigan screamed summer-to-fall to me, and it’s because it’s full of more substantial textures you’d wear most often in the cooler months.