Fall is that magical time of year when the air gets a little crisper, the leaves start turning, and all of a sudden I’m reaching for layers again. It’s the time of year where fashion really shines! You can mix textures, play with colors, and experiment with looks that are equal parts cozy and chic. And just because summer’s wrapping up, that doesn’t mean you have to pack away all your summer faves just yet. In this roundup, you’ll find ways to carry those pieces forward, turning them all into fall transition outfits by making a few smart swaps. They key is to build your closet around a handful of fall essentials that make everything feel fresh without overhauling your entire wardrobe..
Two-Piece Denim Set and Knee-High Boots
A matching denim set makes the perfect look when you’re moving from summer to fall. The sleeveless denim vest and shorts keep things light and structured for warm weather, while the brown vintage-inspired bag and matching faux leather boots bring a touch of autumn.
Denim Vest and Maxi Skirt
I’m obsessed with this chiffon maxi skirt—its floral patchwork design screams fall! Style the skirt with a buttoned denim vest and mid-calf boots to balance out the feminine vibe while keeping it light and casual enough for warm weather.
Knit Cardigan and Skirt Set and Square Toe Boots
A matching knit cardigan and skirt is a cute and easy way to handle this time of year. Wearing a light layer like a cropped cami helps you stay breezy during warmer afternoons. Just add square toe boots and a neutral shoulder bag to bring it all together.
Oversized Cardigan and Leggings
A longline sports bra with high-waisted leggings is the kind of base that’s cute and comfy to wear on repeat during the summer to fall stretch. Add a cozy layer by tossing on an oversized cardigan, and finish off the look with some Oxford New Balance shoes for a laid-back look that’s perfect for errands.
Cropped Puffer Vest and Denim Skirt
To add some instant edge to your look, opt for a black denim skirt and pair it with some knee-high boots. The fitted crewneck long sleeved top adds just the right amount of coverage for a fall transition outfit, and a cropped puffer vest (this has since sold out, shop here for a similar style) adds extra cuteness!
Turtleneck Dress and Flannel Jacket
For a cute throw-on-and-go fall transition outfit, pull on this comfy turtleneck dress. For chilly mornings, style the dress with a flannel jacket. Just add some western charm with a pair of cowboy boots, and you’re ready for brunch!
Crochet Sweater and Straight Leg Jeans
You won’t regret buying this oversized sweater! I love how the crochet knit is lightweight and literally perfect for that in-between time of year when you want a little coverage without suffocating. Pair it with some mid-rise jeans and platform sneakers for a cute and casual look.
Ruched Top and Wide-Leg Pants
I love a comfy two piece set that looks chic but feels like pajamas. Style the duo with some Adidas sneakers, a crossbody bag, and a relaxed-fit denim jacket that’s practically made for this time of year.
Trenchcoat and High-Waisted Leggings
A trench coat instantly makes even the simplest look feel elevated, which is why this combo is a cute last-minute option. Layer it over a sleek base like a fitted square neck tank and leggings. Pull on some sneakers, and you’ve got a go-to fall transition outfit when you want effortless style.
Light Wash Denim Button Down and Matching Shorts Set
Comfort meets style with this cute denim set. The oversized denim shirt tucked into the matching drawstring denim shorts—both in a gorgeous light wash—which pair effortlessly with the rich brown tones of this faux leather bag and knee-high boots.
Quilted Shacket and Sweatpants Set
This two-piece set seriously ticks all the boxes. It’s cute, comfy, and the quilted design gives it a more elevated touch than regular sweats. Styled with a cropped cami and some New Balances, it’s a quick and easy fall transition outfit that feels more intentional.
Fleece Vest and Biker Shorts
When you want to wear a cute and easy summer to fall outfit, start by opting for a pair of biker shorts and a crisp white crop tee. Dress up this sleek layer by wearing a checkered sherpa zip-up vest, a pair of your fave sneakers, and grabbing a super cute shoulder bag—because who doesn’t love a cherry keychain for a pop of fun?
Cable-Knit Lounge Set and Sweater
An oversized cable-knit sweater with matching shorts is the ultimate set for lounging around the house. Style them with these designer-inspired fur slippers that are UGG quality but budget friendly, making this look cute and easy for that in between time of year.
Faux Leather Bomber Jacket and Skort
Pair some knee-high boots and a matching brown shoulder bag with a bit of edge by throwing on a sleek black skort. Layer a white crop tee under a bomber jacket for a balanced mix of casual and polish in a fall transition outfit.
How to Transition Summer Clothes to Fall
- Layer with Intention: Keep your fave white tee or ruched top in rotation by styling them with a long sleeved knit cardigan or a leather jacket for cooler evenings.
- Play with Textures: Balance out structured pieces like denim and contrast them with a light and flowy fabric like chiffon.
- Add Seasonal Accessories: Swap out your summer straw tote for a more fall leaning piece like a faux leather bag.
- Swap Out Footwear: Turn warm weather pieces like mini skirts into fall transition outfits by swapping out summer shoes like sandals for a pair of boots.
- Balance Proportions: Pair shorter hemlined bottoms with long sleeved tops to keep things chic and practical for that in between time of year.
Cute and Easy Fall Transition Outfits from Amazon
Creating the right fall transition outfit focuses on smart layering, mixing textures, and leaning on key fall pieces to keep your style fresh. These on-trend looks prove you can rotate your favorite summer to fall pieces and style them without skipping a beat.
