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25 Summer to Fall Transition Outfits

Summer is coming to an end, and soon we’ll feel that sweet transition into fall. The crisp air. The changing leaves. Brimming holiday excitement. This time of year is one of my favorites. Not just for the things listed (and all the seasonal Starbucks drinks), but for fall fashion! That being said, the transition from summer to fall can pose a styling challenge. 

Often, especially around here, you’ll be cranking up the heat in the morning, but blasting the AC in the afternoon. So, what do you wear? Boots, jackets, and fashionable scarves are great ways to transform your warm-weather outfits into fashionable fall ensembles. But, to help you further with your autumn closet curation, I’ve styled 25 fall outfits that anyone can rock! Check it out:

25 Summer to Fall Transition Outfits

Graphic Tee and Cropped Utility Jacket

Graphic Tee and Cropped Utility Jacket

A graphic tee, shorts, and sunglasses screams summer outfit, but add a jacket and you’re ready for those chilly fall mornings and evenings! For this look, grab any loose fitting graphic tee (classic band tees work great) and black biker shorts.

Then, layer a utility jacket over top, and add your favorite quality white sneaker. Accessorize with a Saint Laurent black backpack and you are ready for a variety of temperatures! (You could even swap out the biker shorts for leggings if it’s a little cooler.)

Quilted Jacket and Black Leggings Set

Jackets are one of those key pieces of fall fashion that transform any summer outfit into an autumn outfit. They can be removed easily when it gets too warm, but they’ll keep you comfortable on a breezy or rainy day. This whole outfit is based on the gorgeous Isabel Marant Étoile quilted jacket. It has a rich, plush texture and bold seasonal colors, but it’s not too thick. (Here’s another quilted jacket option, too, if that one is sold out in your size!) 

Since this jacket has so much shape and vibrance, pair it with black leggings set. A crop top works great with this jacket because it gives you coverage while creating a flattering silhouette. Finish it off with gold jewelry and Chloé sandals in Obscure Purple or other complimentary color. It’s still slip-ons weather, y’all!

Cut Out Trench Coat Dress and Silk Scarf

25 Summer to Fall Transition Outfits

Trench coats have been a fall staple for over a century. This outfit is the perfect spin on a trench coat that serves both the summer and autumn season. First, you need the Lioness single breasted cutout trench coat dress. It’s a classic tie-front trench coat style with sexy cutouts, and you rock it as a dress! No pants required. (Though, you could grab some knit tights for more coverage and warmth.)

Underneath, add this tonal and textural cropped tank. Next, accessorize with the Tory Burch silk scarf. There are tons of ways to don a silk scarf like this. It’s such a versatile accessory! Here’s an article on different ways to tie and wear it. Anyway, this outfit demands a statement shoe. Add some color and texture variety with these ankle strap sandals. (I go for fir green, but there are tons of shades to choose from. Do you!)

Leopard Print Cardigan and Denim Shorts

Here’s an easy one you can do with things already in your closet! If you still have your summer clothes out, take a white crop top and denim shorts, and simply add a print cardigan. Not only does the sweater warm up the outfit for cooler weather, but it also elevates the look and gives it some added visual interest. Then, all you need is a cute pair of sandals and your favorite shades!

Bodysuit and Flannel with Combat Boots

Bodysuit and Flannel with Combat Boots

What says fall like a flannel? Throw on one of these classic button-ups and instantly create a summer to fall outfit. Under the flannel, wear a black bodysuit that’s sleeveless or long-sleeved depending on the temperature. Then, you just need some straight-leg jeans that are a little distressed (or a lot if you want to go all-in on this grunge tribute!) Finish the look with combat boots and an edgy black crossbody.

Oversized Crew Sweater and Leggings

For this look, you need an oversized sweater that’ll give you all the cozy fall vibes! Then, add black high-rise leggings. The varying fits between the sweater and the leggings will elongate your legs and shape a flattering figure! Then, add a fedora, because hats are totally fall! Just go from your straw panama hats to wool or felt ones instead. Finally, decide on ankle boots or heels depending on the temperature. You’re set!

Quarter Zip and Cropped Jeans

If you haven’t realized it yet, layers are perfect for fall. For these outfit layers, we start with a thin and cozy v-neck long sleeve tee and cropped jeans. Layered on top, add this sherpa quarter zip sweatshirt. Sherpa texture contrasts beautifully with denim, but it’s definitely warm. So, if you get hot, tie that sweater around your waist for another stylish way to rock this look. Oh, and don’t forget your sneakers!

Faux Leather Tee and Pants

Summer to Fall Transition Outfits

Gimme ALL the faux leather right now. One of the biggest trends this Fall is head to toe leather. This outfit is chic but Fall-ready. Add some texture with this fabulous Anine Bing bag and a pop of color with this faux leather tee! The criss-cross waist adds another level of chic, don’t ya think?

Floral Shirt Dress and Fedora

Floral Shirt Dress and Fedora

How do you make a summer dress all for fall? Boots and a fedora for sure! This outfit is really simple, take a floral dress with brown undertones, and add dramatic chocolate and gold accents. Ankle boots, a leather tote, a wool fedora, and gold hoops will help you create the perfect transitional outfit.

Puff Sleeve Mini Dress and Western Boots

Puff Sleeve Mini Dress and Western Boots

This outfit is similar to the last, but balances neutrals differently. You can read more about how to rock neutral outfits here. Anyway, grab a summer dress in orange. (Perfect for fall or summer, AND it can function like a neutral.) Then, add the black booties and fedora. At this point, you might look a little too much like Halloween, so include gold tones too with the wrist cuff and a Tory Burch crossbody bag. Now your look is perfectly balanced and totally dramatic.

Jogger Set and Denim Jacket

Activewear is no longer just for working out. Over the years, it’s totally evolved to be fashionable and easily styled into versatile outfits. This is awesome, because workout-wear is SO comfortable for running errands or chilling at home. Needless to say, the base of this look is a jogger set! Unfortunately, the one in the post is out of stock, but this nylon jogger and crop top set is a great alternative.

To take it from activewear to stylish summer/fall fashion, add a classic denim jacket and some timeless gold jewelry. Finish off this ensemble with a leather ball cap and retro-inspired sneakers. This outfit is functional, fashionable, and ready for incoming fall weather!

Flutter Sleeve Top and Paperbag Pants

Next up, we have a workwear ensemble perfect for the transitions between seasons! The outfit consists of a flowy flutter sleeve black top and breezy paperbag pants. The white and black is dramatic, but the outfit doesn’t feel or look heavy. Instead, it’s airy and completely flattering. And, don’t forget the adorable bow strap heels. The velvety texture is totally fall-appropriate, but the open toe still remembers warmer summer days!

Linen Dress and Knee-High Boots

Summer to Fall Transition Outfits

This look is SO easy. The linen dress does a ton on its own. The waist hits just right to define your figure while the drapery creates really exciting shape. I love the luxurious texture and rich color, so I doubled down for this look by adding knee-high leather boots! You can add a little color with your accessories or keep it tonal. The choice is yours!

Terry Dress and Brimmed Hat

Terry Dress and Brimmed Hat

Sweater dresses are totally fall, but when you grab one with short sleeves or a short length, it could work for summer too! This makes it a great choice for a transitional look. Unfortunately, this one is sold out, but they have their long-sleeved version and this single sleeve alternative that’ll work just the same! (Y’all excuse me while I grab every style variant of this adorable dress.) OR how about this adorable sweater dress in chocolate brown!

For shoes, you’ll need some cute calf-high black boots. And, for accessories, grab a black tote bag, black sunglasses, and your favorite Janessa Leone black straw hat! I think it needs a little gold too in order to juxtapose these dark, matte colors and textures, so I’ve selected a necklace and a bracelet to add that bright metallic sheen this outfit is demanding.

Knit Combo Dress and Boots

Knit Combo Dress and Boots | Summer to Fall Transition Outfits

This knit combo dress was made for this list. It’s got the knit sweater texture on the outside, and the breezy blouse texture on the inside. Both show for a really cool asymmetrical look. It’s also long sleeved for fall, but with a short skirt for summer. PERFECT! Just add some black boots and a waist belt and you’ve got the perfect look.

Split Cuff Leggings and Denim Jacket

Here’s another active look! Don’t your favorite graphic tee or athletic top, and wear the split cuff leggings. The little slit really elevates these bottoms, so they’re more deluxe than the average pair of black leggings. Then, over your tee, wear the puff sleeve denim jacket. Finally, grab the sherpa sneakers! This outfit works for a variety of seasons and activities.

Wool Cardigan and Sherpa Sneakers

Wool Cardigan and Sherpa Sneakers OOTD

Don’t put those sherpa sneakers and split top leggings away. We need them for this look! Swap out the graphic tee and denim jacket for an oversized cardigan and you’ve got a look with a whole different feel. It’s trendy, preppy, and perfect for that time between summer and winter.

Flowing Floral Dress and Heels

Flowing Floral Dress and Heels

In this collage, I have a ton of print dresses to choose from. The one I’m using for this outfit, though, is the long, flowy Elliatt Astrid dress. It’s got that voluminous structure that’s perfect for summer. It’s cool and has a ton of breezy movement. But, it’s a long dress with long sleeves, so it totally works for fall too. All you need are some fall tones! Accessorize using this inspo post on hats and bags, and your look is complete.

Sweater Dress and Crocodile Boots

Sweater Dress and Crocodile Boots Outfit

Here’s another short sweater dress from Retrofête that totally works for that in-between period. It has a plunging v-neck and a mini skirt length, but it’s made of cozy knit fabrics. It comes in a few colors, so if you don’t see the size you need in this one, definitely search for more! All you need with this dress are some faux crocodile skin boots and a pendant necklace. Y’all, I am ready to bust this dress back out again!

Knit Blazer and Jeans with Heels

Knit Blazer and Jeans with Heels | Summer to Fall Transition Outfits

This knit blazer is a-maz-ing. It’s comfy like a sweater, but it feels totally professional. Pair this with a fun print blouse or a solid tee. Then, rock the high waisted jeans with the wide leg. The blazer shoulders and the wide cuffs combined with the cinched waist will give you a gorgeous hourglass figure. Finally, put on the knotted sandals in a coordinating color to look ready for work or a lunch date in any season!

Puff-Sleeve Shirt and Leopard Slip Skirt

Amazon Prime Day fashion finds

There are some incredible Amazon fall finds on this post, but for this outfit, grab that black puff-sleeve crewneck and the leopard slip skirt. It combines heavy and light textures as well as simple and bold prints. It’s exciting, so easy to wear, and won’t look weird whatever the weather. For accessories, I’ve got you covered here. The black Jennifer bootie and Loeffler Randall cinched crossbody are perfect for this outfit!

Mint Green Blazer with Matching Handbag

Your summer to fall transitional outfit doesn’t need to be all about fall neutrals and deep wintry hues. No way! Let’s keep the summer alive with this mint green outfit! Denim shorts and a white crop top will do for the base. Then, the wild mint green blazer goes over the top.

Accessorize with a matching handbag and those black butterfly sunglasses! For shoes, you can keep it understated with a black or white sandal, or keep it fun by carrying the mint color all the way down.

Linen Blouse and Cotton Trousers with Gold Jewelry

Linen Blouse and Cotton Trousers

For this outfit, you’ll take a linen tie-front top that’s breezy and flattering for almost any body type! Combine it with white, wide-legged cotton pants and Gucci loafers for a casual, but chic fall/summer outfit. Gold jewelry will tie in the loafer accents and elevate the outfit.

Halter Top and High Rise Jeans

Halter Top and High Rise Jeans

Here’s another simple ensemble that’s ideal for this transitional period. Simply take a black halter top and rock it with these criss-cross medium wash jeans. The geometric shapes of the neckline and waist just totally work for a trendy ensemble. Accessorize with a straw hat, black slides, and a wild print handbag (because every look needs a little adventure!)

Black Jean Jacket and Cropped Jeans

Black Jean Jacket and Cropped Jeans | Summer to Fall Transition Outfits

For my last look, grab this Program Epaulette t-shirt in black and layer over it a black jean jacket. I love the texture and vintage-look of this coat. Plus, all the angles are exciting and give you a lot of shape! Complete the look with a pair of cropped regular denim jeans and a pair of sneakers. The outfit isn’t too hot, isn’t too cold. It’s just right!

Let’s not think of the summer to fall transition as a style challenge, but let’s think of it as a style opportunity!

This season allows us to rock gorgeous jackets AND comfy mini dresses! You can wear heels or boots, hats or sunglasses, bright or dark colors—whatever you want! Anything is appropriate, because the weather is unpredictable, and we haven’t officially hit fall on the calendar. So, grab your favorite pieces from all the seasons, and combine them to create outfits with good layering. You’ll probably come up with a ton of new ideas and combinations!

If you’re looking for fall style ideas for kids and maternity, I’ve got posts on that too! Just click the links. And, don’t forget to show me your transitional outfits. Tag me on Insta, so I can see how you ran away with these style ideas. If you like this post, make sure to check back for more articles weekly on my blog!