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Ten Summer To Fall Outfits

  • August 26, 2025
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summer to fall outfit ideas

Yesterday, the weather dipped below 70 during the daylight hours so it’s basically fall now, right? I know, I know, don’t rush summer or whatever, but as a fall girlie to the core, I can’t resist sharing some summer to fall outfits you can wear right now. Fashion girlies love this time of year. It’s a time where we get to mix and match our warm weather clothes with our cold weather clothes. Shorts with sweaters, jackets with mini skirts, jeans with flip flops. Everything goes! These are my favorite outfits to put together because they are a bit unexpected.

Typically for these posts, I have fun scouring the internet for the cutest pieces, but for this one, I used only pieces I own. Several of them are my latest fall finds you might have seen in this post. These are all outfits I plan to wear over the next few weeks as the summer officially comes to an end.


Summer To Fall Outfits

summer to fall outfit idea with a cream tee, brown sweater over the shoulders, medium wash straight denim, red ballet flats, and a brown suede bag
tee (I sized up 2 sizes) / Sweater / jeans / bag / flats / sunglasses / earrings

If you live somewhere hot and humid like me, chances are jeans were off the table for the past three months. Well, it’s time to welcome them back! This look is a basic jeans and tee outfit, but I added in some cute red ballet flats, a faux suede slouchy bag, and a brown sweater over my shoulders. All those extras make this outfit feel a little more like autumn.


summer to fall transitional outfit with a striped tank, black barrel leg jeans, mesh ballet flats, a croco print sling bag, sunglasses, and silver hoop earrings
tank (mine is an older version) / jeans / flats / bag (ASHLEYR15 for 15% off) / sunglasses / earrings (ASHLEYROHR10 for 10% off)

I love the look of a tank top with pants or jeans, and I don’t get to wear it that often because usually the weather doesn’t allow for it. Now is the time, friends! For this look, I paired my striped tank (mine is older version from the same brand,) jeans again (barrel leg ones this time!), mesh flats, and a textured sling bag. For the morning, I would add a navy sweater over the shoulders for extra warmth.


summer to fall outfit idea with a white tee, tan barn jacket, black mini skirt, faux suede brown slouchy tote bag, and python print ballet flats
tee (I went up 2 sizes) / barn jacket / skirt / flats (check the sizing chart!) / bag / earrings

This look was inspired by my outfit I’m wearing today. This look is definitely unexpected, but I’ve seen it on some of my favorite fashion influencers, and I couldn’t wait to copy it. The oversized barn coat hangs nicely over the mini skirt here almost to the same length; it just wouldn’t look the same with a longer length skirt. I added some animal print flats, that faux suede bag (you’ll see it in a few outfits here; it’s super affordable, too!), and chunky knot earrings.


shirt / cardigan / jeans (I took my larger size) / loafers / earrings / bag (ASHLEYR15 for 15% off)

I love that this look pairs some lighter tones with some dark autumnal tones. The suede shoes and leather bag add texture and the cardigan over the shoulders brings some dimension. I can’t wait to recreate this one. So chic!


summer to fall outfit with a cream colored cardigan sweater, blue and white striped boxer shorts, brown leather fisherman sandals, a faux suede tote bag, gold knot earrings, and cat eye sunglasses
cardigan / boxer shorts / sandals / bag / sunglasses / earrings

Don’t put away those boxer shorts just yet! Pairing them with a sweater (cotton or lightweight cashmere) makes them fall friendly. I styled this look with some fisherman sandals, but it would look equally cute with a pair of ballet flats or Mary Janes.


summer to fall outfit idea with a denim button down shirt, medium wash straight leg jeans, brown leather flip flops, a green and white neck scarf, and a brow woven tote bag
shirt / jeans / flip flops / scarf / bag (mine is old from madewell) / earrings (ASHLEYROHR10 for 10% off)

Denim on denim always feels very fall to me, but for this transitional look, I kept it a little summery by pairing it with flip flops. The scarf and woven bag add some interest, too. When the weather cools, swap the flip flops for loafers.


summer to fall transitional outfit with a black cardigan sweater, white maxi skirt, mesh ballet flats, brown leather clutch bag, cat eye sunglasses, and silver hoop earrings
cardigan / skirt (mine is this one) / flats / bag (ashleyr15 for 15% off) / sunglasses / earrings (ASHLEYROHR10 for 10% off)

Another piece you can transition from summer to fall is a white maxi skirt. Pairing it with darker colors gives it more fall vibes. I went with a full on contrasting look here pairing it with black, but a dark brown or even burgundy sweater would look so cute, too.


summer to fall outfit idea with a navy sweater, light wash denim shorts, Adidas sambas sneakers and ruffle crew socks, and a Polo Ralph Lauren baseball cap
sweater / shorts / sneakers / socks (mine are similar but sold out) / bag (mine is old from Madewell) / baseball cap

Here’s your summer to fall look for the weekend. It’s giving preppy, sporty vibes. For summer, I would have paired this with a straw tote or canvas bag, but the woven leather bag brings this look into fall. I would also wear a white tee underneath this sweater to add a pop of contrast at the neckline.


summer to fall outfit idea with a black tee, black maxi skirt, black woven ballet flats, olive green suede tote bag, gold knot earrings, and cat eye sunglasses
tee / skirt (mine is old from target; this is another affordable option) / flats (stitchandsalt10 for 10% off) / bag / sunglasses / earrings

Creating an all black look with your summery pieces makes this outfit feel more fall ready. The green suede bag and black woven flats also add the autumn vibes.


summer to fall outfit with a black vest top, green barrel pants, python print ballet flats, silver hoop earrings, and cat eye sunglasses
vest (similar) / pants / flats (check the sizing chart) / bag / sunglasses / earrings (ASHLEYROHR10 for 10% off)

Here, I’m styling my new green barrel pants from summer to fall with a vest top and animal print ballet flats. This would be a good option for a more casual workplace. These pants are so versatile; look for a styling post soon!


I hope this post gave you some outfit ideas to wear right now or some tips to transition your summer outfits to fall when the weather starts cooling in your city.

Read More:
Fall 2025 Trends I’m Shopping
Copy Her Style: Katie Holmes

This blog post contains affiliate links. When you shop my links, I make a small commission at no cost to you. This is how I earn an income to support my family. Thank you!

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