warm fall outfits

30 Cute + Stylish Fall Outfits for Warm Weather

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If fall is your favorite season, I’m with you! It’s the best time of year! And I’m always ready for sweater weather before the temperatures in Virginia have consistently cooled off. In Virginia in the early days of fall, we have cool morning temps of 65 and afternoons that could be 20 degrees warmer. For 5 years, I walked a mile from my car to my office and mastered the art of early fall dressing. It’s all about having lightweight layers with dresses, pants, or jeans, and sockless shoes. A light coat, vest, or lightweight sweater is perfect in the morning. As the day warms up, you can take off your outer layer and be comfortable.

What do you wear in warm weather in the fall?

In the warm weather in the fall, pair fall colors like shades of black, orange, burgundy, yellow, olive, and brown with jeans, pants, a skirt, or shorts. Wear layers in the cooler mornings like a denim jacket, blazer, sweater, trench coat, or light utility jacket. For shoes, sockless shoes work great. Ballet flats, loafers, mules, sneakers, and espadrilles are all great options for keeping your feet warm on cool mornings and comfortable as the day warms. 

In this post, I’ll show you 30 cute fall outfits to inspire your fall wardrobe when the days are still a bit warm. Ready to dive in? Let’s go!

Dress Outfits

Let’s look at some fall outfit ideas with dresses. Some of my favorite looks for fall repurpose my summer dresses as the weather cools.

1. A t-shirt dress with an oversized shirt and sneakers

A t-shirt dress is a warmer weather staple that’s easy to wear. Pair it with your favorite fall plaid flannel shirt and as the day warms, take the shirt off and wrap it around your waist. 

A t-shirt dress with an oversized shirt and sneakers

Similar Dress | Sneakers

2. A floral dress with a denim jacket and ankle booties

You may wonder if your short floral dress can work in the fall. This dress has fall navy and orange colors. It’s perfect with a denim jacket and some booties.

A floral dress with a denim jacket and ankle booties

Denim Jacket

You have a super cute outfit even if you live in a warmer climate during the fall. 

3. A shirt dress with a short sweater and espadrilles

This short-sleeve cotton blend dress is one of my favorite dresses from summer. Here, I’m repurposing it for a fall warmer day by pairing it with a gorgeous J.Crew Chanel-inspired lady sweater. These black espadrilles are my latest crush for fall. The black suede, black ribbons, and tan woven upper are gorgeous together.

A shirt dress with a short sweater and espadrilles

Sweater | Dress | Shoes | Bag

When the morning is cool, this sweater will be one of my favorite ways to wear this dress. When the day warms, just throw the sweater over your shoulders and you still have a good-looking outfit.  

4. A midi striped wrap dress with a denim jacket and white sneakers

This short-sleeve striped wrap dress is another one that translates for fall with a short denim jacket and white sneakers. Notice that I’m wearing a classically fitted denim jacket and not an oversized denim jacket here. Since the dress has a full skirt, you want the jacket to be fitted and hit the top of the hips to keep the outfit proportions flattering.

A midi striped wrap dress with a denim jacket and white sneakers

Denim Jacket | Sneakers | Similar Bag | Similar Bag

5. A t-shirt dress with a double-breasted blazer and cap-toe flats

There are so many different ways you can breathe new life into a knee-length simple black t-shirt dress. Here I’m belting it and adding a double-breasted blazer and cap-toe flats for a work look. 

A t-shirt dress with a double-breasted blazer and cap-toe flats

Similar Dress | Blazer | Bag | Similar Cap-Toe Flats

6. A t-shirt dress with a quilted coat and brown knee-high boots

Here’s an entirely different look with that same dress. This quilted olive green barn jacket is one of my favorite fall jackets. It’s not too heavy and not too light. Add a brown belt over the dress and brown flat leather boots and you have a look that’s perfect for fall. The olive green is an earthy fall color that always works. 

A t-shirt dress with a quilted coat and brown knee-high boots

Similar Dress  | Similar Coat | Belt | Boots (old)

7. A t-shirt dress with a denim jacket and ankle boots

When you think of the perfect outer layer with a black t-shirt dress, a denim jacket probably comes to mind first. It’s the perfect length since it hits at the high hip and it’s the perfect weight for fall. I belted the dress with the same belt from the last look. For this look, I’m wearing tan ankle boots. Choose boots that match your skin tone when you’re wearing a dress and you make your legs look nice and long. Notice how these boots also hug the slimmest part of my ankle for a flattering look. 

A t-shirt dress with a denim jacket and ankle boots

Jacket | Similar Dress  | Belt | Bag | Boots (Sold Out)

8. A t-shirt dress with a duster cardigan and cap-toe flats

Here’s that t-shirt dress again. I want you to see how it works with a duster cardigan. I belted it to define the waistline. But the focal point of this outfit becomes the column of black dress that peeks out from the sweater. That draws your eye up and down and creates a very slimming silhouette. Notice how this cardigan has a straight neckline rather than a v-neck neckline. It easily hangs straight down and open.

A t-shirt dress with a duster cardigan and cap-toe flats

Similar Sweater | Similar Dress | Similar Belt | Similar Cap-Toe Flats

Pants + Jeans Outfits

With the change of seasons, I always feel happy to be able to get back into jeans and pants. Let’s look at some jeans and pants looks!

9. Black kick crop pants, a white tee, a short striped sweater, and black espadrilles

I love this look so much, I couldn’t help but recreate it with pants. These are kick crop flared pants from J.Crew Factory but you can also wear cropped wide-leg pants or any black pants really. I’m wearing a short white t-shirt under the sweater. When it gets warmer, I’ll take off the sweater and throw it over my shoulders.

Black wide-leg pants, a white tee, a short striped sweater, and black espadrilles

Sweater | Pants | Shoes | Bag

These pants are the perfect length to let those cute espadrilles peek out from under the hem. 

10. Kick crop jeans, a striped button-down shirt, a sleeveless vest, and black espadrilles

A pumpkin-colored sweater is the perfect addition to a fall wardrobe.  Here I’m wearing a lightweight vest with a striped button-down shirt. Espadrilles have an easy laid-back look that I just love and they add a feminine touch to an outfit that’s very menswear inspired. This look comes together as a laid-back preppy look.

Kick crop jeans, a striped button-down shirt, a sleeveless vest, and black espadrilles

Shirt | Vest | Jeans (regular length, fits TTS) | Shoes | Bag

11. Straight jeans with a button-down shirt, ballet flats, and a trench coat

A trench coat is a perfect option as a lightweight coat in transitional weather. This is a simple outfit of jeans and a button-down shirt. But add these Chanel-inspired ballet flats and a trench coat and you have a sharp look.

Straight jeans with a button-down shirt, ballet flats, and a trench coat

Similar Shirt | Jeans | Trench Coat | Similar Cap-Toe Flats

The cap-toe flats are a great option since they draw the eye to the end of the foot and become the focal point of the outfit when the coat is removed. As long as the temperatures are above 45 degrees, I’m comfortable wearing shoes without socks. 

12. Black kick crop pants with a sleeveless vest and black espadrilles

This pumpkin-colored sweater vest is one of my favorite autumn colors. I’m wearing it with those black cropped pants again and espadrilles. Sleeveless sweaters are so versatile since you can wear them alone or with a button-up blouse underneath. 

Black wide-leg pants with a sleeveless vest and black espadrilles

Vest | Pants | Shoes | Bag

In the morning, wear a black trench coat over top for additional warmth. 

13. Kick crop jeans with a white button-down shirt, black sweater vest, and black espadrilles

I made a beeline for this sweater vest in the store. She’s made of a heavier fabric and I’m helping her find her true calling by wearing her layered over a button-down. ⁠If you wear simple outfits, textured chunky knits elevate your look. ⁠But what really makes this look is the finer details. I’m intentionally layering in accessories with gold. The bag with gold hardware. The belt with the gold buckle. And the gold necklace, earrings, and watch. Then the black espadrilles finish the look in an easy-breezy way. 

Kick crop jeans with a white button-down shirt, black sweater vest, and black espadrilles

Similar Shirt | Vest | Jeans (regular length, fits TTS) |Shoes | Bag | Belt

14. Straight jeans with a striped button-down shirt, a puffer vest, and loafers

A puffer vest is a great way to top off your outfit when you’re walking outdoors in the fall season because your body core temperature stays warm but your arms are uncovered so you don’t overheat. This navy striped button-down shirt is one I wear every season of the year. The stripes create visual interest and the collared shirt is tailored. Wear it with a pair of jeans to work on casual Fridays. Add a belt so the look is even more formal. 

Straight jeans with a striped button-down shirt, a puffer vest, and loafers

Shirt | Jeans | Loafers | Bag | Puffer Vest

15. Black sweatpants with a white tee, green track jacket, and New Balance sneakers

This Kelly green color gives you a shot of Dopamine for sure. It’s so good. And put it in a track jacket and I’m totally in love. 

Wear this to the ball fields with your kids and peel off the jacket if the sun gets warm. These black New Balance sneakers are having a resurgence and I’m here for it. Nostalgic sneakers are a key part of my personal style. Yes, my dad wore a pair when I was a kid. Turns out he was on to something. I love the nostalgia of wearing them too.

Black sweatpants with a white tee, green track jacket, and New Balance sneakers

Jacket | Sweatpants | Sneakers | Belt Bag

16. Straight jeans with a white button-down shirt, a puffer vest, and mules

Mules or clogs are some of my favorite shoes to wear on warm fall days. They’re perfect for temperate days since they have a closed toe to keep your toes warm and an open back in case it gets really warm. This olive green puffer vest is full of fall vibes and these brown accessories are a classic color for fall. 

Straight jeans with a white button-down shirt, a puffer vest, and mules

Similar Shirt | Jeans | Mules

17. Straight jeans with a t-shirt, duster cardigan, and white sneakers

Here’s another simple look with jeans, a t-shirt, and white sneakers. This cozy sweater is comfy and warm and elevates the whole look. Wear this to watch your kids play sports or to run around town and do errands.

Straight jeans with a t-shirt, duster cardigan, and white sneakers

Similar Sweater | Jeans | Belt Bag | Sneakers

18. Black ankle pants, a white button-down shirt, a duster cardigan, and ballet flats. 

Here’s a perfect easy work look. Combine your black ankle pants with a button-down shirt, ballet flats, and a long cardigan. The cardigan is the outfit’s focal point until you don’t need it and take it off. Then the Chanel-inspired cap-toe flats steal the show. 

Black ankle pants, a white button-down shirt, a duster cardigan, and ballet flats.

Similar Shirt | Similar Cap-Toe Flats | Similar Sweater | Bag

19. A black T-shirt, black pants, and a brown leather jacket 

I’m crushing hard on this color combination. Create an all-black base and then add a brown leather jacket that’s perfect for fall. The brown platform heels happen to be a perfect match for the leather jacket. 

A black T-shirt, black pants, and a brown leather jacket

Pants

20. Cropped wide-leg jeans with a white tee, white blazer, and mules

You don’t have to skip your white blazer just because it’s fall. Here’s a very simple outfit with a white tee, a pair of jeans, a white blazer, and mules. 

Cropped wide-leg jeans with a white tee, white blazer, and mules

Blazer | Jeans (Sold Out) | Mules

21. Cropped wide-leg jeans with a gray sweatshirt, white sneakers, and a belt bag

Just like you don’t need to skip your white blazer, you don’t need to skip your white jeans, even if it’s after Labor Day. Pair your gray sweatshirt and white sneakers with your white jeans for a sporty vibe. 

Cropped wide-leg jeans with a gray sweatshirt, white sneakers, and a belt bag

Sweatshirt | Jeans | Sneakers | Bag

Next, let’s look at shorts and skirt outfits!

Shorts + Skirt Outfits

Shorts and skirts definitely work for warmer fall weather. Especially for people in warm climates.

22. A black short-sleeve sweater, black shorts, and black espadrilles

You’ve seen this sweater up above layered over a white long-sleeve button-down shirt. It’s a chunky and well-textured sweater. Add gold accessories with a gold belt and a bag with gold accents and these espadrilles make a simple outfit look expensive and elevated. 

A black short-sleeve sweater, black shorts, and black espadrilles

Vest | Shorts | Shoes | Bag | Belt

23. A white tee, white sweater, denim midi skirt, and leather flip flops

Here’s a simple layered look with your denim skirt. Throw a white sweater over top of a white tee. Give it a front tuck to define your waistline. Grab your leather flip-flops for a laid-back vibe and your straw-woven tote and you’re good to go!

A white tee, white sweater, denim midi skirt, and leather flip flops

Sweater | Skirt | Flip Flops

24. A white tee, green track jacket, white shorts, and white sneakers

Here’s that Kelly green jacket again but this time paired with white cut-off shorts and my white Tretorn sneakers with a green logo on the side. What can I say, I love a little matchy-matchy moment between my sneakers and my jacket.

A white tee, green track jacket, white shorts, and white sneakers

Jacket | Shorts | Sneakers | Belt Bag

So sporty and fresh looking!

25. A white tee, black double-breasted blazer, denim midi skirt, and cap-toe flats

Here’s a look you can wear to work if your workplace allows denim skirts. Throw your double-breasted blazer over top of a white tee and your denim skirt. These black Chanel-inspired cap-toe flats elevate the look. 

A white tee, black double-breasted blazer, denim midi skirt, and cap-toe flats

Skirt | Tank Top | Blazer | Bag | Similar Flats

26. A gray sweatshirt, black shorts, and black Adidas tennis shoes

Such a simple look that you can wear on Saturdays to the ballfield when there’s just a touch of nip in the air. If it’s much cooler, swap the sweatshirt out for a new fall chunky sweater.

A gray sweatshirt, black shorts, and black Adidas tennis shoes

Shorts | Sweatshirt | AdidasBelt Bag

27. A white tank top or tee shirt, denim midi skirt, gray sweatshirt, and white sneakers

Pair a white top with a denim skirt and throw a gray sweatshirt over your shoulders, add white sneakers and you’re ready for the day. 

A white tank top or tee shirt, denim midi skirt, gray sweatshirt, and white sneakers

Skirt | Tank Top | Belt Bag | Sneakers | Similar Sweatshirt

28. A striped boatneck top, black slip skirt, and black patent leather loafers

A striped shirt becomes the focal point and an elevating feature of an outfit. Pair it with a simple black skirt and patent leather loafers. The shine of the patent leather draws the eye in and adds another layer of visual interest. 

A striped boatneck top, black slip skirt, and black patent leather loafers

Skirt | Top | Bag | Shoes

29. A gray crewneck cardigan sweater, black slip skirt, and ballet flats

This outfit has a simple elegance to it thanks to the blush barely pink ballet flats and this gray lightweight sweater that’s buttoned up like a shirt.

A gray crewneck cardigan sweater, black slip skirt, and ballet flats

Similar Sweater | Skirt | Bag | Shoes

30. A black mock-neck sweater, black slip skirt, leather jacket, and black Adidas

You know I can’t resist this color palette of cognac brown over a black base. I love this fall look! The black Adidas gives the outfit a fresh and sporty feel. 

A black mock-neck sweater, black slip skirt, leather jacket, and black Adidas

Skirt | Top | Bag | Shoes

Getting dressed for warm fall weather doesn’t mean you can’t wear your sweaters and boots. Plan an outfit that’s layered and remove the sweater as the day warms up. Wear your ankle boots with bare legs and a skirt and a short sleeve top to stay cool as the day gets hotter.  

Infographic warm fall outfits

Hi, Friend. I'm Marya. I'm so glad you're here!

I’m here to help women feel good inside and out through approachable everyday style inspiration and encouragement for midlife. Once upon a time, I worked as a therapist and coach. Now, I’m a holistic style blogger studying style coaching! Be So You celebrates leaning into who we were meant to be! 

Read about my  journey to self-discovery at 40. Follow me on Instagram here and Pinterest here. Send me a quick question through my contact page here.  

Fit Note: I’m midsized at 5’6″, 160 pounds, with size 12 jeans.

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