cute fall outfits

30 Cute Fall Outfits You’ll Love to Wear for 2023

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So September is just a few days away and I can’t even believe we’re heading into the last quarter of the year! Where, oh where has the summer gone? 

The good news is that the fall season means it’s time for fall fashion! And we get to wear our favorite jeans and cozy sweaters!

In this post, I have a massive photo dump of 30 very cute outfits for casual occasions, work, or a night out. These looks will take you through the fall season! Some are made with pieces from my fall capsule wardrobe. If you haven’t seen that post yet, you can check it out here, 52 Outfits + The Ultimate Fall Capsule Wardrobe 2023. There’s plenty of outfit inspiration for you here!

How do you dress fashionably in the fall?

To take your looks to the next level, create outfits that keep you warm and look stylish. Layering instantly brings visual interest to your outfits. Start with your favorite pair of jeans, wide leg trousers, a midi dress or skirt, or a chic sweater dress. Add a third piece like a blazer, sweater blazer, trench coat, long statement coat, or leather jacket. To instantly add polish, play with suede, leather, plaid, cable knit, and textured woven materials. Add your favorite boots, a scarf, a hat, and a bag and you’re sure to look fashionable.

Let’s look at some fall outfit ideas, shall we? 

Fit note: For reference, I’m 5’6″, 160 lbs, 36-B bust, and wear size 12 jeans and a small or medium top.

A striped shirt, coated jeans, and black Mary Janes

If you’re smaller up top than on the bottom like I am, wearing stripes up top and buttons on your shoulders helps to create a more proportional silhouette.

A striped top makes your outfit pop with minimal effort. Notice how this shirt is black and tan. The tan gives it a fall vibe.

Pair black stripes with any black pants you have. Here I’m wearing them with coated wide leg jeans.

A striped shirt, coated jeans, and black Mary Janes

Shirt | Pants | BeltBag | Shoes

A navy cardigan, white top, flare jeans, and brown mules

Navy is the perfect fall color. And this cable knit navy cardigan from J.Crew is a gorgeous layering piece. A column of one color is super chic so don’t be afraid to wear a navy sweater with dark jeans.

A navy cardigan, white top, flare jeans and brown mules

Sweater | Top | Jeans | Bag

Notice how cognac brown accessories bring all the fall vibes here! Navy and cognac brown are a match made in heaven.

A cardigan, printed maxi dress, and mules

Here’s another navy look with cognac brown accessories. For this look, I’m wearing a long tiered maxi dress with a short cardigan. I like to layer a short cardigan with a long skirt. The fitted sweater counteracts the flowy skirt keeping the proportions from looking frumpy.

A cardigan, printed maxi dress, and mules

Cardigan | Dress | Bag

If you’re curious about how to wear cardigans with dresses, check my post, 15 Cute Outfit Ideas to Style a Cardigan with a Dress.

A sweater dress, trench coat, and Mary Janes

A sweater dress is so chic for fall! This is my favorite Breton stripe sweater dress from the Gap. Add a trench coat over the top and some Mary Janes and you’re ready for the seasons to change.

A sweater dress, trench coat, and Mary Janes

Sweater dress (order “tall” for knee length) | Trench coat | ShoesBag

A striped cardigan, wide leg cropped jeans, and Mary Janes

This striped cardigan from J.Crew is the big winner of the fall season. I’ve styled it a million different ways. And there’s something to be said about how a quality piece makes an outfit with very little effort. I’m wearing it with my high waist wide-leg cropped jeans. It’s a short sweater that works perfectly with high-waisted jeans. 

Black Mary Jane flats, a black belt with a gold buckle, and my Coach purse finish the look. At Anthropologie, I picked up this black Paris baseball hat and it’s the cutest thing ever. It’s a great way to stay covered when you’re worried about rain showers. 

A striped cardigan, wide leg cropped jeans, and Mary Janes

Jeans (sold out) | Hat | Belt | Shoes | Sweater | Bag

A white button down, black sweater vest, kick crop jeans, and black espadrilles

A white button-down shirt is a closet staple. Here I’m layering it underneath my black sweater vest. And I’m wearing my kick crop jeans from the Gap in a regular length. I own them in two lengths and these are shorter and work great with these black espadrilles. My black belt with a gold buckle and black Coach bag tie the look together. 

A white button down, black sweater vest, kick crop jeans, and black espadrilles

Sweater Vest | Button-down Shirt | Jeans (Regular length) Belt | Shoes | Bag

A chambray shirt, coated wide-leg jeans, and silver Mary Jane flats

This look was an experiment that I ended up loving. Pair a chambray shirt with coated wide-leg jeans and silver Mary Jane flats. While it’s hard to call silver shoes a closet essential, they add a fun and unexpected twist to your look. When I wear them I always want to switch out my gold jewelry for silver jewelry but I forgot here.

A chambray shirt, coated wide-leg jeans, and silver Mary Jane flats

Shirt | Pants | Similar Shoes

A striped tee, Houndstooth blazer, kick crop jeans, and white loafers

This white and navy striped tee is so fun with this Houndstooth blazer. A Houndstooth blazer is one of those perfect fall pieces. An oversized blazer is one of the latest trends, but I always love the look of a classic blazer. I’m wearing my longer kick-crop jeans and my cream tassel loafers on the bottom. And carrying my black quilted bag. I love how this taupe baseball hat pulls out the light colors of the blazer. 

A striped tee, houndstooth blazer, kick crop jeans and white loafers

Blazer | Shirt | Jeans (Long length) | Loafers | Bag

A striped shirt, leather jacket, flare jeans, and ankle boots

Here’s another easy outfit. Throw your striped shirt on with flare jeans, a leather jacket, and matching ankle boots. Notice my black belt has a gold buckle, and my bag has gold clasps. So I’m wearing gold jewelry to match.

A striped shirt, leather jacket, flare jeans and ankle boots

Shirt | Jacket | Jeans | Similar Ankle Boots | BeltBag

A white tee, black sweater vest, black kick crop jeans, and black espadrilles

Here’s an easy outfit with a white long-sleeve tee, a black sweater vest, and black kick crop jeans, another Gap purchase. I’m tying the look together with gold accessories and a black and gold belt.

A white tee, black sweater vest, black kick crop jeans and black espadrilles

Sweater Vest | Top | Jeans | Belt | Shoes | Bag

A gray turtleneck sweater, navy maxi dress, and taupe ankle boots

Fall dresses are easy to wear. This navy Madewell maxi dress is one I got from Nordstrom Rack on sale. You can totally wear a pullover sweater with a maxi dress for a different look. It’s important to define the waistline of the outfit. To do that, I’m wearing a belt under the dress and tucking the hem of the sweater up under the belt. Pushing up your sleeves also helps. With a long dress, choose ankle boots that match your skin tone to extend the length of your legs. Tall leather boots are another great option.

A gray turtleneck sweater, navy maxi dress, and taupe ankle boots

Dress (size down) | Similar Boots | Bag | Similar Sweater

A striped button-down shirt, gray cardigan, wide-leg jeans, and Chelsea boots

Who doesn’t love layering a cardigan over anything in the fall? Here I’m layering it over my favorite striped button-down shirt. And wide-leg jeans and Chelsea boots. Wearing baggy jeans and a cardigan makes for a cozy fall outfit.

A striped button-down shirt, gray cardigan, wide-leg jeans, and Chelsea boots

Jeans | Bag | Shirt | Similar Cardigan | Boots

A cream sweater, black utility jacket, black kick crop jeans, and black New Balance sneakers

Here’s an outfit that’s perfect for the pumpkin patch. I’m wearing a short-sleeved cream sweater, black kick-crop jeans, a black utility jacket, and black New Balance sneakers. Retro sneakers are having a moment and I’m totally in love with these. They’re perfect since I wear so much black. My black Paris baseball hat would be perfect here. 

A cream sweater, black utility jacket, black kick crop jeans, and black New Balance sneakers

Jeans| Bag | Sneakers | Jacket | Similar Sweater

A black sweater vest, Houndstooth jacket, black wide-leg trousers, and black espadrilles

Wide-leg trousers are all the rage these days and they do make for a sharp outfit giving you legs that go on for days. I’m adding my Houndstooth jacket over a column of black with these black espadrilles for a work-friendly look.

A black sweater vest, houndstooth jacket, black wide-leg trousers, and black espadrilles

Similar Trousers | Blazer | Sweater Vest | Shoes | Bag

A black tiered dress, black moto leather jacket, and black Mary Jane flats

Here’s a look for date night. This tiered dress from Old Navy is one of my favorites. I love pairing it with these Mary Jane flats. Leather jackets are perfect over dresses if you want to keep a look from feeling overly sweet. It adds an edgy vibe.

A black tiered dress, black moto leather jacket, and black Mary Jane flats

Similar Dress | Jacket | Bag

You could also wear black knee-high boots here if the day is colder. There’s no better time for tall boots than in fall. 

A Breton stripe shirt, ecru cropped wide-leg jeans, a black collarless sweater blazer, and cream loafers

You don’t have to put away your white jeans after Labor Day anymore. And here’s a perfect way to wear them. Pair them with a striped shirt and add a black cardigan sweater over top. This is the Juliette collarless sweater blazer from J.Crew. It’s a weighty sweater that’s perfect on a day when you want extra warmth but prefer a sweater over a coat. These cream tassel loafers add a tailored look.

A Breton stripe shirt, ecru cropped wide-leg jeans, black collarless sweater blazer, and cream loafers

Jeans (sold out) | Shirt | Sweater | Loafers | Bag

A white tee, gray cardigan, black kick crop jeans, and black New Balance sneakers

Here’s an easy laid-back outfit. Pair your black cropped jeans with a white tee and throw a gray cardigan over top. Add black sneakers to run around all day.

A white tee, gray cardigan, black kick crop jeans, and black New Balance sneakers

Jeans | Bag | Sneakers | Similar Sweater | Tee

A black moto jacket, black maxi dress, and black Mary Jane flats

Maxi dresses are having a moment. And this one comes in a fall floral with a black background. You may think of pairing a dress with a denim jacket. And that’s always a great option. But a leather moto jacket is perfect if you don’t want your look to be too sweet. I love this leather jacket because the zipper and snaps are black rather than silver so the look isn’t quite so edgy. It feels more like me.

A black moto jacket, black maxi dress, and black Mary Jane flats

Similar Cardigan | Dress | Shoes | Bag

A chambray shirt, black sweater vest, black kick crop jeans, and Chelsea boots

Here I’m making a column of denim with a chambray shirt and blue jeans. And adding a black sweater vest. You can make this look with any color sweater vest or any color sweater over top. 

A chambray shirt, black sweater vest, black kick crop jeans and Chelsea boots

Shirt | Sweater Vest | Jeans (Long length) | Bag | Boots

A black tie-neck blouse, Houndstooth blazer, kick crop jeans, and ankle wrap pumps

These ankle wrap pumps are some of my favorites. The heel isn’t too high and they’re very wearable. I did a whole post about how to wear heels with jeans and showed a bunch of ways to wear these heels. I love pairing elevated pieces like this blouse and blazer with a casual piece like jeans.

A black tie-neck blouse, houndstooth blazer, kick crop jeans, and ankle wrap pumps

Jeans (Short length) | Heels | Bag | Belt | Similar Blouse | Blazer

Wear this to Thanksgiving or a Friendsgiving event. 

A striped button-down shirt, black girlfriend chinos, black collarless sweater blazer, and brown mules

I love combining black clothing with brown accessories for a pop of contrasting color. I match the belt, shoes, and handbag so the brown shoes make sense here. My blue and white striped button down is one of those classic staple pieces that also adds contrast. And then this collarless sweater blazer finishes the outfit for a comfy work look. 

A striped button-down shirt, black girlfriend chinos, black collarless sweater blazer, and brown mules

Cardigan | Shirt | Bag

A white sweater, blue wide-leg jeans, and black Mary Jane flats

This white sweater is a favorite find from the Nordstrom Anniversary Sale this summer. If you like simple outfits, pieces with texture add more visual interest. Wide-leg cropped jeans and those black Mary Janes make for a cute outfit. Cargo pants would also be cute here if they fit with your style.

A white sweater, blue wide-leg jeans, and black Mary Jane flats

Sweater | Jeans (sold out) | Belt | Shoes | Bag

A white button-down blouse, black coated jeans, and black Mary Janes

Who knew I would love a crisp white button down with these black coated jeans? But it works! I did a messy roll of the sleeves for a laidback look. And the black belt looks perfect here. Black Mary Janes add a playful vibe to the look.

A white button-down blouse, black coated jeans, and black Mary Janes

Belt | Shoes | Bag | Pants | Shirt

A black turtleneck sweater, black coated jeans, black trench coat, and black Mary Janes

Here’s an outfit that’s perfect for a fall rainy day, except swap the Mary Janes out for black ankle boots. I’m pairing a thin turtleneck sweater with those coated black jeans. Yes, it’s okay for them to get wet. Add a black trench coat over top and a black baseball cap. How much do I love this look? It’s one of my favorite fall outfits, and makes all my black clothing dreams come true!

A black turtleneck sweater, black coated jeans, black trench coat, and black Mary Janes

Turtleneck | Hat | Belt | Shoes | Bag | Pants | Trench Coat

A green track jacket, black sweatpants, and black New Balance sneakers

Green is one of those bright colors that we’ll be seeing a lot of this fall. And I love this sporty track jacket with a white stripe on the sleeves. I’m wearing it with my favorite black sweater and my black New Balance sneakers. White sneakers would also work here. 

A green track jacket, black sweatpants, and black New Balance sneakers

Jacket | Bag | Sweatpants | Sneakers (black/black/grey)

A striped sweater, wide leg cropped jeans, and black Mary Janes

Red is a hot color for fall. And this is the perfect sweater if you want to add just a hint of red to your wardrobe. And combine it with a black and white stripe. This lightweight 100% cotton sweater has a drop shoulder and is boxy. Oversized knit sweaters are in right now. I ordered a large and definitely could size down since I like a more streamlined fit. Love the Mary Janes with wide-leg cropped jeans!

A striped sweater, wide leg cropped jeans, and black Mary Janes

Jeans (sold out) | Sweater | Belt | Shoes

A gray turtleneck sweater, black coated jeans, and black Mary Janes

You don’t need coated jeans to make this outfit. Choose any black jeans or pants and pair them with your favorite gray sweater. Add a good-looking black belt and black shoes and you’re set.

A gray turtleneck sweater, black coated jeans, and black Mary Janes

Belt | Shoes | Bag | Pants | Similar Sweater

A striped cardigan, black moto jacket, wide leg jeans, and wedge slides

I’m a sucker for any stripes. This look has an edgy vibe by combining this striped sweater with a moto jacket and black strappy wedge sandals to carry the black through the outfit.

A striped cardigan, black moto jacket, wide leg jeans, and wedge slides

Sweater | Jacket | Jeans | Heels (go up a half size)| Bag

A black turtleneck sweater, black coated jeans, and black Mary Janes

This black turtleneck sweater was a surprise classic find from H&M. You have to be prepared to rummage through the racks but you can find some good staple pieces at affordable prices. An all-black look is super chic, especially if you’re wearing coated jeans for visual interest. Swap out the black turtleneck for a black top, if you prefer that. 

A black turtleneck sweater, black coated jeans, and black Mary Janes

Belt | Shoes | Bag | Pants | Turtleneck

A gingham button down, orange sweater vest, wide leg jeans, taupe ankle boots, and a long navy coat

This sweater vest brings on the fall colors! I’ve been seeing navy gingham button-downs in the stores and had to pull mine out and pair it with this vest for a fun fall look. I’m pairing it with these wide-leg jeans and my classic taupe ankle boots and throwing my navy long coat over top for an elevated look.

A gingham button down, orange sweater vest, wide leg jeans, taupe ankle boots, and long navy coat

Coat | Vest | Similar shirt | Jeans | Bag

Have anything fun planned for fall? Leave a comment below, I’d love to know!

infographic, cute 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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