From NYC to Europe: 12 Midsize Fall Outfits to Keep You Cozy in Style

by Ann Shortt
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As the crisp air settles in and sweaters begin to emerge from hibernation, it’s the perfect time to explore exciting fall outfit ideas! Women of all shapes and sizes deserve to feel comfortable and stylish, and with our playful collection of cute, casual options, you won’t have to sacrifice one for the other. We’ve gathered 12 fabulous fall outfits, drawing inspiration from both NYC street style and charming European fashion that’s perfect for the midsize woman.

Think of cozy oversized coats layered over sweet vintage dresses that scream effortless chic. While autumn might be about bundling up, it doesn’t mean you can’t flaunt your personal style! Early autumn is the ideal time to showcase those adorable outfits that hug in all the right places while still leaving room for a warm latte (or three!). Let’s face it, the only thing better than a cute outfit is a cute outfit with extra warmth!

Everyone loves the classic look of a denim jacket layered over a soft sweater, complemented by stylish ankle boots. It’s casual, cute, and simply unstoppable this fall! As you embrace these outfit ideas, you’ll find that it’s incredibly satisfying to mix classic vintage pieces with modern staples. With this blend, you’ll harness that effortless European flair, proving that size is no barrier to fabulous fashion!

But hold on—what about accessorizing? No outfit is complete without the right touches. Think statement scarves, fun hats, and chunky jewelry that can transform your look instantly. Fall is about layering and texture, and by adding these elements, you can make any outfit uniquely yours. It’s all about crafting your personal style story that others will be eager to hear!

Get ready to take notes because we’re about to unveil these 12 cozy fall outfits for the midsize woman in 2024. Prepare to strut your stuff and breathe confidence this autumn—with your wardrobe’s new potential, the season will be your runway! So let’s dive into this world of fall fashion and create some style magic together!

#1 Pleated Perfection: Fall Fashion Trend

Pleated Perfection: Fall Fashion Trend

The weather is getting cooler, the leaves are changing colors, and it’s time to start thinking about fall fashion. This stylish outfit is perfect for those midsize ladies who want to look chic and comfortable during the fall season. The cozy cardigan looks like it’s ready to snuggle up in, and the sleek black dress adds a touch of sophistication. It’s like having a warm hug with a side of elegance!

Think of it as a fashion equation: A little bit of comfy plus a little bit of dressy equals a whole lot of confidence. This outfit can take you from a casual coffee date to a fancy dinner party, and everywhere in between. And with the addition of some stylish accessories, you’re ready to rock the fall season in style!

#2 Pumpkin Spice & Everything Nice:

Pumpkin Spice & Everything Nice:

This outfit is proof that you don’t need to sacrifice style for comfort when the weather gets colder. Forget the baggy sweaters and oversized scarves – this girl is rocking a chic yellow coat, a leather skirt, and white booties. It’s like a fashion statement that whispers, “I’m ready for fall, but I’m not afraid to show off my personality.” She’s got the whole “cool girl” look going on, and it totally makes you want to ditch those oversized sweaters and embrace something a little more edgy.

But let’s be real, who has time to worry about being edgy all the time? Sometimes you just need a look that’s comfy, stylish, and doesn’t require a ton of effort. This outfit is perfect for that! It’s easy to throw on and still makes you feel good. And honestly, who doesn’t love a little bit of leather in the fall? It’s the perfect way to spice up your look and embrace that “fall feels” vibe. So, ditch the sweatpants and get ready to rock the fall season with a touch of midsize fashion inspiration!

#3 Stripes, Skirts, & Smiles:

Stripes, Skirts, & Smiles:

This outfit is giving us major autumn goals! That skirt is like a warm hug for your legs, and the stripes are totally on-trend. Plus, you know what they say – when in doubt, wear a classic button-down shirt! It’s the perfect combo for when you want to look put-together without trying too hard. Throw on a cozy sweater or jacket on top and you’re ready to rock the fall season, whether you’re heading to class, grabbing coffee with friends, or just chilling at home. Don’t forget to add your own personal touch with some cute accessories – maybe a scarf or a fun hat!

The best part about this look is that it’s super versatile. You can dress it up with heels and a blazer for a fancier occasion, or keep it casual with sneakers and a denim jacket. Whatever your style, this outfit is sure to keep you looking and feeling amazing all fall long!

#4 Ready For Anything: The Midsize Dress

Ready For Anything:  The Midsize Dress

This dress is like the MVP of your fall wardrobe – it’s sleek, stylish, and perfect for everything from a casual coffee date to a fancy dinner. And the best part? It’s not too tight, not too loose, it’s just right! Think of it like that comfy pair of jeans you live in, but dressed up in a super cute dress version. This dress is all about feeling confident and amazing, no matter what the day throws at you. Plus, with those cute white booties, you’ll be ready to strut your stuff with a smile on your face!

So ditch the jeans for a day and give this dress a chance. You’ll be surprised how good you feel when you’re rocking a look that’s both stylish and comfy, because honestly, who wants to be uncomfortable when the leaves are changing and the weather’s getting cooler? Let’s embrace this fall season with outfits that make us feel like we can take on the world, one perfect dress at a time. 😉

#5 Layer Up & Shine: Fall Style Guide

Layer Up & Shine: Fall Style Guide

This outfit screams “I’m ready for fall” without even saying a word! The pink skirt is totally on-trend and the white sweater keeps you cozy when the weather gets chilly. And let’s not forget those awesome shoes! They add a little bit of edge and make the whole look super stylish. You can totally rock this outfit for a day of school, a trip to the mall, or even a night out with friends!

This outfit is like the perfect balance between being comfy and cute. It’s the kind of outfit that makes you feel confident and ready to take on anything, which is exactly what we all need when the leaves start changing colors! You can always add some accessories, like a cute scarf or a funky hat, to make it even more your own. Don’t be afraid to experiment and find what makes you feel amazing!

#6 Stripes, Vests, & Joy:

Stripes, Vests, & Joy:

This outfit is like a warm hug on a chilly day! The girl is rocking a comfy grey turtleneck, a flowy printed skirt, and some seriously cool white sneakers. It’s the perfect way to look put-together and comfy at the same time. Imagine walking through crunchy leaves in this outfit, maybe grabbing a pumpkin spice latte, and feeling like the most stylish person in town! It’s the kind of outfit that makes you feel confident and ready to tackle anything fall throws your way.

But let’s be honest, it’s not just about the clothes, right? It’s about the feeling! It’s about feeling cozy and stylish and ready to embrace all the fun of fall. So grab your favorite turtleneck, find a skirt that makes you feel amazing, and rock those sneakers! This is the perfect outfit to show off your midsize style this fall!

#7 Turtleneck, Skirt, and Power:

Turtleneck, Skirt, and Power:

This outfit is like a high school hallway, but instead of locker slams, it’s filled with style. The classic black turtleneck is your go-to friend, the blue skirt is the new kid everyone wants to be friends with, and those boots are the star athlete who’s always confident. And hey, you don’t need a uniform to look awesome – this look is all about feeling good and owning your style!

Who says fall can’t be stylish? This outfit is proof that you can stay comfy and look amazing at the same time. Plus, the colors are perfect for the changing leaves – the black and blue blend in so you can blend right in, but the sleekness of the whole look will make you stand out from the crowd! So, ditch the sweatpants, grab your favorite boots, and rock that fall fashion!

#8 The Midsize Must-Have: Fall Edition

The Midsize Must-Have: Fall Edition

This outfit is perfect for someone who wants to be stylish and comfortable at the same time! It’s got a great balance of casual and cute, kind of like a pizza with just the right amount of toppings! The striped dress is totally classic, like a good pair of jeans, and the vest adds a little bit of “I’m not afraid to be different” vibes. And let’s be honest, who doesn’t love a good vest? They’re like the cool jackets of the sweater world!

Let’s talk about the smile. Seriously, how can you not be happy in this outfit? It’s like it’s got a built-in sunshine feature! This outfit is totally ready for fall adventures, like pumpkin picking or maybe a trip to the apple orchard. Just picture it – you’re surrounded by gorgeous fall colors, and you’re rocking this cool, comfy outfit. It’s a recipe for an awesome autumn!

#9 Fall Fashion: Pleats, Please!

Fall Fashion:  Pleats, Please!

This outfit is giving major “fall vibes” with that gorgeous rust-colored pleated skirt! It’s like the leaves outside decided to make an outfit – and they look amazing. The white top and sparkly jewelry add a touch of elegance, making this outfit perfect for anything from a casual date night to a fancy school event. Plus, who doesn’t love a skirt that flows like it’s dancing in the wind?

And let’s talk about those shoes! They’re like a perfect match for the skirt, and they’ll definitely give you that confident strut down the hallways. This outfit is all about embracing the season’s colors and feeling good about yourself, so get out there and show off your style!

#10 Midsize Muse: Fall Outfit Inspiration

Midsize Muse: Fall Outfit Inspiration

This outfit is giving us major fall vibes! It’s all about that comfy, cute, and stylish look that’s perfect for those chilly days. The blush-colored top is a must-have, and the dark blue skirt adds a touch of sophistication. And let’s be real, those white boots are everything! Who needs a pumpkin spice latte when you’ve got an outfit this good?

It’s all about feeling confident and stylish, no matter your size! This outfit proves that you can rock anything with a smile on your face. Imagine yourself strolling through the park in this look, maybe grabbing a pumpkin spice latte (because, hey, why not?), and feeling like a total fashion queen! You’ve got this, girl! 😉

#11 Fall Fashion Upgrade:

Fall Fashion Upgrade:

This outfit is perfect for anyone looking to add a touch of sophistication to their fall wardrobe. The classic black dress is a staple for any occasion, and the creamy white jacket adds a touch of warmth and elegance. The outfit is pulled together with a stylish brown belt and matching clutch. Plus, those heels are totally rocking! This is a look that’s sure to turn heads, whether you’re heading to a school dance or a fancy dinner with your fam.

But seriously, imagine walking into school looking like this. All eyes would be on you! It’s the kind of outfit that makes you feel like you can conquer anything. Just remember, confidence is the best accessory, and this outfit is sure to give you an extra boost of it! So go ahead, embrace your inner fashionista and get ready to shine this fall!

#12 Fall’s Skirt Story:

Fall's Skirt Story:

This outfit is giving “I woke up like this, but better” vibes! It’s the perfect mix of comfy and chic. That cozy sweater is begging for a hot cup of cocoa and a good book by the fireplace, but that skirt screams “business meeting” or “killer date night!” This look is proof that you can be both comfy and put-together, and it’s totally achievable for anyone, no matter their size.

Think about it: You can swap the skirt for jeans, a cute dress, or even a jumpsuit! The possibilities are endless when it comes to creating your own midsize fall fashion masterpiece. So ditch the oversized sweatshirts and sweatpants! Embrace the season’s trends with this adorable outfit, and let your confidence shine!

#13 Midsize Style: Chic & Confident

Midsize Style: Chic & Confident

This outfit is totally giving us “fall vibes” without sacrificing any style! The black turtleneck sweater and teal skirt is a combo that screams sophistication, while the black tights and heels add a touch of elegance that’s perfect for those cool autumn days. We can definitely picture ourselves strolling through a pumpkin patch or grabbing coffee with friends in this look – it’s comfy, stylish, and ready for anything!

Don’t let the chilly weather steal your fashion thunder! Mix and match with different colors and textures to find the perfect combination for you. Whether you prefer a more casual or dressed-up look, remember that there’s no wrong way to rock fall fashion! Just remember to layer up for the cooler weather, and keep those fashionista vibes strong!

#14 Camel Chic: Fall’s Luxe Look

Camel Chic: Fall's Luxe Look

This outfit is like a warm hug on a chilly fall day! That camel coat is totally classic, and it looks super comfy. It’s like a cozy blanket you can wear out and about. And those shoes! They’re the perfect match for the coat, they’re both classy and stylish, but also easy to walk in. You could wear this outfit to school, to a date, or even to a fancy dinner, and you’d look absolutely amazing!

So, if you’re looking for a fall outfit that’s both trendy and practical, you might want to consider something like this. Who knows, you might even find your own camel coat love story! Just make sure to get the right size, otherwise, you might end up looking like you’re wearing your mom’s coat, and that’s never a good look! 😉

#15 Own Your Style: Midsize Fall Fashion

Own Your Style: Midsize Fall Fashion

Forget pumpkin spice lattes and oversized sweaters! Fall fashion is all about finding that perfect skirt. This girl in the picture knows what’s up! She’s rocking a killer blue skirt with a yellow top that’s totally on-trend. It’s the kind of outfit that makes you feel confident and ready to take on the world, or at least the school cafeteria. Just remember, a great skirt is like a good friend – always there to make you feel fabulous!

With the changing leaves comes a chance to revamp your wardrobe. This fall, think about ditching the sweatpants and embracing the amazing world of skirts! They’re comfy, they’re stylish, and they come in a million different styles. So grab your best skirt and get ready to rock the season, just like this fashion-forward queen!

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