Dressing for the Season: Chill Fall Fits That Feel as Good as They Look

Are you the type who trades comfort for style? 

I’m sure you don’t fancy chilling your bones while trying to slay the fresh fall trend. While the major focus of us women is on looking cute and riding the new fashion wave, a cozy fall outfit can keep you comfy without sacrificing style. 

Chill fall fits that are centered around comfort are all about fusing cozy and chic. Here are some of the cozy looks that definitely keep you warm but also elevate your autumn aesthetic. The type of style that not only turns heads but also nestles you in a warmth—equal part lazy-day cozy and effortlessly stylish. 

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Cozy Fall Outfits That Look and Feel Amazing 

Cozy Fall Outfits That Look and Feel Amazing 

behrouz sasani on Unsplash 

1. Oversized Sweater and Leggings

The one look that keeps it 100 on the comfy scale is the oversized sweater and leggings look. A perfect pair that gives you that stay-in-it-all-day comfy feel while making you look effortlessly chic. 

You can layer this pair with anything, throw on a statement scarf, chunky boots, or even a cute beanie, and you’ve got an instant cozy fall outfit. No trade-off is needed—this look nails both comfort and style. 

ANINE BING
Cole Legging

BLOOMINGDALE’S | HUE
Wide Waistband Leggings

2. Cozy Knit Dresses

Knit dresses are all the rage this fall, with people dressing them up in style with ankle boots and a cute scarf or keeping it low-key with chunky sneakers and oversized jackets. Either way, you’re serving a look with minimal effort. Got a date, casual brunch, or even just a coffee run? They add a touch of sophistication while still maintaining a relaxed vibe. 

MARIE OLIVER
Halsey Dress

MARIE OLIVER
Misha Dress

Shackets are the Cozy Fall Outfits That Look and Feel Amazing 

hossein beygi on Unsplash 

3. Shackets for Easy Layering 

When the weather can’t decide what it’s doing, too chili for a shirt but too warm to bundle up with a full-on coat, shackets are your ultimate savior. A stylish love child of a shirt and a jacket.  

This hybrid between a shirt and a jacket is all about ease and style, making them the reliable option for those crisp autumn days. In those weird in-between weather, a shackets with its relaxed fit and easy laying can give you a snug comfort without feeling heavy, so you can stay cozy while still looking on point. 

What’s more, they come in all kinds of styles—from plaid prints that shout out the autumn vibe to sleek neutrals that can match up with almost anything in your fall wardrobe.

BLOOMINGDALE’S | SPLENDID
Sherpa Collar Jacket

4. Joggers That Aren’t Just for the Couch 

It’s a crisp fall morning, and you’re headed out to grab your pumpkin spice latte or go for a morning stroll, and you want to be comfy and cute. Pair your favorite jogger with a fitted tee, chunky sweater, or oversized hoodie, and you’ll be ready to hit the street wrapped in fall comfort

If you still think that joggers are loungewear and just for the chill days at home, it’s high time for a style refresh. 

These comfortwear have officially leveled up, they’re not just lazy-day wear anymore. Joggers are officially in the cozy fall outfit lineup as legit wear, and honestly? They are killing it.

Pair Your Plaid Flannel are Cozy Fall Outfits

laurence-la-medeleine on Unsplas

5. Plaid Flannel with Denim

The warm, deep colors typically found in plaid patterns—like deep red, orange, and rust reflect the changing hues of autumn and the overall fall vibe. Both denim and plaid styles are synonymous with this comfort and style.  

Denim is timeless, right? It pairs well with just about everything. When you combine denim with a plaid flannel, you serve up that chill and chic look that’s hard to beat. This pair is a must-have staple for your cozy fall wardrobe. It’s the perfect outfit for every fall activity, whether it’s a pumpkin patch visit, an apple-picking adventure, or a cozy bonfire night. 

BLOOMINGDALE’S | SPLENDID
Macie Plaid Shirt

ANINE BING
Gavin Jean

Chunky Cardigans Over Everything

Hannah Gullixson on Unsplash

6. Chunky Cardigans Over Everything 

In fall, when layering is key, you can totally throw on a chunky cardigan as a go-to snuggler.  

You can’t have a cozy fall outfit without cardigans. It’s like they’ve secured their permanent spot in the fashion hall of fame, making them a staple in everyone’s autumn wardrobe by their trendy comeback every season and never going out of style.

7. Fleece Jackets for That Extra Warmth 

When it’s cold outside but you don’t want to feel like wearing a boulder, a fleece jacket can give you that lightweight warmth. They are soft, snuggly, and perfect for those chilly autumn days when you want to feel cozy without overheating. And you can always have that extra layer handy without feeling like the Michelin Man.

BLOOMINGDALE’S | CANADA GOOSE
Simcoe Fleece Jacket

BLOOMINGDALE’S | UGG
Sherpa Trucker Jacket

8. Matching Loungewear Sets

Fall is the time of slowing down and embracing self-care rituals and introspection. Having a cozy set of loungewear brings much-needed comfort to enhance your self-care rituals experience. The familiar feel of this loungewear makes you appreciate every moment spent at home, adding warmth to your daily routine. 

Leather Jacket for That Edgy Look 

Pedro Sousa from Unsplash 

9. Leather Jacket for That Edgy Look 

Want to add a little edgy look along with comfort to your fall wardrobe? A leather jacket is the perfect addition. It’s a versatile piece that works for both day and night, whether you throw it over a hoodie, a dress, or a simple tee, it gives your fashion sense and coziness an instant upgrade. 

Basically, if you want to own the season with a look that’s equal parts tough and stylish, a leather jacket is the way to go. 

There you have it! I know dressing up in season and keeping it classy is important, but it doesn’t have to be a struggle. With the right fall fits that feel as good as they look, you can show off your flair and stay cozy at once, just don’t forget to embrace the warm fall feel