5 Weekend Outfits That Prove It’s Possible for Comfort and Style To Coexist

Let’s get one thing straight: I moved to New York City to become the next Carrie Bradshaw (me, and the 3,876 other girls that came before me). I mean, I have her job (sorta), I love fashion, and I live in an apartment I can’t afford (dreams don’t come cheap around here). But after a recent stroll through Central Park gone wrong and a suede sneaker casualty later, it’s clear that I will never, ever, be her. So while I may pretend to lead a stylish, Carrie-infused life, more often than not, you’ll find me in jeans and a tee, nary a Jimmy Choo in sight. 

But just because I’m not sporting a pair of three-inch stilettos on the weekends doesn’t mean that I’m not still waiting on a call from the producers of SATC. After a couple of years of adjusting to life in NYC and a very tumultuous breakup with my Lululemon leggings, I can confidently say that yes, looking chic while remaining comfortable is possible. (Spoiler alert: It looks like I wasn’t the only one with this realization, since SJP made her return to our screens in the 2021 premiere of And Just Like That in a pair of—brace yourselves—flats.) With just a few easy swaps, you can confidently enter the weekend in comfortable, weekend-ready outfits that don’t feel like they sacrifice style.

Whether you’re meeting a friend for coffee, making your Sunday grocery run, or finally getting around to dropping off those late returns, here are five weekend-approved, casual-cool outfits to wear on repeat this fall.

For popping into your local bookstore

Sweater (Plus) | Tee (Plus) | Jeans (Plus) | Bangles | Socks | Mules | Shoulder Bag

Now, I’m not one to boast, but I fear that I must: I’ve somehow managed to encapsulate all of the feelings associated with the word “cozy” into this outfit. All that’s missing is a good book, a pumpkin-scented candle, and a cup of coffee. Oh, and if you haven’t picked up a pair of cashmere socks yet, this is your sign to—you simply have not experienced true luxury until you’ve experienced cashmere for your feet.

For grabbing a quick morning coffee

Jacket (Plus) | Hoodie (Plus) | Sweatpants (Plus) | Hat | Mules | Bag

Take your cozy sweat set from “I’m not leaving my apartment today” to “I don’t mind if I run into someone I know in this” with the addition of a leather jacket and contrasting pair of shoes. The studded mules and trendy bag make this look feel intentionally styled rather than like you just ran out of the house in your pajamas.

For a day of running errands

Sweater | Tee | Track Pants (Plus) | Flats | Shoulder Bag | Sunglasses

My heart belongs to whoever decided track pants are cool again. They give a similar effect to trousers, but with the same level of comfort as, say, your jeggings from 2009. By pairing them with a crewneck sweater, you have a look that achieves the maximum level of comfort for a day of errands. Bonus points if you follow the wrong-shoe theory and pair this look with flats rather than a more obvious choice like sneakers.

For heading to a Farmer’s Market

Trench Coat (Plus) | Tee (Plus) | Loafers | Necklace | Tote Bag

On paper, a loafers-and-trench-coat duo might sound like an office outfit, but when styled with a long-sleeve tee and elastic-waist pants, the once workwear-dubbed combo makes for an undeniably chic off-duty ensemble. Plus, opting for traditional silhouettes in non-traditional colors—like loafers in a metallic shade of gold— will help to lessen the level of formality.

For a day of shopping

Blazer | Jumpsuit (Plus) | Socks | Sneakers | Earrings | Phone Strap

Although I said I technically broke up with my Lululemon leggings, I’m not above a sweat-wicking jumpsuit. It’s not my leggings’ fault—it’s more of a “it’s-me-not-you” type of thing after deciding that I needed to break free of the black leggings I used to rely on. I love an athleisure onesie because it’s a one-and-done outfit that looks incredibly chic with a juxtaposed layer like an oversized blazer or an open cardigan. Just add a few intentional accessories and you’re good to go.

ABOUT THE AUTHOR

Tinsley Crisp, Fashion & Beauty Staff Writer

Tinsley Crisp is a Fashion & Beauty Staff Writer at The Everygirl and specializes in reporting on the season’s latest trends and hottest products. As a New York City-based stylist, she’s committed to injecting joy into the art of getting dressed and delivering attainable yet aspirational content to our readers.

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