11 Fall-to-Winter Outfits My East Coast Friends Will Actually Wear

fall-to-winter outfits



We've hit that weird time of year. It's definitely sweater season and kind of coat season too. Figuring out what to wear when it's almost freezing (but not quite) can be confusing. But all it takes is some fall-meets-winter outfit inspiration to help you dress appropriately. Instead of resigning to leggings and sneakers, we're here to offer different ideas. Here on the East Coast, the first flurries have fallen and winter is definitely on the brain.

To keep you filled with outfit inspiration for this tricky transitional period, I scanned the Instagram feeds of my stylish fashion friends and am pleased to share the below 11 'fits. Packed with cozy layering tricks, stylish ways to wear coats, and ensembles to keep warm but not sweaty, here's your guide to nailing dressing this time of year. So break out your puffers and turtlenecks, but don't put away your skirts and dresses just yet. Ahead, see the fall-to-winter outfits that NYC-ers are sure to wear, and shop pieces inspired by their handy styling tricks.

Double down on outerwear.

Winter demands that you become a master at layering. One styling trick I always see cool East Coasters following is to throw a trench or wool coat over a blazer, especially one in the same color family. It creates a dimensional effect that looks like you tried a lot harder than you did.

A knit set is fail-safe.



Don't overthink it. A matching knit skirt set with your favorite flats or boots is the easy 'fit you'll be wearing all winter long.

Add tights to your summery dresses.



Don't bury away your lightweight slip dresses just yet. Wearing one as a skirt with a pair of tights underneath and a chunky knit on top transforms the dress into a cold-weather-friendly skirt.

Take after the queens of effortlessly cool style, the Olsen sisters, and top off pretty much any outfit with a long, ankle-grazing coat for a chic finish. 

Yep, it's time to break out your puffer.

If you're anything like us, you know that jeans and sneakers are a year-round type of thing. To transition them from fall into winter, simply swap your lighter layers with a tried-and-true puffer coat.

Stick to a single color family.

Don't underestimate the power of a monochromatic outfit. A palette of head-to-toe cream, beige, and ecru tones looks masterfully styled even if you put in minimal effort.



While winter certainly won't stop us from wearing jeans, leather pants are the wardrobe staple that is taking on new importance in our closets this time of year. Style them as you would any pair of jeans, e.g., with your other staples like a T-shirt and black boots.

Let your sweater do all the talking.



There comes a point in the season when you can't escape the necessity of wearing a coat, so why not push the inevitable until you absolutely have to? Instead, let a bold sweater do all the talking.

Lean on quirky accessories.

Just because you're bundling up more now doesn't mean that creating a cool look is out of the question. Lean into quirky accessories that do both, like an of-the-moment balaclava.

Don't take shorts off the table (yet).

Shorts? In the winter? Groundbreaking. This season, fashion people are all about one unexpected winter item, leather shorts, which they're styling with boots and tights.



With lots of layers to consider, try coordinating them in the same color family for a cohesive ensemble. For instance, match your boots to your jacket, as Danie did here. It's subtle but really pulls the look together.

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