e’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.
PHOTO: @SAMANTHAAELISE
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.Shop the look:
COS Organic Cotton Oversized Trench Coat ($250)
H&M Single-Breasted Jacket ($50)
New Balance 990 V5 Sneakers ($185)
A knit set is fail-safe.
PHOTO: @VENETI.A
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.Shop the look:
Who What Wear Collection Coco Cropped Turtleneck Sweater ($95)
Who What Wear Collection Felix Midi Skirt ($95)
Miista Block Heel Penny Loafer ($410)
ACNE Studios Musubi Leather Maxi Bag ($1550)
Add tights to your summery dresses.
PHOTO: @MARIAALIA
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.Shop the look:
Re/Done 90s Oversized Crewneck ($475)
Open Edit Satin Wrap Skirt ($59)
Commando Ultimate Opaque Matte Tights ($36)
Who What Wear Sowyer Platform Chelsea Boot ($149)
Pull a Mary-Kate and Ashley Olsen.
PHOTO: @NIKI_INTHECITY
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. Shop the look:
Herou Long Sleeve Turtleneck ($17)
Who What Wear Collection Norah High-Waisted Trousers ($155)
Koio Bari Loafers in Glossed Black ($298)
The Row Large Slouchy Banana Leather Shoulder Bag ($2250)
Dollger Rectangle Sunglasses ($12)
Yep, it’s time to break out your puffer.
PHOTO: @KRISTENGRACELAM
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.Shop the look:
BP Oversized Puffer Jacket ( $79) $63
Levi’s Ribcage Straight Ankle Jeans ($98)
Converse All Star ’70s High Top Sneakers ($85)
Burberry Alchester Convertible Satchel Horseferry Check Canvas Small ($865)
Lack of Color Wave Bucket Hat ($89)
Stick to a single color family.
PHOTO: @ANIYAHMORINIA
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.Shop the look:
Mango Quilted Cross Jacket ($120)
Mango Wide Leg Pants with Pockets ($50)
Aeyde Carly Pointy Toe Ankle Bootie ($445)
Velvet Canyon Revolution ($289)
Swap the jeans for a pair of leather trousers.
PHOTO: @NOORE
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.Shop the look:
Understated Leather Howling Moon Suede Bomber Jacket ($398)
Bdg Urban Outfitters Ringer Baby T-Shirt ( $34) $20
Who What Wear Collection Eli Relaxed Vegan-Leather Trousers ($155)
Open Edit Lucia Platform Bootie ($70)
Let your sweater do all the talking.
PHOTO: @SQUAREPEARLS
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.Shop the look:
Eloquii Pintuck Wide Leg Pant ($80)
Mango Pointed Heel Ankle Boot ( $60) $26
Apede Mod Deco Line Bag ( $395) $237
Lean on quirky accessories.
PHOTO: @LUCYRAEMCFADIN
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.Shop the look:
The Open Product Zip Up Balaclava ($73)
Sandy Liang Green Happy Cardigan ( $475) $271
Afrm Dawson Ribbed High Waist Wide Leg Pants ($68)
Adidas Samba Classic Sneakers ($60)
Don’t take shorts off the table (yet).
PHOTO: @GRACECAROLINELARCADE
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.Shop the look:
Who What Wear Collection Tanya Tie-Waist Jacket ($200)
BlankNYC Faux Leather Paperbag Waist Shorts ( $98) $50
Nordstrom Opaque Control Top Tights ($15)
Bottega Veneta Color Sole Chelsea Boot ($1280)
Go matchy matchy.
PHOTO: @DANIE.SIERRA
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.Shop the look:
Free People FP Movement Rocky Ridge Pullover ($148)
ACNE Studios Bertine Booties ($590)
Speaking of winter, these six loungewear trends are promising to be huge.
