12 Go-To Indie Winter Pieces That Are Cute & Practical

What's trendy and cute isn't always what's warm and practical for winter — this is a rule we know all too well. And far too often, we end up choosing the former over the latter. But even though it takes just a little bit more effort in the hunt, it is possible to check both the technical and on-trend boxes. So, we're tapping Tictail to help us find the best pieces since unfortunately, the season is far from over.

A native of the East Coast, Tictail's Rachel Fletcher is no stranger to the harsh cold or NYC’s always unpredictable winter weather. When Rachel started working at Tictail, however, her aptitude for surviving (and stylishly thriving!) in the cold increased tenfold. As Senior Retention Marketing Manager, she makes frequent trips to the company’s office in Stockholm, a city known for its dark and seemingly extra-long winters.

Now, several years since her very first trip to Sweden, with many winters under her belt, Rachel’s expertly stocked cold-weather wardrobe has earned her the recognition among her coworkers as the queen of all things cozy — so who better to turn to for a few pointers on the best winter buys this season? Because let’s face it, we still have two more months of winter ahead of us. Might as well weather the cold looking cute.

"Layers on layers on layers. Siizu makes the best sweaters that are the ultimate in practical winter dressing."
SiiZU THE CREW NECK MERINO SWEATER, $95.00 Buy
"High-waisted, super cozy flannel pants make warm-but-cool dressing a breeze."
IFEELNUT Pantalon Diom, $60.00 Buy
"This vegan handbag looks warm enough to wear, and it can fit all your extra winter layers with ease."
Saint Catello FAUX FUR BODEGA BAG, $165.00 Buy
"Some people say they can never have enough shoes. That’s me and navy (or grey, or black) turtleneck sweaters. 'Staple' is an understatement."
Chicatory Mohair blend oversized turtleneck pullover for women, $61.00 Buy
"Big beanies are the best beanies, especially when made with love (and the perfect pop of color) in Paris."
Trust the Mojo GO BIG OR GO HOME BEANIE - Honey, $87.00 Buy
"It’s soft, it’s chic, and it’s got most functional feature of them all: pockets!"
ESP POCKET SCARF DARK CAMEL, $65.00 Buy
"These very grown-up mittens are made in Finland (so you know they’re warm), with ethically sourced shearling."
ONAR Studios DALUM Gloves Almond, $313.00 $38.00, Buy
"This is a sweater for your entire body. It’s perfect for a winter workday paired with a boot and a button-down."
Rita Row Rita Row - Harper Jumpsuit Mint, $163.00 $98.00, Buy
"Still here for the full body sweater look, and the 90s throwback zipper is functional and fun to look at."
Juanma KNIT BLUE DRESS, $263.00 $225.00, Buy
"I’m all about cute + functional—but I definitely skew toward functional. If a garment can cover my head, my neck, and my knees and still look cool, it’s pretty much a guaranteed purchase."
I Dig Denim Noah jacket, Green, $242.00 $121.00, Buy
"These boots are the dream. The platform make them super modern, but they’re rugged enough to brave all the puddles and potholes of winter."
Kupuri COOPER 500 MILITAR, $324.00 $136.00, Buy
"Two reasons to buy these boots: 1. Winter whites are seriously underrated. 2. These boots are 100% leather, handmade in Portugal, and cost less than $100. (Okay that’s, like, five reasons!)"
Ten Points New Carol, $165.00 $64.00, Buy
written by Annie Georgia Greenberg; appearance by Annie Georgia Greenberg; edited by Christopher Michael Beer; shot by Jack Pearce; shot by Kenny Wu.
Related Video
Show More Comments...