25 Pretty Yet Practical Fashion Items I Plan to Live In This Winter

Most Wanted is a weekly series in which one Who What Wear team member or friend of the brand will share the top 25 finds on their current wish list.
When it comes to my shopping habits there’s no doubt I’ve been leaning towards more practical purchases this season—more time spent at home and in the great outdoors with fewer opportunities to "dress up” for holiday soirée's this year means I’ve been favoring items that are wearable, functional, and comfortable, yet don’t sacrifice on style. In fact, my winter shopping cart is currently brimming with pieces that strike the perfect balance of pretty and practical that are guaranteed to help me feel good, look good, and lift my mood this season.
From striking knitwear to cozy shearling coats and trending chunky boots, there are plenty of Insta-worthy items to luxuriate in this cold-weather season. So sit back, take a sip of hot toddy, and scroll below to see the pretty yet practical fashion items you’ll want to live in this winter.
Up next, 8 easy and economical ways to upgrade your at-home look before 2020 is over.

Judith Jones is the associate shopping director at Who What Wear and has worked in fashion for over a decade. She specializes in shopping content and trend stories with high-affiliate impact. She shares the coolest, most desirable fashion market finds and brands for every budget. Previous to working in fashion, Judith worked as a TV host on the PBS travel show Globe Trekker (airing on Netflix and Amazon Prime) sharing her passion for travel and culture.
-
This Nordstrom Rack Sale Has So Many Cool-Girl Essentials—These 25 Finds Are the Standouts
An extra 20% off? Yes, please.
-
The Classic Hero Piece That Fashion People Reach For All Summer Long
Something for every personal style.
-
I've Lived in NYC, L.A., and Boston—Here's Everything I Think Is Chic for Summer
Shop the highly curated list.
-
The Perfect $16 Tank Top and More Zara Items I'm Texting Everyone I Know About
Elite finds.
-
The 30 Items That Will Define Style in Summer 2025
Gotta catch 'em all.
-
Linen Pants! Full Skirts! Long Shorts! Zara Has Every Single Chic Bottoms Trend—40 Picks That Are Worth Your Attention
Good luck picking just one.
-
3 Aesthetic Pairings to Try If Your Wardrobe's Starting to Feel Stale
Foolproof solutions.
-
27 Crochet Pieces From Zara, H&M, J.Crew, and More That Scream Cool Girl
You'll wear these on heavy rotation.