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.
-
Looking Stylish This Fall Means Wearing Your Pretty Dresses With This Unexpected ItemHere's how to master the look.
-
Yes, Affordable Cashmere Lounge Sets Do Exist—These Are the 17 Best OnesThese will sell out fast.
-
Anyone Can Wear a Cardigan, But Only Fashion People Wear Them Like *This*Take note.
-
Here's the Comfy Yet Incredibly Chic Boot Style Fashion People Are Already Wearing on RepeatThese make any outfit look more expensive.
-
This Is the Chic Bag Trend Fashion People Swear By Right NowBring on the compliments!
-
These 25 Chic Sweaters From Mango Will Be the Guaranteed Stars of Your Fall and Winter Highlight ReelShop them before they sell out.
-
The 35 Most-Wanted Luxury Buys of Fall 2025, PeriodThe It heels, celebrity-approved handbags, and statement outerwear pieces that are defining the season.
-
These 29 Free People Finds Will Sell Out by November 15Everything we're eyeing (and buying).
