The prospect of a socially distant winter isn’t exactly uplifting, so this holiday season, give immediate cheer to anyone on your shopping list who cares about style. In choosing these gifts, our obsessive editors focused on clothes and accessories that your loved ones will want to wear right away. Nothing silly. Or frivolous. Nothing outré that your giftee might finally try on in late May, once he or she has had a couple strong drinks. And we’re not in the mood for outlandish extravagance this year. Everything here rings in at under $300, from a plush shearling hat to one-of-a-kind coats (perfect for socializing outside) to, believe it or not, diamonds. 

A Cozy Trapper Hat Named for Brad Pitt

Wearing a trapper hat is an easy way to “feel like you’re in the mountains or skiing” during a winter with limited travel options, suggests New York designer Nikki Kule. Her eponymous brand’s rugged-chic hat, dubbed “The Pitt,” is made from 100% shearling and named for the equally rugged-chic Brad Pitt (who played no role in its creation or marketing). A perfect gift for skiers, wannabe skiers, ’70s fashion adherents and “Fight Club’” fanatics. $298, kule.com

A Dress That’s Its Own Special Occasion 

These made-to-order dresses from Brooklyn-based label Fanm Mon, available in a range of pastels, are the pick-me-up your recipients need this holiday season, pretty just for the sake of being pretty. While Pierre-Sophia Demirtas, the label’s founder, appreciates the merits of jeans and T-shirts, she said, “Some days you just need to put on a beautiful dress that’s going to give you that same comfort and functionality.” She wears hers to repot tomato plants (not included). Salda Dress, $199, fanmmon.com

A Colorful Coat You Design Yourself

Kids hate wearing jackets. Toddlers resist having their arms forced into puffy sleeves. Tweens “forget” their coats on the bus. This season, make the hateful joyful with a customizable Ralph Lauren jacket that lets children create their own patchworked puffer, specifying colors for the sleeves, body, hood and zippers. Your kid will want to craft his or her Mondrian-esque masterpiece online right away with the promise of a package to come—the coats ship in three weeks. Kids’ Custom Packable Hooded Jacket, $185, ralphlauren.com

Socks as Comfy as Sweatpants

2020 has been the year of the sweatsuit, so why not take the trend to its logical conclusion by giving sweats for the feet? Before you roll your eyes: These particular socks-—notably comfier and thicker than most—practically compel laziness. We’re not just blathering on about thickness, either. Each sock features two layers: a merino-wool blend exterior and an interior of cotton pile, which mimics sweatpants’ addictive softness. RoToTo Socks, $29, standardandstrange.com

This post first appeared on wsj.com

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