32 Chic Under-$100 Winter Items That'll Make You the Object of Envy

As winter approaches, I’m all about finding stylish, budget-friendly pieces that keep me looking chic without spending half of my paycheck on an item or two. Luckily, retailers like H&M, Zara, and Mango are offering a wealth of options that marry both affordability and fashion-forward design. Whether I’m hunting for a timeless wool coat, a cozy cashmere sweater, or a pair of sleek boots, these stores deliver the kind of winter essentials that elevate my wardrobe while keeping my bank account intact.
As a fashion editor, I'll let you in on the little secret that keeps my outfits looking triple the price: It’s all about knowing where to shop and finding pieces that feel luxurious without the price tag to match. Below, shop some of my favorite under-$100 winter pieces that everyone will be admiring from afar.
If you love the vintage earring look without the size, this mini version of Heaven Mayhem's knot earrings are right up your alley.
In lieu of black leather pants, this deep, rich mocha hue makes them feel a bit more elevated.
Channel the elegant Upper East Side ladies who lunch with this timeless cashmere wrap.
This jacket looks triple the price (and nearly identical to the designer version on my Pinterest board at a fraction of the cost).
Barn jackets are our collective obsession for fall and winter.
Hear me out: Pillbox-style hats and caps are going to come back in a big way this winter.
Barrel-leg jeans have been having a moment all of 2024, and I suspect this trend won't be on the chopping block from January 1.
Don't walk—run. This chic coat is on sale for Black Friday.
Prepare to be the most well-dressed employee at your company's holiday party with this two-toned mini.
I have a soft spot in my heart for ultra-dark-wash denim.
Ana Escalante is an award-winning journalist and Gen Z editor known for her sharp takes on fashion and culture. She’s covered everything from Copenhagen Fashion Week to Roe v. Wade protests as the Editorial Assistant at Glamour after earning her journalism degree at the University of Florida in 2021. At Who What Wear, Ana mixes wit with unapologetic commentary in long-form fashion and beauty content, creating pieces that resonate with a digital-first generation. If it’s smart, snarky, and unexpected, chances are her name’s on it.
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