I've Been a Stylist for 14 Years—These 5 Winter Staples Have Never Once Failed Me

It’s funny how some years, it feels almost impossible to shop for the go-to fashion items you love to wear on repeat—for example, if you aren’t a fan of red, I can only imagine the fun you had in 2023 trying to buy a cute sweater in literally any other color. And if you aren’t particularly into barrel-leg jeans, I’m so sorry for the journey you've been on lately.

The good news is, it's the winter of 2024 (very soon to be 2025), and if you’re a fellow lover of elevated basics, this is a great time to be alive and have internet access. There’s really such a lot on offer this season when it comes to shopping for pieces that are chic and effortless, including the handful of winter wardrobe staples I’ve relied on as a stylist. From reliable knits to outerwear to footwear, these are the items that have helped me make getting dressed easy for at least a decade. So whether you’re looking to treat yourself a little splurge (with zero regrets, given the cost per wear) or are sticking to more affordable buys, here are a bunch of ways to shop the six winter items that I never regret shopping.

A Covetable (and Roomy) Bag

Winter means hats, gloves, and scarves, and it specifically means taking them off just about every time you enter a shop or sit down at a cafe. Do yourself a favor, and carry a chic bag that actually has room to stash them.

Slightly Dramatic Coats

A long coat has the power to take even my laziest winter look and turn it into something. Whether your vibe is faux fur, an attached scarf, or just a super-elegant silhouette, a little bit of drama is an immediate outfit upgrade, and my personal shortcut to getting out the door without overthinking my outfit.

Mock-Croc Accessories

Fall and winter outfits sometimes demand mock croc accessories. It just makes sense, I don't make the rules, and I won't be taking any further questions at this time.

Neutral-ish Crewneck Knits

I can't get enough crewneck knits, from my ultra-soft cashmere to some under-$50 styles from Zara that somehow don't mind going in the washing machine non-stop all winter long. Wearing as a sweater if just the beginning—if 2024 has taught us anything, it's that we should also be styling our sweaters as a scarf, and tied under our chins when we're in need of a make-shift hood.

Not-Quite-Flat Boots

There's maybe no greater achievement than finding a great black ankle boot with a heel so tiny it wears like a flat. I find having just that little bit of lift makes such a difference when you need an outfit to work from running around all day to dinner at night—plus a few extra mils can be the difference between jeans that soak up rain off the street, and jeans that don't.