I've Been Keeping Track of My Most-Worn Items—Here's What I Can't Do Without

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(Image credit: @nataliecantell)

My foolproof winter outfit really is my happy place. It consists of seven items (including accessories and outerwear), each of which increasingly exist in multiple versions in my wardrobe. I have dressier versions and more casual versions, and they all mix and match flawlessly.

I've worn some version of my winter uniform probably four days out of seven for the past two winters. It's effortlessly elevated (nothing fussy to fuss with), perfect for schlepping around the city, and always comfortable—which is basically the holy trinity of outfit qualities. Here are my hero winter fashion items in no particular order—including links to some of the exact pieces I own—and others I currently have my eye on.

Oversize Wool Coats

When it comes to wool coats, I'm equally committed to double-breasted, robe, and trench-coat styles. The main thing is the oversize fit and a length that extends well below the knees.

Elevated Belts

Don't underestimate how much wear you'll get out of a really good belt—I have Khaite's Bambi style, and there's no counting how many mediocre outfits it's magically pull together. There's a lot of good options around at the moment that feel rich and interesting without doing too much.

Wide-Leg Trousers

I have such a variety of wide-leg styles at this point, from tailored pairs to elevated knit joggers. I just got the below Ripley style by The Frankie Shop in both deep brown and navy. I have zero regrets. 

Nondescript Sneakers

I like low-tops and gum soles for a bit of a retro vibe in a neutral color way so you can run around all day and get away with wearing them straight to dinner. If it's not that kind of restaurant, then all this outfit needs is a chic pair of flats or heels and you're more than good to go.

Chic Knits

I'm really not sure you can over-invest in knitwear. I like to have some more oversize (menswear sections are great for slouchy cashmere) and others slightly cropped to sit just where they graze the waistband of my trousers.

Statement Scarves

My favorite thing this winter is my Loewe scarf. I bought it in the height of summer when it was restocked and have been waiting for the temperature to dip low enough to wear it ever since. 

Structured Crossbody Bags

The polish of a structured bag is what I think pulls everything together and makes it feel luxe (and keeps my scarf sitting just so). I personally have a thing for great gold hardware on a bag, but that's just me.

Natalie Cantell
Executive Director, Brand Studio

Natalie leads the style direction for the all content we create in partnership with our friends at various brands plus the legendary team of editors who work on those shoots and stories. She loves collaborating and storytelling, so it's a really fun role for her. It's also the first full-time job she's ever had⁠! She started out in her career as a very mediocre model who agreed to her first styling job to impress a photographer she had a crush on, which led her down a happy path of contributing to Vogue Australia and working as a stylist, fashion writer, and creative director for all sorts of brands and titles. She has a bachelor of communications, but most of her career opportunities came up thanks to some fleeting and accidental street style moments. She's been at Who What Wear for three and a half years and still loves to work as a freelance consultant with brands and designers to shoot their campaigns in NYC. She's originally from New Zealand, and Bondi Beach is her second home, but like just about every other 20-something, she fell in love with New York at some point. She lives in Williamsburg with her fiancé and their weird little dog, Ruby. If you ever need reccies for feel-good fashion, legit coffee spots, politics podcasts, or non-intimidating yoga studios, she's very much your girl.