16 Dr. Martens Outfits Our Readers Are Loving This Winter

Welcome to #WhoWhatWearing, a series in which we highlight you, our stylish community of readers. Each of the following looks came straight from a photo you tagged us in on Instagram. Want to be featured next time? You guessed it: Use #WhoWhatWearing on the outfit posts you want us to see.

If there's one boot style whose popularity never fades, it's Dr. Martens. What was once reserved for the grunge and punk rock crowd is now in the closet of virtually every fashion person we know. While their audience has varied over the years, these iconic boots have been a wardrobe staple for decades, and we don't see that changing anytime soon. The thick soles make them the ultimate winter boots—and the under-$200 price tag is an even bigger selling point.

Whether you're just jumping on the Dr. Martens train or have been a loyal fan for years, an array of fresh outfit ideas never hurt anybody. This is where I turn to our stylish readers for guidance—and they're wearing these chunky boots with everything from puffer coats to maxi dresses. Keep scrolling for 16 Dr. Martens outfits that can only be described as genius, and then shop the famous boots for yourself.

I never knew I needed white Docs—until I saw this outfit.

All-black everything is always a good idea.

These look beyond cool with plaid.

Also pairs well with dresses. 

Raise your hand if you need white Docs now, too. 

Patent leather + Dr. Martens = ultimate winter pairing.

Yes to everything happening here (including the dog). 

Meet your next travel look.

Spice up your all-black outfit with colorful outerwear.

Dr. Martens were basically made for skinny jeans.

They also play well with straight-leg styles.

Bet you never thought to wear your Docs with a sweatsuit.

A weekend look if I've ever seen one. 

Neon and Dr. Martens feels very '80s—in the best way.

Velvet Dr. Martens just shot to the top of my wish list.

I'll be wearing this on my next flight, no question.


Ready to show us your looks? Tag @WhoWhatWear on Instagram and use #WhoWhatWearing for a chance to see them end up here! Next up: how our readers are wearing this winter's biggest outerwear trends.

Related Stories