How To Dress for the Holidays, According to our Head of Design, Joyce


If you’ve ever stared into your closet at this time of year and thought, “I have nothing to wear,” this is for you.

It’s more than just festive gatherings that add sartorial pressure. It’s the sheer number of holiday events that require very different looks. One person who can relate: our head of design, Joyce. Her secret to staying sane and stylish through it all? A few really great go-to outfits that make her feel exactly like herself. Joyce’s take on holiday dressing, in her own words:

Wearing head-to-toe denim somehow makes running errands a little easier. One allover color feels calmer, and denim is like protection against the elements. (It can really tackle the season with you.) Even a woman loaded down with shopping bags looks great if she’s wearing a denim coat and boots.


I love jumpsuits for any occasion—there is no easier way to get from work to dinner because all the changes happen at my desk. Wear one with a sweater during the day and then switch to a leather jacket, change into heels and add a hat for a night out. (Side note about hats: I wear them year-round. If I’m stuck getting dressed, I throw on a hat and instantly feel finished. In general, I think women look strong when they wear them.)


A plaid shirt isn’t the obvious choice for a night out, but that’s why I love it. I always want an element that makes me feel like myself, and a graphic pattern or even stripes are much more “me” than a fancy dress. Plus, a shirt is easy to tuck into wide pants. Add a thick heel and you’re done. During the holidays especially, feeling good leads to looking good.

Top: Joyce is wearing our Denim ParkaSlim TurtleneckFlea Market Flares, Madewell & Biltmore® Fedora and The Transport Tote.
Center: Joyce is wearing our Washed Leather JacketFaux-Wrap Cami Jumpsuit, Madewell & Biltmore® FedoraThe Morgan Crossbody Bag and The Hanne Heel.
Bottom: Joyce is wearing our Flannel Oversized Boyshirt and Caldwell Trousers.

Shop our newest arrivals here and shop our #Giftwell Guide here.

Photography by James Ryang.