How To Wear a Shift Dress Now Through Winter


Gang, for this week’s Just Delivered, I wanted to focus on a piece that I think is really special:  Free People’s suede shift dress.  It’s available in a ton of colors, reviews are off the charts, and it’s the kind of piece that endures.  Modern, but timeless.

Furthermore, the tips I’ve come up with to style this piece from warm weather, through Fall, to winter weather can basically be applied to any little shift dress.  (I’m wearing an xs for reference).  Links to everything else below.

Hope you enjoy!

Warm Weather Styling

With Sneaks
Adidas Sneakers

Over Jeans:
AG Jodi Crop Flares
FRAME Le High Flare Jeans
Dolce Vita Mazey Block Heel Boot

WIth a Tshirt:
James Perse Sheer Slub Crew Neck Tee
Free People Cecile Ankle Boot – these are my fav sock boos, but you can see a ton of other options in our Fall Boot Guide

Fall Styling

Cute Toppers:
J.Crew Cardi Blazer (size xxs for reference)
Madewell Oversized Jean Jacket (xxs for reference)

With a Flannel:
Paige Denim Flannel Shirt (xs for reference)

Winter Styling

With a leather jacket and layers:
Stuart Weitzman Lowland Boots – but you can see more Over-the-Knee boot favorites in our Fall Boot Guide

IRO Leather Jacket – wearing a 38 to better fit over sweaters.  This jacket is pricey, but if you are looking for a good mid-range one, this All Saints leather jacket or Madewell’s washed leather jackets are our team favs. (Article coming soon!!)

Red Waffle Knit Scarf


  1. I prefer the old format with less video content. It’s much harder to check in on the go or in public spaces. Love the site and content!

  2. There have been several recent “multiple ways to wear x item” posts. This is what your long-term, loyal readers want (at least this loyal 43 year old working mom)! Thanks for putting this together!

  3. Love this video. I usually don’t go for the shorter dresses, but I’m gonna see if some of the cute Free People dresses I got this summer (thank you Anniversary Sales) will work over skinny jeans. It’s a crew neck top, but hey, I am totally willing to try some of your ideas. Love this video! Great job

  4. These videos are so great! Question: If you can’t do bare legs, would you wear black tights in the cooler weather with the black sock bootie? And what if the dress was black–still black tights with black or patterned statement booties? Ongoing dilemma of mine. I have a cute floral swing dress that looks awesome with tan booties, but I don’t know how to cover my legs..suggestions?

    • Yes, this! I’m in Maine and work in a law office. No bare legs for me in the late fall/winter months. I loooove dresses and skirts and would love to see some ideas for tights and different show types.

  5. I have a faux suede dress in the same cut I got years ago, so cute AND washable! Thanks for the ideas, I’m gonna go pull it out from the back of my closet now!

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