How To Wear Boots With Dresses, Even When It's Truly Frigid Outside


We know all too well that winter can elicit an unfortunately grouchy approach to dressing. Rifling through your drawers in the dark is a chore, and a simple pairing of jeans and a parka feels like your only outfit option. Investing in a statement coat is certainly a step in the right sartorial direction, but even after purchasing, once you're faced with a flurry, a more practical outwear choice pretty much always wins. So, with that in mind, let's move on to another option for infusing a little playfulness into your closet. Opting to ditch jeans or leggings and style your go-to winter boots with a dress instead is an easy way to change things up without risking frostbite. While putting on anything silky or sheer may seem null and void right about now, don't give up hope. In fact, any dress is wearable in the dead of December, it just requires the right inspiration for pulling together a practical-yet-chic combination.

In the spirit of not falling prey to a monotonous winter wardrobe, below are seven ways fashion's top trendsetters accessorize a dress with boots when things get chilly. Based on their ensembles, you'll quickly see that the best approach is to choose a shoe that meets at (or extends beyond) the dress' hemline. This will not only keeps your legs toasty, but it will also create an elongating effect that gets lost when an outfit is broken up by a pair of tights.

Continue onward to discover and digest these seven outfits, and if you find any particularly inspiring (here's to hoping) there is a conveniently similar dress and boots pairing to shop for each.


Yasmin Sewell's ever-so-cool check-printed dress is taken up a notch thanks to a pair of strategically accessorized sock booties that skim the hemline of her frock. (The below is technically a blouse and skirt but they're a matching set, so it totally counts.)

Gingham High-Neck Blouse




Leather Heeled Ankle Boots




Strive for an artistic, painterly duo by teaming a black-and-white printed dress with shade-coordinated boots in a contrasting pattern.

Zebra Print Mesh Midi Dress



Jolene Boots


Anine Bing


Pluck your favorite printed silk dress out of your closet and team it with a pair of thigh-high boots (and perhaps some heat tech). Voila.

Plus Size Long Sleeve Waterfall Hem Dress


Who What Wear

Babs Boots




Balance a ruffled, ankle-length dress with a pair of of-the-moment cowboy-inspired leather boots à la Aimee Song.

Cerise Dress


Ulla Johnson

The Jamie Boots




Test drive a coat-dress for a more structured ensemble. Finish things off with — you guessed it — a splashy pair of calf-high boots.

Finn Cotton-Twill Trench Dress



Jupiter Boots



Maryam Nassir Zadeh


Leaf Greener offers up all the holiday party dressing inspiration you need with this metallic number. Offset the glamour with an unexpected pair of croc-effect or scrunched leather boots in place of strappy sandals.

Assembly Dress


Paco Rabanne

Marfa Knee High 90 Suede boots


Tamara Mellon


Keep this look in your back pocket all holiday dressing season long. The formula is simple: an oversize blazer and a long-sleeve midi dress, plus boots of your choosing. Polish everything off with a statement earring and playful bag.

Finger Hole Jersey Dress




Spirit Boots


Dear Frances