Shoes

Five Cute Ways to Pair Dresses and Boots This Winter

Pair Dresses and Boots

Winter is upon us, which means it is time to switch up your wardrobe accordingly. Whether you embrace the cold or long for warmer days, getting your closet ready for chilly temperatures will help you make the most of this season’s fashion potential. 

Fashionistas everywhere love pairing dresses with boots to get a stylish head-to-toe look that is ready to go anywhere. Why are dresses and boots a great winter outfit option? This look can easily be dressed up or dressed down, making it the perfect choice for everything from a New Year’s cocktail party to a coffee date with friends. No matter how you choose to express your personal style, there’s a way to rock dresses and boots this season. Here are some of the most chic ways to wear this style pairing. 

1. Chelsea Boots and an LBD

When two classics come together you absolutely can’t go wrong, which is the case when you don a pair of Chelsea ankle boots with your favorite LBD, or little black dress. Chelsea boots are ankle-length boots—usually leather or a leather lookalike—that have been around since the 1900s and was originally popular among both equestrians and big city dwellers. The style is also practical: Most Chelsea boots have elastic inserts on either side, making them easy to slip on and slip off if you’re in and out a lot. 

Rocking a pair of Chelsea boots with an LBD conveys a classic sense of style that will be right for any occasion, from holiday cocktail parties to job interviews. Accessorize your outfit with a well-chosen pair of earrings for some shine or add a favorite scarf for a more casual finishing touch. 

2. Combat Boots With Florals

You don’t have to be a punk rocker to don combat boots anymore. Fashionistas everywhere are rocking chunkier style boots, like Dr. Martens, with daintier dresses for a fun ensemble that offers lots of visual interest. The key is contrast: the edgier shoes look fun and fresh when paired with an unexpected pattern like a floral or a delicate print. 

Another way to approach this look is by donning shooties with edgier elements, like studs or laces, if going full on combat boot still feels a little intimidating to you. Just keep your tights simple here so you don’t feel too overloaded—opaque black tights will be just right.

3. Knee High Boots With a Short Dress

This look at all about attitude! Just because it is winter doesn’t mean all of your short, flirty dresses need to be put away until the warmer weather returns. For a sultry date night or going out look, you can’t beat the combo of tall boots and a short dress for some serious va-va voom

Knee high boots channel sophistication and elegance, whether you choose to go with flat boots or sky-high stilettos. And knee high boots are available in lots of materials, like leather, velvet, and suede, to add texture to any outfit. Plus, knee high boots are practical in the winter and will help keep your feet and calves snug. Winter designer dresses for ladies are perfect for pairing with boots for a stylish and warm winter look. Pick your favorite mini skirt, skater dress, or cocktail dress and get ready for an incredible look that only needs some understated jewelry and a swipe of lipstick. 

4. Patterned Boots With a Maxi

Go big or go home! This look combines the drama of a maxi dress with the cool-girl chic of a pair of statement shoes. To achieve this swoon-worthy style, go simple with your dress: a classic cut in an understated material in a solid color. This will give you a good canvas for letting your shoes shine and make sure your overall ensemble feels balanced. 

Once you’ve got your dress locked in, now it’s time for the fun part! Seek out boots with a cool pattern, like a floral boot, snakeskin boot, or animal print to add lots of personality. High-waisted cheeky bikinis can be paired with matching pair dresses and boots for a stylish and coordinated look. The vividness of your shoe means that you can keep most accessories toned down—opt for a simple crossbody purse, a cuff bracelet, or pair of earrings to add some shimmer without going too over the top.  

5. Shearling Boots and a Sweater Dress

Cute winter style is all about texture, and in this case, your winter dress choices will also help keep you warm and cozy. Sweater dresses are a winter weather fav and come in a variety of styles, from fair isle sweater dresses that evoke time-cherished patterns to more sleek varieties that wouldn’t be out of place at your favorite swanky happy hour. 

Pair dresses with boots for a perfect outfit for your workouts that is both stylish and functional.

Pair a sweater dress with some women’s boutique shoes for an ensemble that is equal parts comfortable and chic. The shearling details on the boots will complement the softness of the sweater, creating one perfect outfit for wine bar dates with someone special or a cozy movie night at home. This is also a good look for when you need to do a lot of walking and want to feel comfortable on your feet!

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