10 Best Ways to​​ Style Dresses With Boots in a Winter

With the temperatures still dropping and the winter period full onboard, boots are the obvious footwear choices. You can hardly go wrong by styling a dress with boots as most of them are effortless to put together, yet look amazing. As we are waiting for the spring season to roll into course, your favorite winter and fall dresses can be put to good use in perfecting your winter wardrobe.

Winter boots with dress are usually in default colors like dark tones or neutrals such as beige and off-white. You can overstep the limits to go full-on fresh with a hot red or neon pink boot selection. The same goes for dresses, you can switch the conventional winter shades for your favorite colors and hues. Below are some easy ways to style dresses with boots and look comfortable all day:

  1. Blazer Dress with Black Knee-high Vegan Leather Boots

The best part about pairing winter boots with dress, especially a blazer dress style, is that there are no limitations to the extent of your creativity. You can wear a double-breasted blazer dress with black boots, a fitted and belted blazer with the same boots, or a boxy oversized blazer dress with some comfy Slouchy boots. Any of the above pairs can level up your wardrobe for a holiday party, some serious boss chic vibes at your workplace, or even an elegant number for a fancy restaurant. Black, white, navy, tan, and plaid blazer dresses are commonly paired with leather knee-high boots, but you can break free from the crowd with a statement-making color like red.

  1. Long Sleeve Bodycon Dress with Pointed Toe Thigh-high Boots

A black dress for women should have a place in your closet because of how versatile it can be. They are functional throughout the year and you can bet on them when you aren’t sure of what to wear for an event. This black-on-black blend can help keep you insulated regardless of how low the temperature drops. A black bandage dress with boots in a pointed-toe leather heeled style brings an edgy aesthetic to your ensemble. The beret and shades seal in the statement and bring your personality to your outfit. You can wear lace tights under the dress to ensure you don’t catch a cold.

  1. Knit Wool Dress and Block Heel Ankle Boots

Whether you’re rocking a mini, midi, or maxi knit dress, a pair of ankle boots can be a stunning addition to your outfit. A warm thick outerwear like a faux lamb leather coat serves as the perfect layer to handle the cool weather. However, you can wear yours with a simple but chic sweater. If you’re not a sucker for black footwear, opt for earth-tone suede ankle boots with block heels. Also, do you know what would be a great alternative to the block heels here? Patent leather clear ankle-heeled boots with zipper details.

  1. Shirt Dress with Lace Up Combat Boots

Ruched dresses have a way of making you stand out from an audience, and to look amazing effortlessly, fewer ruching may be your best bet. Cute ruched dresses in the shirt style can amp up your glam when paired with fancy combat boots. Be it leather patrol boots, German army para boots, or cadet boots, as long as they are combat, they will look amazing with a shirt dress. This combo is a plus for the winter period as you can wear them as a transitional outfit in fall or during the early winter weeks. Not in the mood for some military footwear vibe, style dresses with boots like lace-up, ugg, or Wellington boots.

  1. Turtleneck Sweater Dress with Snakeskin Print Boots

A snuggly yet chic outfit you can wear this winter season is an oversized sweater dress and tall snakeskin boots.

If you’re looking to have some fun with your fashion staples, opt for snakeskin or leopard ankle boots with rugged lug soles. A scarf and beanies are a tempting fashion style and you’re sure to get addicted to all the warmth from the different pieces. A cute shoulder bag is just about the necessary purse you need for a few essentials.

  1. Skater Dress with It Girl Platform Laceup Boots

Skater dresses and tennis skirts can look really good with the right pair of boots. And since it’s winter, the right sweater or cardigan would go beyond serving as a styling piece to becoming a necessity in your outfit. A cozy sweater over your dress can help provide added warmth for the winter season. You can double up on the cozy notes by wearing thick knit socks under your boots. A skater dress with boots in the platform lace-up style is something you can pull off if you’re aiming for a casual ‘It-girl’ style.

  1. Midi Knit Dress with Satin Stretch Stiletto Heeled Ankle Boots

You may be rocking a lot of boots this winter. An easy way to add some style to your selection will be to wear your stiletto ankle boots with a midi knit dress. You can rock the combo to a casual work setting, a party, or to hang out with friends. While knee-high boots are arguably the best picks for midi dresses, satin stretch ankle boots can also work for the outfit. A matching bag and belt combo with your boots can perfect the elegance of your blue wool dress backdrop.

  1. Ribbed Knit Dress with Stiletto Slouchy Boots

Knee-high boots, combats, and ankle boots are easily the go-to boots for knit dresses. Since you’re aiming to look your best, Slouchy winter boots with dress can break the ice and set an air of difference at any event you attend. The long-sleeve style makes for a cozy winter apparel, and the thigh slit helps to keep style in check. And to ensure that function is not overlooked, the slouchy boots double as pants and warm up the legs. The boots step up the glam of the outfit hence you’d need to accessorize correctly to maintain that level of elegance.

  1. Colorful Backless Halter Dress and Patent Leather Neon Pink Booties

Who says you can’t bring your slick Barbie spirit to winter? A colorful backless halter mini dress embraces Barbie’s playful side and you can seal in the look with complementary patent leather booties. To pull off this look in winter, consider pairing it with a comfy trench coat—to avoid freezing up when you step outside. This would look great if your coat is also in a soft color or one of the dress colors.

  1. Midi Thigh Slit Dress with Raven Chunky Block High Heel

This midi dress and chunky boots may look complex at first but are super simple to pull off. To style dresses with boots in this way, your color combinations have to be on point. You can show a little skin through your slit if you don’t mind or put on some tights for extra coverage. However, the plaid coat already serves the part, so you can skip the tights. Since the dress is a bit long, ankle boots are pretty much the best length, and you can take the style up a bit with a chunky selection.


There are many ways to wear boots with dresses and look instantly stunning. Any boot style be it ankle, knee-high, thigh-high, combat, Chelsea, sock, or Western booties, can look super chic with a dress and still keep you warm.

During the last winter months, you may need some extra layers to keep you cozy, however, these dress and boot combos will have you looking stylish (and with the least effort) without compromising comfort.