How To Wear Boots With a Dress

From knee-high boots to combat boots, cozy sweater dresses to breezy sundresses, boots and dresses are two versatile pieces that can elevate your style year-round. 

With so many styles, lengths and colors to consider, you may be feeling overwhelmed with options. Never fear — we're here to help narrow down your choices!

Learn how to wear boots with dresses with this complete seasonal styling guide. No matter the time of year or your desired look, we'll help you create stunning outfits to set your wardrobe over the top. Read on to gather your outfit inspiration.

Fall and Winter Dresses

When you're adding the trendiest fall and winter outfits to your wardrobe, it's essential to also choose clothing that keeps you comfortable in dipping temperatures. Thankfully, you can have the best of both worlds with the stylish and comfortable outfits we've listed below.

It's best to layer light, breathable fabrics in the early fall and move into thicker options as the weather cools. When selecting winter dresses with tights and boots, try to opt for heavier fabrics such as fleece, wool and cashmere. These cozy materials are ideal for keeping warm in cooler temperatures while ensuring you stay in fashion. 

Keep reading for some excellent dress and boot pairings for crisp, cool weather.

1. Sweater Dress and Knee-Highs

Need an outfit that keeps you snug and stylish during the chilly seasons? Consider a cozy sweater dress with some trendy knee-high boots. 

If you prefer an understated look, keep your outfit to one or two colors. Try pairing a white or gray sweater dress with a pair of black boots for a classy and elegant look, or rock some earth tones with a taupe sweater dress paired with knee-high boots in a rich brown.

If you'd like to add some more color to your look, we recommend sticking to an autumnal palette. You can pair a mustard yellow, rose, army green or burgundy sweater dress with some neutral-colored knee-highs. While black boots complement nearly any outfit, you can opt for a tan, nude or brown pair as well. Mix and match colors to see which ones complement each other best.

If it's particularly cold outside, add some tights to the mix. When deciding how to wear tights with dresses and boots, we recommend selecting a neutral color such as black, gray, tan or nude. Brightly colored tights can divert focus from the rest of your outfit.

2. Wrap Dress and Heeled Boots

Create a trendy boho look by pairing a wrap dress with your choice of heeled boots — we recommend knee-high or ankle boots. Wrap dresses come in a variety of lengths, styles, colors and patterns, giving you plenty of opportunities to create stylish and comfy outfits for any season.

During fall or winter, we suggest choosing a long-sleeved maxi-style wrap dress to help you stay warm. While you can choose any color or pattern you please, be sure to choose one that complements your boots! Like most types of shoes, neutral-colored boots in black, brown or gray generally pair nicely with most dress colors and patterns.

If you decide on a shorter wrap dress, it's a good idea to add some tights to keep your legs warm. Use the current outdoor temperature and your best judgment when selecting a wrap dress and boots to wear.

3. Bodycon Dress and Ankle Boots

If you're looking to turn heads with your trendy cold-weather outfit, try a bodycon dress with heeled ankle boots. 

Bodycon — short for "body-conscious" — is a form-fitting style that will show off all your curves. A bodycon dress is a beautiful and flattering choice, especially for more formal settings. By adding a pair of boots, you can maintain comfort while still being on the best-dressed list.

You can find a bodycon dress in any sleeve length, but for winter and fall, you'll likely want long sleeves. A black or gray bodycon dress pairs beautifully with neutral ankle boots. Complete this look with a stunning necklace and earrings to set your outfit over the top.

Spring and Summer Dresses

As the snow starts to melt and temperatures climb, it's time to switch up the wardrobe for shorter sleeves and lighter materials. While soft and heavy fabrics are suitable for colder seasons, lightweight materials like linen, cotton and rayon will give your skin some room to breathe when the weather warms up.

To stay cool and fashionable in the warmer seasons, check out the best boots for dresses in warmer weather below.

1. Sundress and Cowboy Boots

Create a trendy country look this summer by pairing a charming sundress with some cowboy boots. When it comes to color and pattern, your choices are nearly endless! A white sundress paired with brown cowboy boots offers a classic romantic look, and floral sundresses can be an elegant option for the spring and summer seasons. 

Of course, no outfit would be complete without accessories. Feel free to add a couple of bracelets and a cowgirl hat. This look is ideal for a summer photo shoot or for a rustic-style wedding.

2. T-Shirt Dress and Combat Boots

Opting for a cute and casual look this spring? A t-shirt dress and combat boots may be the ideal outfit for you. You can find T-shirt dresses in a wide variety of colors and patterns, so pick one that reflects your unique sense of style. If you need some inspiration, here are three outfit ideas to get you started:

  • A black and white striped T-shirt dress with black or white combat boots
  • A plain white or gray T-shirt dress with brown combat boots
  • A mustard or army green T-shirt dress with black combat boots

Feel free to try out any colors or patterns that reflect your personal style. You can even start out with a basic dress and personalize it with pins, embroidery or patches. Once you've found your perfect dress, a color-coordinated handbag is a great way to accessorize this casual outfit.

3. Cocktail Dress and Wedges

Looking for a stylish and elegant outfit for the warmer seasons? A beautiful set of wedge boots pairs wonderfully with a short-sleeved or sleeveless cocktail dress. Whether it's Easter, a wedding or an evening out with friends, this gorgeous outfit can accommodate a variety of spring and summer settings.

Floral patterns and soft pastel colors are lovely options for spring and summer, and we highly recommend embracing them with your cocktail dress. Add a pair of brown or gray wedge boots to the mix, then feel free to accessorize with some jewelry to complete the look.

Shop Dresses and Boots Online at Perfectly Priscilla

Looking for some trendy boots and dresses to spruce up your wardrobe this season? At Perfectly Priscilla, we believe that every woman deserves to feel confident and beautiful — and with the right outfit to accent her unique style, she's unstoppable. 

Our gorgeous selection of plus-sized women's clothing will keep you comfortable and stylish year-round. No matter the season or style you're shopping for, you can find amazing outfits through our online boutique. Browse our store to find the perfect dress or pair of boots to accommodate any season or occasion. 

If you need help selecting the perfect outfit or have any questions regarding our products, contact us at any time!

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