December 13, 2024
10 Ways to Wear Dresses with Boots
Looking for the perfect transitional footwear to carry you through changing seasons? Boots are an all-time favorite for a reason — they’re some of the most versatile shoes you can own. With a variety of designs, like heeled boots, suede booties and classic Chelseas, a good pair can completely transform how you style your favorite dresses.
In this guide, we’ve put together the 10 best boots and dress combinations to help you elevate your style and inspire your outfits — no matter the season.
1. Floral Midi Dress with Chunky Heeled Boots
If you were to ask our stylists what the best dresses to pair with boots are, floral midis would be at the top of the list. A pair of chunky heeled boots with a romantic midi dress is a classic combination! It works thanks to its mix of soft and strong styles, the flowy fabric pairing beautifully with the structured vibe of chunky heels.
Styling tip: Let the florals take center stage by choosing boots in neutral tones like black, tan or soft cream. If the weather calls for a layer, a pair of tights and a cropped denim or leather jacket create a chic look without outshining the dress.
2. Denim Shirt Dress with Sleek Ankle Boots
Looking for an outfit that’s always in style? Pair ankle boots with dresses made of denim. Whether you’re headed to the office or out for a coffee date, denim dresses with ankle boots are flattering on everyone. It’s an easy combination that you can throw on quickly and feel instantly put together.
Styling tip: Go with ankle boots in black, white or rich brown to keep the look natural and cohesive. If you want to add some texture, a leather belt at the waist or a crossbody bag can elevate the look without overcomplicating it.
3. Knit Sweater Dress with Wedge Boots
Have a knit sweater dress hanging in your closet and don’t know how to style it? Pair it with wedge booties for a cozy, sweater-weather outfit that’s equal parts warm and stylish. The knit dress with booties combo works because the height of the wedges gives the dress a classy and sophisticated vibe yet keeps the outfit comfortable enough for all-day wear.
Styling tip: For the perfect day-to-night transition, stick to wedge booties in neutral tones like taupe, black or brown. Throw on a belt at the waist to add a little shape, or leave the dress loose for a more relaxed fit.
4. Boho-Chic Maxi Dress with Suede Boots
If the weather calls for a longer dress but you still want to bring a little free-spirited energy to your look, pair a boho maxi dress with suede boots. It’s one of those combinations that always look good with the flowing fabric blending beautifully with the smooth texture of suede boots.
Styling tip: Opt for boots in earthy tones like tan or rust to complement the dress’s natural feel without competing with it. If it's cooler out, a denim or jacket works well for a laid-back vibe.
5. Tailored Blazer & Skirt with Heeled Booties
Need an outfit that can take you from business to romance? A blazer and skirt with heeled booties can help you make a seamless transition from the office to date night. This combo gives you plenty of room to mix and match. For example, a structured blazer goes great with a pencil skirt, while an A-line skirt can soften the outfit if you’re looking for a more relaxed feel.
Styling tip: For a more formal style, go for booties in black, camel or beige, or add a pop of color for something more modern. To pull it all together, add a belt or an elegant clutch with gold or silver accents.
6. A-Line Dress with Chelsea Boots
One of the most comfortable boots to wear with dresses is Chelsea boots, which go exceptionally well with A-line styles. Chelsea boots are one of the most popular boots on the market — and for good reason. They’re trendy, easy to slip on and sturdy enough to make them comfortable to wear all day long. When matched with an A-line dress, the combination feels casual yet put together.
Styling tip: For a classic look, go with boots in black or brown to complement the flow of the dress. If you’re aiming for something more playful, try boots in a bold color or a unique finish like two-toned leather. On cooler days, layer with a puffer jacket or an oversized cardigan to keep the outfit warm and chic.
7. Lace Dress with Minimalist Leather Boots
Want something romantic with a twist? Lace dresses with boots work bring a unique mix of delicate and edgy elements in a way that feels fresh and natural. Minimalist leather booties are the perfect boots to go with dresses with intricate details like lace because they’re stylish but don’t overwhelm the outfit.
Styling tip: Ankle boots pair nicely with shorter lace dresses, while mid-calf styles bring a bit more drama to the outfit. If it’s cooler outside, consider layering with your favorite jacket or a soft wrap for cozy comfort on the go.
8. Corduroy Dress with Weather-Resistant Rain Boots
Rainy days don’t have to mean settling for a dull outfit! A burgundy or taupe corduroy dress with weather-resistant boots can brighten things up. We’re big fans of this combination because who doesn’t like to feel cozy? The soft texture of corduroy gives the outfit a comfy feel, while the boots keep you dry and ready for whatever the day throws at you.
Styling tip: For boots that’ll go with everything corduroy, opt for boots in earthy tones like brown, black or olive. A shorter dress pairs well with ankle boots, while taller boots work great with midi lengths if you need some extra warmth and coverage.
9. Wrap Dress with Elegant Wedge Booties
For an ever-flattering and easy-to-style outfit, combine a flowy wrap dress with elegant wedge booties. The beauty of wrap dresses is that they naturally highlight the waist and legs without being revealing, while the wedge booties add just the right amount of height and structure to round out the look.
Styling tip: Choose wedge booties in neutral shades like black or beige for a versatile look that can be paired with any dress. If it’s cooler outside, layer with a cropped jacket or a lightweight coat for extra warmth and style.
10. Bodycon Dress with Heeled Boots
Boots might not be the first shoe that comes to mind when you think of curve-hugging bodycons, but they make a show-stopping pair! The bodycon’s fitted shape is perfect for when you want a bold, confident outfit, and when you combine it with heeled booties, you give the look some height and elegance — without sacrificing comfort.
Styling tip: Wedge booties in classic tones like black or brown work well for a clean look, or go bold with a deep red or metallic finish if you’re feeling playful. Throw on a relaxed blazer or a leather jacket to balance out the dress’s fitted shape and you’ve got an outfit that’s cool, confident and ready for anything.
The Do’s and Don’ts of Wearing Dresses with Boots
Boots and dresses are a combination that can easily go from effortlessly elegant to clumsy and mismatched if the details don’t come together. Here are a few do’s and don’ts to help you get the look just right:
Do’s
- Pair ankle boots with a dress shorter than or at the knee to balance out the look.
- Stick to neutral-toned boots like black, brown or taupe for versatile styling.
- Play with textures to give your outfit different vibes.
- Add layers like a jacket or scarf to tie the outfit together.
- Match the vibe: casual boots with flowy dresses, sleek styles with fitted dresses.
- Let your boots take center stage with simple, solid-colored dresses.
Don’ts
- Don’t overcomplicate it. Keep accessories minimal so the outfit doesn’t feel cluttered.
- Don’t pair heavy, chunky boots with delicate fabrics. Otherwise, you might throw off the balance.
- Don’t let boots and long dresses compete. If the hem is too low, go for ankle styles.
- Don’t forget proportions. Thicker fabrics work better with sturdier boots.
- Don’t ignore the season. Opt for leather or weatherproof boots for winter and lighter styles for warmer days.
- Don’t wear boots that clash with the dress’s vibe. Keep it cohesive!
Wear TOMS. Wear Good.
With so many options for booties to wear with dresses, you’ll find endless ways to create your own styles. That’s why you need a few dedicated pairs you’ll reach for season after season.
TOMS boots are made to move with you, wherever your day takes you. From everyday Chelsea boots to elegant wedges, our women’s boots are designed to feel as good as they look.
When you wear TOMS, you’re also part of something bigger. We put a third of our profits toward grassroots efforts that drive meaningful change, so every step you take helps make a difference. Want to learn more? Read about our impact.