How to Wear Boots with Dresses

It’s time to get excited about cooler weather and wearing your favorite fall boots. Whether you’re looking for new ways to style a tried and true pair or you’re outfitting something new, one question remains: How to wear boots with dresses?

There are a few do’s and don’ts when it comes to pairing boots with dresses or skirts and if you follow our tips you’ll look runway ready all autumn long!

If you have always wanted to wear boots with dresses but weren’t sure where to start, our pairing tips can help you look and feel your best as you try a new look!

Table of Contents


  • Pair chunky boots with shorter dresses
  • Pair sleek, heeled boots with structured dresses
  • Keep the dress, boots and tights in the same color family
  • Contrast feminine with rustic or utilitarian looks
  • Wear midi dresses with ankle boots
  • Pair short ankle boots with maxi dresses
When paired well, boots and dresses can really complement each other! Just take note of how you’re pairing materials, colors and themes. A sleek, pointed toe croc faux leather boot looks chic with fitted bodycon dress. This same boot, however, could look awkward with a relaxed cotton midi or linen dress. While you do want to play with contrast (tough with feminine for example), remember to follow an aesthetic that is visually cohesive. Some dresses and boots outfits have harmony while other combinations are major fashion faux pas.


  • Don’t wear ankle boots with dresses that end at the widest part of the calf
  • Don’t wear loose-fitting leggings with your dress and boots
  • Don’t pair sleek or pointy boots with way-too-casual dresses
  • Don’t pair chunky combat boots with extra long maxi dresses
First and foremost, dress for your body type! Some of the do’s and don’ts may work on some women and not work for others. Petite women generally want to avoid dress lengths and boot heights that visually shorten their legs, for example. A dress that ends at the widest part of the calf when paired with an ankle boot may not be the best choice for a petite or pear-shaped woman. You’ll also want to avoid ill-fitting tights or leggings that can make a dress, boots and tights combo look awkward! Also, while you want to have fun with contrast, some combinations simply don’t pair well. Loose, casual dresses generally don’t look right with dressy or pointy boots while chunky combat boots may look sloppy with an extra long maxi. If you’re unsure which style of dress to wear with boots, here are a few combinations that work on most people!

Dresses and Boots That Pair Well

  • Knee high boots and fitted sweater dresses
  • Ankle boots and flirty skater dresses or minis
  • Sleek heeled boots and tailored dresses or shirt dresses
  • Lace-up or combat boots and shorter tea dresses
  • Western boots and linen or denim dresses

Knee High Boots with a Sweater Dress

Pull off a fashion-forward look with knee high boots and a sweater dress. This look works best with fitted, shorter sweater dresses. Show a little leg or keep warm with tights! Consider color and material to enhance the outfit. A rustic brown faux suede boot gives a basic black sweater dress a fall-ready update, while a black faux leather pair adds a little edge to a classic cable knit dress. Have fun playing with contrast! Juxtapose feminine with rustic or soft with utilitarian, for example.

Ankle Boots with a Skater Dress

Bring the classic summer look of a skater dress into fall with pretty ankle boots. This shorter dress pairs well with feminine booties that elongate your legs! For chilly autumn days, layer up with a chic coat and tights. Color is key! For an elegant look, reach for a black skater or tennis dress, black or gray tights and simple faux leather booties. Add a pop of fall color with a red or gold coat.

Heeled Boots with Tailored Dresses

Head to the office in chic fall style with a tailored shirt dress and a pair of sleek heeled boots. The heeled boot is autumn’s version of the pump! Elevate your work ensemble in a sleek heeled bootie in black. Pair it with a classic print dress like argyle or houndstooth. Tweed also brings instant chicness for an office-ready outfit that will show everyone who’s boss.

Combat Boots with Floral Tea Dresses

The 90s grunge look always packs a style punch! Bring this edgy aesthetic to your fall wardrobe by pairing a pretty, feminine floral dress with a pair of chunky lace-up boots! The contrast of florals and utilitarian vibes instantly draws attention. For busy fall Saturdays of shopping, dog-walking or other happenings, you’ll stay comfortable and stylish in a dress and combat boots.

Western Boots with Linen or Denim Dresses

The western look is in this season! Bring casual, rustic vibes to your outfit with a pair of western booties and a denim or linen dress. A long ruffled denim skirt is also a great pairing option! Brown faux leather boots with a Western flair pair perfectly with a casual linen or denim dress. Keep cut and color in mind! A rich camel brown bootie and a white, relaxed linen dress keeps your look low key while a white Western bootie with a fit and flare denim dress brings a little country glam! Sleek faux leather black boots are also a great way to contrast rustic with chic. Complete your Lonestar look with southwestern-inspired jewelry and a faux leather tote.

Style Tips

There are plenty of ways to pair boots with dresses. Following a few key fashion tips gives you an advantage that makes you look like a style pro! Just remember to follow a theme when choosing your dress and boots combination. Sleek boots or booties work best with fitted or structured dresses while chunkier boots look best with shorter or mid-length feminine styles. Keep the day’s activities in mind too! Stay comfortable in flat boots and a relaxed midi dress for hectic days or elevate a casual fabric like linen or denim with a dressier heeled boot and waist belt. Take some creative liberty by layering bold jewelry or outerwear to make each look all yours. Find many unique ways to wear your favorite boots, skirts and dresses.

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