The short answer is yes, absolutely! Boots and dresses were practically made for one another, and styling them together can make an entire outfit look fabulous. This classic couple can be worn all year round for an easy and stylish go-to look that will take you just about anywhere. But, there are so many kinds of boots and styles of women’s dresses that it can be overwhelming to figure out how to create the right outfit. Luckily, we’ve made a handy little guide that covers the basic styles of dresses and what boots look best with them so that you can choose what works best for you.
Mini dresses may feel a little nostalgic for the ’70s, but they are cute, versatile, and look amazing with a good pair of boots. Even if you veer towards modesty, wearing a mini dress over leggings, tights, shorts, or jeans is a great way to rock this look without baring skin. Because mini dresses tend to hit mid-thigh, they look particularly great when worn with a pair of high-cut boots. Consider mid-calf to knee-high riding boots with these dresses, as they break up the legs visually but also give them a streamlined and longer look. Mini dresses also look spectacular with thigh-high boots that go over your knees. This cute and playful look makes a statement and can be worn all year round if layered correctly. Although mini dresses also look good with ankle boots, they look best with higher-cut boots. Because of all the space to show off your legs when wearing a mini skirt, this is the best opportunity to be wearing more ornate, decorative, or statement boot styles, such as Western or lace-up fronts and bold colors.
Midi dresses are another winner when wearing dresses with boots. There are few boots that won’t go with this versatile style of dress. This mid-shin length dress looks great with just about any boot, but it’s best to go for ankle-length boots or go all the way thigh-high. This is because midi dresses end at the shin, and you want to have your footwear end above or below the hemline of your dress to look the most flattering. Another strong pairing is to wear a pair of slouchy knee-high boots, especially when the boots match the shade or color of your dress. Midi dresses look fantastic when worn with heeled boots, especially a block heel, but they will also look great worn with flats. Even wearing some Chelsea-style flat boots will give your dress a more down-to-earth look and will let your dress snazz up your boots.
Maxi dresses are often floaty and flowy, and your choice of boots should balance and match this look. Maxi dresses are wonderful to wear year-round when layered well and worn with a good pair of boots. If you’re styling a maxi dress that has leg slits, then don’t be shy to rock some high-cut boots as a way to add a little extra dimension that peeks out from beneath the dress. For closed dresses, opt for pointed-toe heeled or flat boots. The pointed toe and the height of heels will help to elongate your frame and help you take your maxi dress to the max. While wearing heavy leather boots looks great for most of the year with a maxi dress, in the warmer seasons, when you want to don light and flowy cotton maxi dresses, it’s best to wear boots that are lighter in color and material. A nice cream or white pair of suede booties will look amazing with your favorite lightweight summer dress.
Shirt dresses and shift style dresses are like mini dresses in length but tend to be more casual in style. Looser fitting, relaxed, and somewhat androgynous, these cool dress styles look fabulous with the right kind of boots. Shirt dresses look especially stylish with thigh-high or knee-high boots. This is a fantastic go-to look to layer all year round by wearing a shirt dress under a sweater and over a pair of wool tights and high-cut boots for a great colder weather outfit.
Shift dresses pair well with just about any style of boot. These loose-fitting and boyish dresses look good with a boot that balances the shape of the shift dress. We love shift dresses worn with anything from thigh-high to ankle bootie and everything in between. Dress up a shift dress with a pair of heeled knee-high boots. Or, dress it down with a pair of flat ankle boots or Chelsea-style boots for a laid-back daytime look.
Though we’ve covered all the basics, it’s good to look at some more general styling tips for wearing dresses with boots. Firstly, match the style of boots with the style of the dress. For example, a pair of chunky hiking-style black boots wouldn’t pair so well with a light and flowing summer dress. But, they would look great with a fitted little black dress.
Also, a pair of slouchy suede boots would look much better with a cute flowy shift dress than with a body-con style dress. When pairing boots and dresses, it’s also important to pair according to the occasion. Your Western-style boots may look great for a backyard barbecue with your shirt dress, but you’ll probably want to wear a pair of black riding boots and a sweater dress for a candlelit dinner out. Boots can also dress up or dress down an outfit, depending on how you style them.
Boots and dresses are truly a match made in heaven. So grab your dresses and pull out your boot collection to start mixing and matching to see what looks and feels best for you.