How to Wear Dresses with Boots
To wear dresses with boots, make sure the styles match. For example, brown ankle boots would work well with a light, flowing dress, but motorcycle boots would not. In addition, pay attention to how formal the boots are. Sleek, thigh-high boots tend to be very formal, so you may want to wear chunky ankle boots if you are going somewhere casual. If it's cold outside, opt for a pair of wool tights or leggings and leather riding boots. In warm weather, flat ankle boots and denim shorts may be a better combination.
Match the boots with the style of the dress. Try to pair the style of boots with the style of dress you're wearing. For example, a pair of chunky, motorcycle boots wouldn't work well with a light, flowing dress, but they would work well with a leather dress. Also, a pair of brown ankle boots wouldn't look good with a leather dress, but they would work well with a light, flowing dress. Wear boots that are formal or casual enough for the occasion. Along with matching the style of the boots with the dress, choose the right boots for the occasion. A pair of sleek, thigh-high boots might look good with a black dress, but it wouldn't be appropriate for a fairly casual occasion. Instead, opt for a pair of chunky, ankle boots for a casual occasion. Make a black dress appear more casual and edgy by wearing a pair of chunky, leather boots with it. Wear high-heeled boots with the same black dress to dress the outfit up. Decide on tights or bare legs. Whether you wear tights or not largely depends on the weather. It is better to wear tights or leggings with your boots if the weather is cold, especially if the dress or short. For a warm, casual occasion, opt for a bare leg look. For cold weather, wear a pair of wool tights with long, leather riding boots. Wear a pair of flat ankle boots with denim shorts for warm weather. Allow a few inches between the boot and dress. There are exceptions, but typically, you should leave at least a few inches of skin exposed between the boots and the hemline of the dress. Leaving at least a few inches exposed is usually more flattering. Even if you are wearing a long dress, try to wear boots that leave a “peek” of your legs. Pair slouch boots with a fitted dress. Slouch boots are ankle boots that don't fit tightly around the ankle. Pairing slouch boots with a short, fitted dress is a good way to keep the look laid-back. It is also a good way to make your legs appear slimmer. Wear black tights for an extra slimming look. Make the look edgier with a flowing dress. This look is one exception to the guideline of pairing the boots with the style of dress. Wearing ankle boots with a flowing dress is a good way to add juxtaposition and a bit of edge to the style. Choosing motorcycle boots, however, may be too much of a juxtaposition. Wear open-toe boots with a frock dress. A frock dress is a dress that was popular in the 1950s and is typically looser fitting except around the waist. Pair a mid-length frock with a pair of open-toe boots. The open-toe boots should be ankle length. The open-toe boots are a great way to add a touch of modern style to a retro look. Wear a floral frock dress with open-toe boots that match one of the colors in the dress. Choose a short dress with over-the-knee boots. A short dress with over-the-knee boots is a very cute and common choice. You can wear a tight, fitted dress, or a loose, short dress. Suede boots look good with a casual dress. Leather or pleather boots look better for a dress that is meant to be worn on a night out. Wear a short, flowing lace dress with a pair of brown over-the-knee boots. Pair a knee-length dress with riding boots. Choose a loose, knee-length dress with a pair of tall riding boots. A cream-colored dress with a pair of light brown riding boots would be a good option for this look. This combination is casual, but elegant and can be worn at almost any time of the year. Don’t show any skin between the dress and boots. This is the exception to showing skin between the dress and boots. Choose a pair of thigh-length boots of any type. Suede, velvet, and leather boots are a few options. Make sure the boots fit tightly around your legs. For more casual boots, wear a loose, floral dress. Wear a tight dress with high-heeled boots for a nighttime look. 
Match the boots with the style of the dress. Wear boots that are formal or casual enough for the occasion. Decide on tights or bare legs. Allow a few inches between the boot and dress. Pair slouch boots with a fitted dress. Make the look edgier with a flowing dress. Wear open-toe boots with a frock dress. Choose a short dress with over-the-knee boots. Pair a knee-length dress with riding boots. Don’t show any skin between the dress and boots. 