There shouldn’t be more than half an inch between your leg and boot, but boots also shouldn’t feel constricting. If you have trouble fitting your calves into boots, you might try finding a boot specialist to custom fit them for you.

Yup! I do it all the time. It depends whether you're planning on wearing them over or tucked in. It may be slightly harder to keep them tucked in with sweatpants, especially if they don't extend over your ankle or up to your calf. But yes, go for it!

Choose chukka boots, also called bucks or turf boots, to go with anything from jeans and a t-shirt to slim cuffed pants and a solid button-down.Combat or motorcycle boots can be worn with dark clothes and leather for an edgier style.

If you wear heeled boots with a fuller dress or skirt, it can fall just above the top of the boot. If your dress is more form-fitting, it should come to a few inches above the boot or knee.

Stick with neutral color boots (black, brown, or gray) to wear them with any outfit. A good rule for both men and women is to match your boot color with your belt color, too, if you’re wearing one. In general, wear brown with brown and black with black.

Wear boots under wider pant legs. Choose narrow, smooth boots without a lot of extra bulk like buckles or straps if you want to wear pants over them. Bootcut jeans and pants are made for this. They should be wide enough to easily fit over your boots, and skim the top of where your foot is.

Choose ankle or knee-high boots like cowboy boots or riding boots to tuck pants or jeans into. Slouch boots are often roomier if you’re having trouble fitting your pants under boots. Wear skinny or narrow fit pants for this look.

To make boots the focal point of your outfit, try out knee-high boots in a bright color like red or purple, cowboy boots with colorful embroidery, or a high stiletto-heel boot. Make sure you wear more neutral and solid color clothing when you opt for a statement boot.

Expert Trick: If you have short legs, try wearing a mini skirt with ankle boots to create a longer leg line. However, avoid wearing ankle boots with a knee-length dress, which will make you look shorter. If you have long legs, you can pair your ankle boots with almost any length dress except for a mini, because the proportion will be off.

Kathi Burns is an Image Consultant, board certified Professional Organizer (CPO), and the Founder of addSpace To Your Life!, her consulting business with a mission to empower people to master their environment and personal image by assisting them in taking control, making change and organizing their lives. Kathi has over 16 years of organizing experience and her work has been featured on Better Homes and Gardens, NBC News, Good Morning America, and Entrepreneur. She has a BS in Communication from Ohio University.

Boots are very versatile and come in many different styles and heights, but it can be difficult to choose what type of boot works best with an outfit. Learn how to choose a pair of boots that is right for the occasion, pairs well with dressy or casual outfits, and is flattering to your body.

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