Shoes can be the trickiest part of an outfit to get right, and since I know women absolutely love shoes and boots, I want to help make this easier for you. In addition to the confusion shoes present, there are several new boots to add into your fall/winter wardrobe mix. Here are some ways to wear them all!

Over the knee boots

Over-the-knee (no, not thigh high) boots aren’t everyone’s cup of tea, but if you’ve been wearing riding boots for years and feel like you need a change, they’re great. They’re truly best with skinny jeans and leggings for off hours, but they can also be cute with a short skirt that shows just a sliver of leg for going out or a casual weekend look. You might think these boots would be great with a long skirt, but I feel like that’s just a little outdated. And why would you want to hide your cool, new boots?

Booties (a.k.a. ankle boots)

Booties, (bottom middle and right photos) have been on the scene for several years now and don’t show signs of going anywhere! Whether low heeled or high heeled, suede and fringe are two very big “bootie” trends this season. If you have trouble finding tall boots to fit your calves, these are a sure bet for you!

Depending on your personal style, booties can be worn with full-length pants, cropped and ankle pants and even skirts and dresses.

Chelsea Boots

I am in LOVE with my new Chelsea boots! (Yep, those are my actual boots at the bottom left of the photo.) I’m even planning on wearing them with wide legged trousers! Trousers don’t usually work with flats, but because I have long legs and the boots are so pointy, it works! Hem your leggings and skinny jeans right to the top of the boots for the most modern look. And I almost forgot…for a fashion forward business casual pairing, wear your Chelsea boots with a pencil skirt and sweater!

Knee boots

The classic knee or “tall boots” are a classic! And with Colorado’s cold, winter climate, they’re a must have! Although a classic, even knee boots change a bit every few years. The most current style hits very close to the knee versus simply ending at the wide part of your calf.

Low heeled and flat riding boots are the perfect option choice for leggings and skinny jeans. And while the low heel version isn’t perfect with most flared skirt, they work quite well with pencil skirts.

Heeled boots are best with pants worn on the outside and most skirts. With a dress, heeled boots create an unexpected, edgy mood!

Have visited your “shoe closet” and made your shopping list? I’m seeing a lot of sales in the stores, so be sure to shop for your new boots soon while your favorite styles in your size are in stock.