When I hear the word ‘boots,’ I immediately think of the more utilitarian snow boots that are perfect companions for the cold, snowy, slushy days ahead in Kansas City. But this winter season, boots are as much about making a fashion statement as they are about functionality. Footwear designers definitely have our feet (and legs) covered, but the many choices can be confusing.

Stylish mannequins posing in window displays sport boot trends from over-the-knee and knee-high boots to the 70s stacked heel boot, ankle boots and slouchy boot. There are riding or equestrian boots, biker boots, the lace-up boot and the harness boot. And there are booties (sometimes called shooties: shoes + boots) and of course, the all-American urban cowboy boot.

So how to know which boots are right for you?

Honestly, I feel a little clumsy when selecting a boot style for myself. I’m more of a pump wearer—I’m confident when searching for the perfect black patent pump. I know what looks good on my foot, and my requirements in fit and height. I can also easily discriminate between various toe shapes, straps and heels.

Many of my clients feel this pang of insecurity, too, when it comes to trying a new fashion trend. There is an inevitable period of adjustment and getting comfortable with a new look and integrating it into your own personal style.

What helps my comfort level when exploring new trends is seeing the look in fashion magazines, in local retailers’ displays and noticing how someone puts the look together. Then I visualize myself creating an outfit with what I have in my closet or use those mental pictures when shopping.

The over-the-knee boot trend has been the most influential boot style on this year’s fashion runways. Worn correctly, over-the-knee boots add an element of sophistication to an outfit. They ooze a sense of power along with sexuality. Worn with an oversized sweater that might drape longer in the back or worn with a sheath type dress, keeping the line monochromatic from shoulders to toes, is a chic way to strut this boot style.

Riding boots are supremely popular. They impart a classic look, and for whatever reasons, “classic” always works. The sleek boots look especially sharp, of course, when worn with riding pants but most of us probably tuck in our jeans, ponte knit pants or leggings into boots. The riding boot pairs well with flirty skirts, too, and is versatile thanks to its flat nature and neutral appeal, usually brown or black.

Another hot look this season is the fur-trimmed boot. Real fur, faux fur and shearling trim add a hint of fluff around the top or cuff of a boot. Besides being very en vogue, these boots definitely keep legs warm and toes toasty.

This season’s boots are made with other contemporary materials that make selecting a style even more difficult. Think leather, patent and reptile skins and suede, satin and even lace. The choice of material usually is a personal preference.

If you wonder how many boots a person actually needs, I might suggest a minimum of two: a dressy pair and a more casual pair. No matter your heel preference, there are plenty of options from flat to stiletto. If height and comfort are paramount, the wedge heel gives added support while still being fashionable.

Embrace this winter’s chill knowing there is a boot out there for you and your every occasion. Take a friend when shopping for boots or hire a stylist to help you embrace the fashionable footwear that will have you stepping out in cozy style this season.