A friend of mine recently bought a pair of boots from J Crew.  They are classic and elegant and timeless, the kind of boots that will always be in style.  She was excited about them and how they’d go with everything in her closet. 

One problem though:  The classic boots gave her some severe cankles.  Sorry…but there’s really just not another word for it.  The boots were very pretty and my friend’s legs were very pretty, but there was just something about the lack of shape around the ankle of the boot that made her lean runner’s legs look shorter and wider.   The result was a boot that added weight to the entire silhouette of any outfit she tried to create.

In order to help my friend avoid re-ordering a pair of weird, barrel shaped boots, I began a long period of research into the anatomy of boots.  The style she had originally picked out was a cross between an engineer boot and a stovepipe boot, which generally  are a little bit larger through the shaft (i.e. the tall part of the boot that goes up your leg).  These wider, slouchier shapes are actually very in style right now.  Pair them with some thick, knee-high boot socks and super-skinny jeans  and you will have mastered the look (on the bottom half at least).  The only problem (the one that my friend encountered) is that unless you are a statuesque, perfectly proportioned woman à  la Gwyneth Paltrow (who wears engineer boots like it’s her job), you might wind up looking like you are wearing barrels on your ankles.  This holds true for women who have very thin calves, women with athletic calves, and curvier ladies with thicker calves.  This style of shoe toys with proportion in a way that makes the average boot-wearer balk and reach for the return slip; you basically need some freakishly good genes to pull this barrel boot thing off.

So, if you are searching for new boots to replace the awkward barrel boots you may have accidentally purchased, here are things to consider while you shop.

1)  Boots have lots and lots of different parts.  If you want a boot that slims the ankle, you’ll need to look at the intersection between the vamp, shaft, and heel counter.  The vamp is the portion that covers the top of your foot.  The shaft is the part that goes up your leg and is often decorative.  The heel counter is the cubby-hole like portion inside the boot that holds onto your heel and prevents your foot from slipping around. With boots, a little slipping is normal at first and will decrease as the leather molds to your foot.

Note: The boots on the right are the very classy J. Crew boots…cute and wonderful, but not especially flattering through the ankle area.  The boots on the left are a Bohemian inspired cowgirl boot from Lucchese…see the difference with placement of stitching and the way the contour of the boot forms? 

2) Those cute new ankle booties you just bought?  If they cup underneath  your ankle bone, they are comprised of a vamp and heel counter, but lack a shaft. This same shape will be replicated in a boot that will curve in around your ankle.

3) Boots are made of several different pieces of leather.  If you’ve ever seen a dress pattern, you understand that the way the dress forms against your body fully depends on the cut of the fabric.  Similarly, the cut of the leather that comprises the shaft of the boot will make a difference on how the boot forms to your leg.  If the boot is cut straight up and down, why should you expect it to curve with your ankle? Calf skimming boots will make your legs look longer, since they closely follow the contour of the body and do not add bulk.

4)  Measure your calf with a tape measure.  You can get away with the shaft being about 1/4 too wide or ½ too tight.  The boot will stretch about that much, but not a whole lot more from normal wear.  Ideally, the boot shaft will be flush with your calf.  If you have athletic calves, you can order boots (particularly the handmade kinds, like boots from Lucchese and Corral) that are specifically cut to fit your unique calf shape.

Below are some boots that I know are either handmade (and can be custom fit to your leg) or are cut to fit the calf particularly well.

Enjoy!