Boot season is upon us here in Minnesota, and over the past few weeks I've gotten several requests for boot-buying guidance. I've already written a post about how to track down your perfect pair of boots, and followed it up with my specialty size resource bonanza for those who struggle to find boots that fit properly. But the pressing boot question that remains unanswered is this: What styles of boot are the most essential and versatile?

The complete boot wardrobe

Every boot-wearing woman's needs, tastes, and styles will be different, so it's a bit ridiculous to propose a "complete" boot wardrobe. Just as it's a bit ridiculous to declare that every stylish woman MUST own a white button-down and black pencil skirt. However, there are several types of boot that are just classic and versatile enough to merit near-universal recommendation. At least, in my opinion.

And - in order from most to least important - they are:

Sleek tall flat boots

John Fluevog Heidi

I don't care if they're riding boots, moto boots, or something else entirely. They need to be relatively plain, a neutral color, flat or nearly flat, and comfortable as all get-out. Combat boots, moccasin boots, brightly colored boots, cowgirls, and embellished boots need not apply. These are your workhorse, go-with-everything flat boots.

Classic tall heeled boots


Calvin Klein Selma

It's rather astonishing how difficult it can be to find an unadorned, classically styled pair of tall, heeled boots. This CK pair is gorgeous and definitely fits the bill, but that's a hefty heel, there, and if they weren't 40% off, they'd be pretty spendy. Yet despite the challenge, I feel that keeping your eyes peeled for a relatively hardware-free pair of plain, beautifully-designed, zip-up, tall, heeled boots is both wise and prudent. Because, along with your flat boots, these will go with nearly everything you own. It may take a while to track 'em down, but they'll be worth the wait.

Tough boots


Alice + Olivia for Payless Madison (no longer for sale)

HERE. Here is where you can indulge your desire to wear weathered leather, loads of buckles, a big old wedge, or any other feature that makes a boot seem tough and edgy. Your tough boots can be tall, short, or in-between. They can be any color or material you like. Just be sure they make you feel like a total rock star.

Fun or costume-y boots

Frye Harness 12R

Whether you want cowgirl boots, super modern spacewoman boots, granny boots, or some other style that will only suit 15% to 20% of your wardrobe, this final pair on the list indulges your sartorial alter ego. As with your tough boots, your fun pair can be any color, shape, material, and height that suits you.

Optional choices include: A colorful tall or short boot, booties, and doubles of any of the above choices in alternate colors or materials. Of course, this list omits snow boots, rain boots, and other practical choices since those are even more personal and specific. This list is a highly generalized group of fashion boots only, and isn't meant to cover anything weather- or profession-related.

And honestly if you only ever located a fabulous pair of tall, flat boots that fit and suit your personal style, I'm pretty sure you'd be golden. So if this post makes you feel overwhelmed and poor, don't despair! Just start scouring eBay for your perfect flat boots, and worry about the rest later. If ever.

Are you a boot lover? What styles of boots do you consider to be essential? Most versatile? Do you own boots that fit into these categories? Any others you'd add?  

Sally McGraw is the author of Already Pretty, a daily blog about the intersection of style and body image.

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