How To Wear Tall Boots

Oct 9 2013

by Tina Adams

Tina, here.

Today it’s all about tall boots.

Tall boots remain an easy, classic choice to elevate any look.

Riding Boot Perfection from Taigan.

For more on how to wear tall boots, keep reading.

Let’s start with the rules. Because you know there had to be rules!

Great color combo. (via

In general, when buying tall boots look for:

Very little hardware, harnesses, or buckles. No reason to shackle your ankles and legs with weights.

Brown boots, if you can only have one color. So much softer with other colors than black boots.

The shaft should fit your calf. No stuffed sausages and no swimming bird legs!

So how do you wear tall boots? With everything. It’s hard to mess up boots.

A-line skirt and brown boots … sweet! (via ish and chi)

With an a-line skirt, just make sure there is a little space of skin between the skirt and the boots to keep it from being heavy.

With tall boots you don’t need to wear tights unless it’s cold and you just want to.

Fall outfit: Plaid Tunic Dress + Black Patterned Tights + Brown Boots
Plaid dress, black tights and whiskey boots. Great combo! (via sezane)

The Great Kate in riding boots – note the socks peeking out on top. (via lordofhahn)

Ralph Lauren Fall 2003, and it still looks good 10 years later. (via

If your skirt happens to be longer, just make sure it is bias-cut, as above, to create movement.

When wearing knee boots over pants, try wearing actual pants, and not leggings. Like skinny jeans or a stretchy material made from a substantial fabric.

That’s adorbs Olivia Palermo, in tall boots over pants. Got that? Pants, not leggings. You have to look closely to see that she’s wearing an actual pant. (via how to be lovely)
Casual style

With jeans. (I endorse skinny jeans for this purpose!) I also love her belted sweater. Such a great way to tame the bulk. (via cardigansforsale via pinterest)

Riding boots with cords. Black and brown is such a rich combination. (via equestrianstylist)

With white jeans. Yes, wear your white jeans all winter long with warm colors like brown and camel. (via allthingselegant)

Dress too short? Just add tights in same color to create one line.

Match the color of the skirt or dress to the tights for one long line. Bonus points if your boots match, too. (via leslie’s corner)

And if you buy knee boots that fit your calves tightly, you can make them do double-duty and wear under your pants! Cost per wear just got better!

What about scrunchy boots?


If you’re young, go for it. If you’re past your 20’s (and I’m not saying you’re not young!), approach scrunchy boots with caution. You need everything you can to work for you, not against you, and scrunchy boots make your legs and ankles look bulky. That’s just the way it is. (via slouch boots)

Have trouble fitting your thin calves?

Joan Smalls These boots are too big on her calves in my opinion. (via thestreetmode)

Here’s the solution: Buy knee boots with a side zipper going all the way up, and a cobbler can take them in to fit.

Here are some of my favorite boots this season:

Frye Melissa Button Boot from Nordstrom, $347.95.

Elaine Turner Jayden wedge boot in cognac, $475.

Banana Republic Whitlie boot in tawny brown, $225.

Thick calves? Buy extended calf widths from J. Crew and Stuart Weitzman, among others.

And who shouldn’t wear tall boots? Petite women. You lose any height you have when you cut yourself in half with a boot.

Are you ready to invest in a pair of boots but don’t know what you want or can’t find them at a decent price? Allow us to assist. Our clients receive special discounts at many stores when you shop with us! Email us at and check out our website at

Thanks for reading!




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