Tina, here.

It's boot season! I could wear boots almost every day. They are comfortable, supportive and mostly chic. That is, if you buy the right boots. I see so many awful examples of ways not to wear boots that I found it necessary to show you how to wear them the right way. And what to look for when buying your tall boots. Most of the boot "fashion don'ts" I see involve adults trying to look like twenty-year-olds (over the knee boots + short skirts, boots + leggings, gladiator boots + anything at all). And you do know that trying to dress younger than you are is the fastest way to age yourself, right? Because I love you and want you to embrace your gorgeous, classy, age-appropriate self, here is how to wear tall boots without looking like a sorority girl.

How To Wear Tall Boots

Numero uno rule: your boots, as with all your shoes, must be both comfortable and chic.

It's probably time to update your boots if you haven't in several years, or if you've never been happy with the ones you have. Shop all my best finds, including 7 new styles of boots, inside the all-new Style Vault,

 November 2015: A Toast To The Stylish Life.

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How To Wear Tall Boots

1. Buy boots with very little hardware, harnesses, and buckles.

No reason to shackle your ankles and legs with weights.

How To Wear Tall Boots

The cleaner, the better. I know boots with gadgets and doo-dads are everywhere, but steer clear. The bigger the stuff on your boots, the bigger your legs appear.


That little space of skin between the bottom of my dress and the tops of my boots gives a little breathing room, and keeps the look from being bottom-heavy. With tall boots you don’t need to wear tights unless it’s cold and you just want to. I had tips added to the toes of these boots since they are pointy; that keeps the toe from getting scuffed. Your cobbler can do that for all your pointy-toe shoes and boots. I found 2 beautiful pairs of camel tall boots and just added them to the November Style Vault, Style Notes.

How To Wear Tall Boots

I love one-color dressing. It's chic and easy.

2. If you're only going to buy one pair of tall boots, buy brown boots.

Anything you'd wear with black boots, you can wear with brown boots, and brown boots are much softer paired with all the colors in your wardrobe.

How To Wear Tall Boots

Here's how I extend my denim skirt into cool fall days, with tights and boots. Remember, you don't have to wear tights unless you're cold. Bare legs under boots are just fine.


Dress or skirt just barely too short? Add tights in the same color to create one long line. These boots are Prada, from years and years ago. I added several great pairs of dark brown boots to the November Style Vault, Style Notes. The riding boot is on sale for under $100!

3. Cowboy boots are great paired with the season's midi skirts.

Midi skirts can come off looking frumpy or bulky, or both. If you want to wear one, I like a cowboy boot because it says I'm not wearing my long Carroll Reed skirt circa 1984, but I'm also not trying to be all boho hippie either. I also don't like full, A-line midi skirts; I like them when they taper down to right under your knees so you don't get that bottom-heavy bulk.

How To Wear Tall Boots

Let me break it down for you in a real technical way: the reason this works is that the skirt narrows slightly to my knees, just where the top of my boots hit, which means there's not a wide gap of empty space around my knees. That would make my bottom half look like the bottom of a big, wide triangle. Great cowboy boots, not too western-y, just added to the November Style Vault, Style Notes.


Bonus points for a bias-cut midi skirt.

4. If you wear tall boots over skinny jeans, make sure you don't have elephant knees.


When wearing tall boots over pants, try wearing actual pants, and not leggings (unless you're a sorority girl, and even then, I'm not a fan). Skinny jeans or pants with some stretch in them made from a substantial fabric is what will keep your skinny jeans or pants tucked safely inside your boots.











I think we're clear here.

5. The shaft of the boot should fit your calf.

No stuffed sausages and no swimming bird legs! Athletic calves? Look for "extended calf boots"  or "wide calf"(several new ones added to the November Style Vault, Style Notes) or boots with a stretchy gusset. Thin legs? Look for boots with a side zipper going all the way down, and a cobbler can take them in to fit your calves.

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An old trick to stretch leather boots or shoes: put alcohol on a cotton ball, then dampen the inside of the boots or shoes where you want them stretched, and wear with socks until dry. This will take maybe 30 minutes.

6. To keep a long, lean and uninterrupted line, match the color of your tights to your boots.

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Brown boots with brown tights; black boots with black tights. And the tights need to be opaque. Not hose, but tights, and opaque tights. (Brown stretch suede boots like these, above right, are in the November Style Vault, Style Notes.)

Boots I don't like? Scrunchy boots. Approach with caution. You need everything working for you, not against you, and scrunchy boots make your legs and ankles look big and bulky. That’s just the way it is.

Not sure about your boots? We can evaluate them when we clean out your closet, then we can shop with you and style all your pieces this fall. If you’re in the Nashville area, check out our amazing Nashville Wardrobe Consulting services, and don’t forget to join the Style Vault today to start shopping and saving on brand new items. Seven new styles of boots just added to the November Style Notes!

The Style Vault…Your Subscription To Style

Thanks for reading and all the best,


I’m addicted to the vault!  I can’t get dressed without you!

~ another happy Style Vault insider

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Photos by Krissy Leigh Creative