How To Style Boots | EP 115

If you’ve been following this podcast at all, you will know by now that Holly loves to talk about boots. All sorts of boots – all styles, all heel heights, all brands. 

Holly Loves Boots…and you should too.

She has reported seeing them everywhere at NY Fashion Week in the Fall of 2022, she owns a bunch herself and she almost never gets through a styling conversation without mentioning them at least 10 times.


What we have not yet discussed is “How to Style Boots,” which is different from “designers are showing boots right now,” and “everyone is wearing boots this season.” #FACTS


If you are a woman of a certain age, and you think you want to wear boots that go up to the top of your knees or even to the middle of your thighs, you need to try them on first. 

If you have crepey skin that falls over your boot tops, these are not the boots for you.  (You know what we are talking about, don’t act like you don’t!)

Get EPISODE 115 here!

There is absolutely no reason you cannot wear any style of boot you love. Cowboy boots, vintage boots, the new lug-sole boot. Boots are timeless (if not practical and just fab).

What matters is HOW you wear them.

(Pro Tip: As always, Holly has curated an episode-specific Pinterest board with all the style suggestions mentioned in this episode. It is always fun to follow along while you listen!)

So, let’s start with the differences. Boots are usually determined by the height of the shaft, or the amount of leather or material that covers the lower part of your leg.

  • Booties:  The shortest shaft, stops at your ankle. Make sure the ankle opening is comfortable, and not rubbing your tender ankle bone skin off. Booties are a great way to get a boot look under jeans without a large shaft that’s going to look bulky. Booties are dressy if they have a high or stiletto heel, and can be sexy.

  • Mid-Height: The shaft stops in the middle or top of your calf.  This is typically a cowboy boot and is a style that will never die. Wear them with shorts, pants, skirts, maxi dresses, or jeans. They are not, however, considered dressy. This is a great way to bring something dressy down a notch to make it more casual. This is a very important fashion fact. #takenotes

  • Below the Knee:  This is the most common, comfortable, and popular style of boot. They look great on people of any height, and can be worn with dresses, skirts, slacks, jeans, and even shorts and tights in the winter! You can wear them season after season. They might go in and out depending on a hot trend, but they really don’t go out of style. These are keepers.

  • Thigh-High: These go over the knee or up onto your thigh. These have the highest shaft. If you are 7 feet tall, you will love these boots and can wear them with short skirts, short shorts or over jeans – anything to show off your 6-foot legs!! If you are not 7 feet tall, well then, wear them under a dress that hits you at the knee to show a little boot when you sit. This is an excellent idea.

From there, you will find any heel height in combination with any shaft height. And, as with all shoes, a higher-heeled boot tends to be dressier, with mid-to-low heels being more versatile. 

So how do you choose? Well, with some major caveats.

  • In the exact words of Holly, if you are going to wear a tall boot, especially ones up to your thighs, make sure it is super cold outside. If you’re a hot-natured person who is schvitzing all the time, an over-the-knee boot is not a good idea for you.
  • Another thing to think about if you are purchasing a new boot style is: Do you have the personal style to support this? If you are super conservative, or if this is a risky purchase for you, make sure you have something that you can actually wear with them – instead of just blindly purchasing something.
    • This is called a style plan, people. If you want an over-the-knee boot, you need to have the outfit to support this. 
  • Cowboy boots: If you want a cowboy-style boot that’s not real cowboy boot, but has the look of a cowboy boot, there are millions of good options. You can shop on Freebird to see different price points and quality, or you can go with a more authentic company like Luchesse, Tecovas, Ariat or Dingo to get the real deal.
    • Fashion Facts: If you buy cowboy boots, you might want to go up a half- or full size because you’re probably going to need a thicker sock. Also, if you’re going to buy new boots, try to find a store to try them on first. You must see what the most comfortable and wearable fit is for you. 
  • Ankle Boots/Booties: These are not necessarily a cowboy style. They can be plain or fancy, and are definitely worn for fashion.
    • Fashion Fact: Low boots that are made for snow or rain are not booties, and you only wear them for inclement weather. Holly is watching. Don’t do it.
Fashion Crime Alert!

Do not wear Hunter rubber boots up to your knees if it is not pouring rain or a hurricane. And do not wear Ugg (we call them Uggggggly) boots if it is not 20 degrees outside. Period. You can walk the dog in them, fine. But these must be worn in. the. cold.

Holly does not care what the weather was when you left your house. If it stops raining or it warms up, you better have a change of shoes in your trunk! 

And finally, the Care and Maintenance of Boots.

If you’re already taking great care of your shoes, most boot companies want you to use a leather conditioner or a non-silicone, waterproof stain protector. 

For someone who’s new to the boot trend, the care of leather is a learned art. Instead, get to know your local cobbler or find a shoe person.  Have your boots waterproofed, regularly cleaned, re-soled if needed, and fix those stiletto heels you keep ruining by stepping into the middle of cracks. Try not to do that, please. 

In summary, anyone can pull off the boot trend! Just don’t go too far out of your reality zone, try boots on before you buy them – and learn to take care of them so you can enjoy this timeless fashion trend forever. 


“The Best Fashion Friend You Never Knew You Needed!”

Hosted by your favorite personal stylist, Holly Katz.

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