The Best Knee High Boots

Tina, here.

Skirts (and dresses) and Boots. Do you have to wear hose or tights? Can there be a gap of leg showing between the bottom of your skirt and the top of your boots? Do you match the color of your boots to your skirt? If you are wearing tights, do you match the color of your tights to your boots or to your skirt? Can you wear short booties with a skirt or dress (no - I'll be addressing this in depth, with illustrations, but I wanted to immediately save you from this faux pas during the holidays; stay tuned). These are the riddles I solve, and the questions that probably only bother you when you're trying to get out the door and don't have time to google it or check pinterest. Answers below, with outfit ideas and all the best boots - most are on sale!

The following content may contain affiliate links. When you click and shop the links, I may receive a commission. 

Sweater | Denim Jacket (similar, mine is old) | Skirt (similar, mine is old) | Boots (another option)

(Most of what I wear I've had for years ~ my philosophy is buy what you love and keep wearing it, adding a few fun trends each season to keep it fresh and multiply outfits. As always, scroll down for lots of outfit ideas you can copy or update what you have.)

The Best Christmas Gift To Give or Receive! A Virtual Wardrobe Package With Tina!

from Mini-Sessions to Complete Wardrobe Makeovers

First, hose and tights. No, you don't have to wear them. If it's cold, feel free, but it's not necessary. If you're worried your legs are pale like mine, try lotion or a tanless lotion. Or just don't worry about it (like me). I've got more tips on hose and tights below with the outfits.

Next, the bottom of your skirt or dress does not have to meet or cover the top of your boots. A little glimpse of leg is ok, but not too much. If you're wearing tights, you can match the color of your tights to either your boots or your skirt. The point is, you don't want to break up your legs, so keep a continuous color. That's another reason why you don't want too much leg showing - the boots will hit unflatteringly mid-calf.

What color boots? I always recommend buying a brown pair before black because brown looks so much softer against our legs, and it pairs better with other colors and even neutrals. And, they are easier to wear in early Fall and late Spring with, what else, but white denim (skirts, for example). If you have skinny legs like I do, you'll want a stretch suede so you're not swimming in the boots. If you have a high arch (also like me), a zipper makes it much easier to get in and out of your boots. Can you narrow the shaft of your boots? Yes, but it can be expensive, and the results are never what you think they'll be. Better to wait on the perfect boots and pay for them, than chase good money after bad.

If you have wider calves, more and more shoe designers are giving you that option. It's so nice of them, isn't it? But it means, you have to buy early because they don't make a whole lot, and inventory in general is just low everywhere.

One final point. I'm not into over the knee boots. They're fine and all, but not what I would call a classic, and I just think they look a little weird. Like those toeless boots. What's the point? Anyway, here are the best boots out there right now!

Wearing Tall Knee-High Boots

First, the hose and tights. Remember to match your tights either to the color of your boots, or the color of your skirt or dress. Hose should always be sheer, and close to the color of your skin, or sheer black. Don't ever try to wear a darker color to make your legs look tanner.

Thanks so much for stopping by. Be sure and check out the new Holiday Gift Guide! Be a part of our Insiders Collection for just $5 and discover all my secret sources and favorite finds!

Best,

Tina

New items and ideas for home and wardrobe
Wardrobe and Home Collection
Founder, Tina Adams
Hire a wardrobe consultant