How to Wear Knee High Boots + Style Tips

It’s boot season!! When the weather gets cold, all I want to do is put on my knee high boots for every single outfit!

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Though I have many different styles of boots in my closet – knee high boots are like really warm socks that you can wear outside and be fashionable at the same time. Maybe that’s why I love them? 

I bought a pair last year that has the tie string in the back, but they slide down my leg fairly consistently…. not a good look. So, when I started looking for a new pair this year, I make sure not to purchase a similar style. I ended up finding this great boot  on Hautelook – the Nordstrom Rack app! They were on sale for $99 (and still are) and the comfiest pair of heels, if there is such a thing.

The most common way to style them is over a pair of skinny jeans and with a chunky sweater. Pick a color of sweater in a style that you feel great in, like I did with this poncho sweater here. You can let the sweater hang depending on the length, but if it goes way too far past your waistline, a french tuck is preferred! Accent the waistline.

One of the tricks I use when wearing knee high boots is wearing your socks OVER your leggings or pants. If you are wearing skinny jeans or leggings, socks will fit over seamlessly. If you have a pair of straight cut or boyfriend jeans, wrap the excess fabric around your ankle and use the sock to hold in place. Boom – now the bottoms  of the pants don’t get bunched up in the boot. The sock allows for a smooth foot in and foot out.

KNEE HIGH BOOT STYLE TIPS on how to choose one for you:

  • Find a Pair That Fits You Well.  // Like I mentioned, I learned from my old boots that I want them to be more snug around the calf are or straight up so I don’t have to keep fussing with it.

  • Pay Attention to the Heel. // For one, make sure you can walk in them. If you don’t like stiletto heels, there are different styles of heels so you are excluded from any of them. Opt for a wider heel, a wedge or a chunky heel to make you more comfortable and stable for strutting down the street.

  • Mind Your Toes.  //  Knee High boots come in different styles of toes as well. The pair I purchased here has a pointed toe but there are options for square, round, or boxier looking shoes. I prefer the pointed or round toe since it elongates the body. 

  • Don’t Spend Outside Your Lane.  // Listen, I want a pair of Stuart Weitzman Boots but they are way out of my financial lane currently. However, I look for styles and brands that have a similar look and feel and google all the places to buy to find a great deal. Feel great about your boot AND feel even better about your investment. I tend to scan Steve Madden, Sam Edelmen, Nine West and others that are modern and affordable. (Or just follow me here and I’ll keep posting great options!)

If I had to head back into the office with this as a work look, I would throw this exact outfit, grab my Lo & Sons backpack and head out the door. It is trendy, in season, casual and still office appropriate too. This black knee high boot is a great staple for any wardrobe that will get use year after year, What do you think of this look?

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Jackie Signature


Author: Jackie

A marketing professional and lover of all things fashion and style, blogging on nights and weekends.

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