February 25, 2019

Boots & Booties: What To Wear With What

Sydne Style shows how to wear boots and booties with fashion tips

I love when you request post topics. A) It makes my job easier and B) this blog is all about you! So it feels great to be able to provide exactly what you want. One question I got asked last week is about boots and booties, both what to wear them with and how to transition them from winter into spring. So let’s get started and talk all things boots and booties!

over the knee boots

I’m obsessed with over the knee boots for winter. I actually did a whole YouTube video about how to wear over the knee boots. Here are my three top tips for wearing them:

  1. Match your boots with your pants. This creates a long and lean silhouette and gives the illusion of height!
  2. When wearing them with a mini dress or short skirt make sure you have a higher neckline. It’s all about balance when it comes to showing skin. I also love them layered under a longer skirt or dress. They’re warmer than just a a pair of tights!
  3. Stick to leather or suede. I know patent is very in right but unless you’re a model showing off her street style, a patent thigh high boot can give off Pretty Woman vibes (before the hooker transformation).

As for transitioning them into Spring? I prefer over the knee boots for colder seasons. So when it eventually does warm up, I store mine until Fall.

knee high boots

Knee high boots are great for transitioning seasons. I especially love tan or nude boots for this. I have a pair of tan heeled boots that I often wear with knee length skirts and dresses. Then I wear my snakeskin ones with jeans.

I also love flat knee high boots. I have a black pair that I usually wear with jeans when I’m traveling. My big tip for knee high boots is buy half a size up. This allows you to wear a thicker sock when it’s cold. Plus, it’s helpful when traveling in case your feet expand.


Booties work year-round! Depending how you style them, you can wear them every single season. So let’s break it down by when it’s cold (now!) to when it’s warmer (c’mon Spring!).

Booties for cold weather…

The big question I get asked about wearing booties with pants is whether to tuck in or tuck out. Well, this depends on the boot and the pant. When I’m wearing a straight leg or flare jean, I usually layer my booties under my pants. This works best with taller booties and sock booties. If I’m wearing a skinny pant, like leather leggings, I’ll tuck my pants into my booties. It helps if you tuck your pants into ankle socks first to keep them secure.

When wearing booties with tights, follow the same rule as we chatted about for over the knee boots and match your booties to your tights to look taller.

Booties for warm weather…

For warmer months, it’s all about where the bootie hits at your ankle. My rule of thumb is never to have the bootie hit exactly at your ankle because it can make your legs look stumpy. I either go with boots that hit above my ankle or booties that dip below my ankle.

When wearing booties with jeans in warmer months, I like to go with cropped jeans because showing your ankle can make you look slimmer. And when wearing booties with dresses or skirt, I generally go for nude booties to lengthen my legs.

I hope these tips helped you! Feel free to ask any more questions below and keep those post suggestions coming. I love hearing from you!

Leave a Comment


  1. Linda Evans commented:

    I really impressed by your overview. Very good job! I loved the advice to pick knee boots with a higher neckline. It’s true, that there ought to be a balance in showing the skin. Thank you very much for this helpful post.

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    • Sydne commented:

      So glad you liked the post Linda!

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  2. Michał commented:

    You are an exceptional lady in long leather boots!

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    • Michał commented:

      … and booties!

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