How to PROPERLY Wear Boots! | Top 5 Boot Wearing Dos & Don’ts

September 8, 2022
Today’s video is all about my favorite footwear. Badass boots! More specifically, I will review my top boot-wearing do’s and don’ts to ensure that you always look your best whenever you wear your most badass footwear. I’m breaking this down into two parts: the first part goes over the do’s and don’ts, and the second part shows you outfits and my favorite ways to rock badass boots.

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How to wear casual and dressy boots

  1. There are dressy, casual, and work boots. When dressing boots up or down, make sure the boot you’re wearing is suitable for the outfit. Work boots are a unique situation we’re not going to address.
  2. Know your different types of boots, which I will take a quick rundown of. The Chelsea boot is a casual or dressy slip-on. Lace-up boots are more casual and come in refined options. It’s a clean, simple, and sexy boot That is incredibly rugged. The lace-up can also be a bit dressier with a brogued wingtip. A chukka boot is another lace-up option that looks more like a desert boot and is less rigid inform and structure.
  3. Choose the correct boot for your particular pair of jeans. If the jeans you wear are more casual, which can be a little lighter or distressed, choose a more casual boot. If you’re wearing a darker washed and non-distressed in them, super casual boots look stupid. You’ll want to go with something a little more refined and polished.
  4. Know how to style where your boots and jeans meet. Never tuck your jeans into your boots. Also, stack your denim (don’t try to pull your jean super tight over the top of your boots). If you want to cuff your denim, this step adds detail to your jeans and exposes your boots.
  5. Every dude should have some boots in his wardrobe, and one pair might not be enough because boots are incredible. They make you look a bit tougher and more badass. Also, boots make me a bit taller as a short dude. They’ll give you an extra inch to an inch and a half to your height.

Check out how I style my boots

  • Slim-fit cargo pants, President boots, a white tee-shirt, denim jacket.
  • Gray over shirt, white tee-shirt, black slim fit jeans, Captain boots.
  • Suede bomber jacket, white tee-shirt, black jeans, Captain boots.
  • Black Henley, green bomber, denim jeans, black Chelsea boots.
  • Gray light white sweater, lightweight blue pants, wingtip brogue boots.
  • Gray suit with chalk stripe (with or without the jacket), black polo, suit pants, dressy boots.
  • Leather jacket from Thursday Boots, white tee-shirt, distressed slim fit gray jeans, Cavalier boots.

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