Stop Wearing Boots WRONG! How to PROPERLY Match Boots With Jeans, Chinos, Pants, Slacks

January 17, 2024
The other night, I went out to dinner and saw this man walk in. He looked great — super stylish, with amazing hair, and an incredible outfit. He was on point until I saw his shoes. He destroyed his outfit! He was so close! His boots were super cool, but they were more appropriate for jeans. So I want to cover how to properly dress up boots, whether or not you’re wearing jeans or next level such as chinos, slacks or even a suit.

Boots are the sexiest most rugged and unbelievably manly shoes that a guy can wear. The trick is knowing how to combine wearing boots properly because you can take a potential boot opportunity and turn it into a liability by wearing the wrong ones. All the boots that I wear are from Thursday Boots. Thursday Boots are an investment in comfort & confidence. Get yourself a great pair of boots with free shipping & returns today!

Boots bearing rules

Don’t wear cheap boots. If it’s a moral thing, like you’re vegan, that’s fine. But if you want to pinch a penny, don’t do it. Cheap book boots look cheap and fall apart quickly. Spend just a little bit more money and get real leather. They will look amazing!

Do not wear dressy boots with casual jeans. Some boots are casual but some are a little more elevated and aesthetic. Casual boots go with casual jeans. Never wear dressy boots with casual jeans. When wearing dressy boots, some are created to be more casual than others.

Choose brown when dressing up a pair of boots. Brown is more fashion-forward. Guys are comfortable with black because it matches everything. Brown can too, and it adds another level of richness and texture to an outfit. Check out my examples. You can get multiple boots so you can have both colors.

Change the aesthetic of your outfit by switching your boots. Go from something dark and mysterious to more surprising and daring by switching from a black boot to a gray suede boot.

You can dress down a dressy boots but you can’t dress up a casual boot. Dressy boots vs casual boots:

  • Suede is casual; same with matte leather.
  • Stitches around the toe are casual.
  • Shinier is dressier.
  • Rubber soles and ones that stick out further than the upper or the leather are casual.
  • Laces are more casual as well.
  • Dressy is cleaner.
  • Brogues laced up can be versatile.
  • The toe is another indicator: tapered is dressier.
  • The clean, low profile is dressier.

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