Boots Men Should NEVER Wear

August 24, 2023
Boots can make you look and feel like a badass, but unfortunately, not all boots are created equal. Some boots will make you look like a dumbass. So, I’m going to go over a few boots that you should never ever wear.

Boots are the most rugged and masculine footwear option for dudes. Slipping them on makes you feel more confident and look like a badass. You look rugged and more masculine. But one of the other things I love about books is that boots will give you an extra two inches of height. That being said, I see men wearing boots they shouldn’t. Thursday Boots are an investment in comfort & confidence. Click to get a great pair of Thursday Boots + free shipping & returns.

  1. Cheap boots. I’m talking about the quality, not the price. Fake leather or plastic boots are not quality and will fall apart after a season. You’ll have to reinvest in a new pair. In the long run, ‘cheap boots’ will be more expensive than boots made of genuine leather. Natural leather will last longer, feel better, and look better. It looks better with time and age than cheap plastic boots that fall apart quickly.
  2. Dramatic boots. You should never wear a boot with a dramatic toe, such as too pointy, bulky, or square. You want the toe to be more natural and rounded. Check out my example of a classic boot that has a cap toe and a little detail. It’s nice and round and not too pointy or square. It’s not too bulky.
  3. Wrong boot combo. You should always wear the correct combination of dressiness with boots. When pairing boots with an outfit, some are ultra-casual, while others are dressier. If not coordinated, you will look silly. Check out the options that go from super casual to more formal. You can take your outfits into a different dimension level when paired correctly.
  4. Boots + stretched over denim. You don’t need to have your pants go over the top of the boots. So if you wear skinny jeans or slim fit, the boots’ top will look weird and awkward with denim stretched over. I love Chelsea boots because you can wear them with skinnier or thinner pants opening due to the lack of laces. Another option is cuffing your jeans to expose your boot. This is totally cool and more stylized, especially with raw denim, due to the detail down by the ankle when cuffed. You want to avoid the pant leg stacked when wearing boots with slacks or dressier pants. You want to ensure the pants’ legs are large enough to lay nice and cleanly over the top of the boots.
  5. Uncoordinated boots and belts. Boot and belt matching can get tricky. Wear a high-shine black belt if you’re wearing high-shine black boots. But casual boots should be paired with a more casual belt such as fabric or canvas. For instance, a brown suede boot can be paired with a fabric or canvas belt. The beautiful thing about suede is its rich texture, so adding another material to the mix while coordinating with your outfit is fantastic. Check out my other examples.
  6. Bulky boots. Boots with a lot of stuffing, padding, or weird soft shapes will make you look shorter. They are also not aesthetic. Go for a lower-profile boot.
  7. Boots that have to be broken in. If you slip on boots that are not comfortable immediately, the boots are not suitable for you. The belief of having to break in shoes and boots is a big misconception. The break-in process often means you’ll have blisters and pain, and you won’t be able to enjoy your boots fully. Thursday Boots has no break-in. You literally slip them on, and they’re comfortable.
  8. Super expensive boots. I used to think you needed to spend $500 to $1,000 on boots to look stylish. You don’t. You’re simply paying for a brand name.
  9. Super trendy boots. You should look for timeless boots in terms of color, construction, and shape. If you do this, your boots will last longer and look better.

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