Our Picks for the Best Men’s Boots for Fall Under $100

Every man should have a few pairs of quality boots in his closet, especially as the fall weather starts to roll in, but it can be a challenge to know where to look or what brand to pick when you’re on a budget. Below, I’ve pulled together seven pairs of affordable mens boots to help you narrow down your list. Each comes from a trusted brand that I’ve worn or reviewed myself and all of them can be had for under $100 plus Cash Back in your pocket.

Clarks Hinman Mid Boots

While Clarks offers a wide variety of styles for men, it is well-known for its chukka boots. They are as popular as ever and a mandatory pick if you don’t have a pair of your own. This pair from Clarks checks all the boxes for fall style in 2020. Natural tones like tan are in this year, and the suede material makes it a real winner for the new season. Pick them up while you can.

Clarks Hinman Mid

Wolverine Floorhand Boots

Wolverine is a legendary boot company known for manufacturing quality footwear. Its 1,000 mile boot was first introduced in 1914, but it’s far beyond the $100 price range. Not to worry, though. You can still get the Wolverine quality and look at an affordable price. Chunkier work boots are in style, and this jet-black model called the Floorhand just happens to be puncture-resistant and fully waterproof. Form and function make a perfect pair.

Floorhand Puncture Resistant Steel Toe 6" Boot

Vance Co. Cap-Toe Dress Boots

I strongly believe every guy should have a pair of cap toe boots or shoes in his closet, and these are more unique with a bit of a western flair. It comes in four different colors: Black, grey, brown and tan, so you can choose one that will give you the most wear. The heel pull tab makes them extra easy to slip on quickly.

Vance Co. Alex Men's Cap-Toe Dress Boots

New Look Hiker Boot

Moc toe boots are incredibly comfortable and durable, but they’re generally expensive, especially if you’re looking at options like Red Wing’s heritage line. This boot from New Look will give you the same look for much less. They clock in at just under $70, which is a steal if you ask me. ASOS offers free shipping and returns so you have nothing to lose by trying them out.

New Look Hiker Boot


Timberland Groveton Chukka Sneakers

If you’re looking for an everyday, super casual shoe that resembles a pair of men’s boots, look no further than this pair by Timberland. It mirrors one of the brand’s most popular styles without the chunkiness. This is great to throw on with a pair of jeans and cool jacket or you can easily dress it up with a nice blazer. More perks: These are rated five stars and made exclusively for Macy’s.

Timberland Groveton Chukka Sneakers

Eastland Leather Ankle Boots

If you’re searching for mens pull-on boots, like a Chelsea boot, look no further. This model is stylish and built for everyday wear. You could wear these to work with some chinos or dress them down with a pair of cuffed jeans on the weekend. Either way, you have options.

Eastland Leather Ankle Boots

Nunn Bush Odell Wingtips

Wingtips are another men’s style staple, and they look especially nice on a dress boot. Nunn Bush makes high quality shoes at affordable price points and the Odell boot is no different. I’m partial to the black pair, but brown is available as well. These boots could be worn with everything from dress pants to jeans. If you scuff them up over the weekend, they could easily be polished before you head back to work on Monday.

Nunn Bush® Odell Wingtip Dress Boots

Looking for a different style than what I featured here? Search Rakuten for affordable men’s boots and explore the wide variety of options that are available. Remember that when you shop with Rakuten you’ll earn Cash Back on every qualified purchase, so make sure you become a Rakuten member soon!

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