Fall Boot Guide

Fall ushers in a whole new category of footwear: boots. A strong boot game includes both dressy and rugged options. The best thing about any pair of boots is that, with few exceptions, they’re versatile enough to enhance any outfit, no matter the situation. Here, I’ve rounded up some of my favorite fall boot styles.

1. Chelsea Boots

Best Fall Boots for Men Brown Leather Chelsea Boot - He Spoke Style

Jack Erwin Chelsea Boots

Chelsea boots are among the most versatile boot options out there. They’re also some of the most comfortable. So much so, in fact, that I like to call them the loafers of the boot world.

The simple construction with an elastic ankle strip makes them easy to slip on (and off). Wear them with jeans, chinos, trousers, or a suit.

2. Cap Toe Lace-Ups

Best Fall Boots for Men Brown Leather Cap Toe Lace Up - He Spoke Style

Tawny Goods Toe Cap Boot

You can never go wrong with a classic pair of cap toe lace-up boots. In fact, if you’re in the market for your first pair of dress boots, I’d highly recommend a pair of cap toes be your first choice. Keep them simple and in a neutral color and you’ll be able to style them with a suit/nice trousers and a blazer or casually with jeans.

3. Rugged Casual Boots

Best Fall Boots for Men Casual Rugged Timberland - He Spoke Style

Timberland Earthkeepers

For a casual weekend kicking it around the city. For a hike in the hills under the colorful fall foliage. For sitting around a campfire on a chilly night. These are a few things for which you’ll want a good pair of casual boots.

4. Suede Ankle Boots

Best Fall Boots for Men Brown Suede Ankle Boot - He Spoke Style

To Boot New York Suede Ankle Boots

Suede is one of those rich, warm and nicely textured fabrics that’s perfect for fall. These aren’t your everyday boots – especially in the rain – but they can add a luxurious touch to even a casual outfit. If you’re looking to impress on a first date, a pair of suede boots will do the trick.

5. Wingtip Leather Dress Boots

Best Fall Boots for Men Dark Brown Leather Wingtip Dress Boot - He Spoke Style

Allen Edmonds Dalton Wingtip Dress Boots

When you’re talking about dress boots, nothing comes close to the style and elegance of a great pair of wingtip leather dress boots. They add what I’d call “rugged class” to denim and pair perfectly with suits in hearty fabrics like tweed.

For those with an eye for signs of wear: yes, my Daltons are in desperate need of some TLC. I’ve been deliberately putting that off so they’re in tip-top bad shape when we do a video on shoe shines and shoe maintenance.

6. Chukkas

Best Fall Boots for Men Brown Leather Chukka Boot Clarks Desert Boot - He Spoke Style

Clarks Beeswax Leather Desert Boot

If the Timberlands are one end of the casual spectrum and the AE Daltons are on the other side as dressier, the chukka boot is somewhere right in the middle. There are various gradations of chukka boot and the nicer the leather, the more you can dress them up.

Get some boot wearing outfit ideas in the Style Guide.

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style

Photography by Rob McIver Photo

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