Fall Boot Guide

Best Fall Boots Timberland Earthkeepers

7 / 16
A Casual Classic: Timberland Earthkeepers

Best Fall Boots Donald J Pliner Barton Suede Chelsea Boot

9 / 16
Affordable and quality suede: Donald J Pliner Barton Chelsea Boot

Best Fall Boots Mr Hare Trane Suede Boots

10 / 16
Splurge: Mr Hare Trane Suede Boots

Best Fall Boots Tom Ford Suede Jodhpurs

11 / 16
Really, really splurge: Tom Ford Suede Jodhpurs

Best Fall Boots Allen Edmonds Dalton Wingtip Dress Boot

12 / 16
A modern classic (and my favorite): Allen Edmonds Daltons

Best Fall Boots Johnston & Murphy Conrad Wingtip Dress Boot

13 / 16
More affordable: Johnston & Murphy Conrad

Best Fall Boots Florsheim Jet Leather Chukka

15 / 16
Affordable leather from Florsheim

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


Chime In

  • http://www.thekentuckygent.com The Kentucky Gent

    Got my first pair of Clark’s Chukkas a few weeks back, they’re some of my favorites now.

    Josh | The Kentucky Gent

    • http://www.stylegirlfriend.com Style Girlfriend

      You *just* got Clarks chukka boots, Josh?!?!

      • http://www.thekentuckygent.com The Kentucky Gent

        I know.. I know. I’m the worst. BUT I’m not a big brown footwear kind of guy, and I just found a pair of black ones that I liked.

        • http://hespokestyle.com/ Brian Sacawa

          Wait, you don’t like brown shoes?

          • http://www.thekentuckygent.com The Kentucky Gent

            Haha. I have some brown boots, but otherwise not so much. I wear mostly black shoes.

          • http://hespokestyle.com/ Brian Sacawa

            I’m all about brown. Obviously.

    • http://hespokestyle.com/ Brian Sacawa


  • Sourav Tantubay

    Just in time! Brian, I am planning to purchase a pair of AE Daltons. Can you recommend a color for it? I currently have a black oxford and a AE McAllister in walnut calf. Should I take the AE Daltons in the walnut color? What other color would you recommend?

    • http://www.stylegirlfriend.com Style Girlfriend

      Personally, I love the oxblood or dark chili..they’re a little bit different but will still go with most everything in your closet

      • http://hespokestyle.com/ Brian Sacawa

        Darker is the way to go!

        • Sourav Tantubay

          Thank you for the suggestion! The oxblood Daltons looks amazing! Would that color be more versatile as a boot or as a oxford cap toe?

          • http://hespokestyle.com/ Brian Sacawa

            Oxblood is a very versatile color. If you’re looking to supplement your seasonal wardrobe, I would steer you towards the boots. Fall is the time for boots and, like in the photo you attached, a great pair of boots does wonders for dressing up jeans.

            So if you’re a blazer with jeans kind of guy – I like to call this style “sharp casual” – I’d go for the boots. If you work in an office with a more formal dress code, cap toes might be a better investment.

            I have to tell you, when it comes to purchasing a pair of AEs, it’s a good idea to get with someone who fits for AEs specifically. They have several different lasts and if you’re one size in one particular style, it doesn’t mean that the same size in another style will fit you perfectly.

            For example, I have a narrow foot and wear a 10B in the Strands and Daltons, which are made with the same last, if I’m not mistaken. But my Parkways – also in a 10B – are just slightly longer than I’d like, though I wear them often.

          • Sourav Tantubay

            Well that helped me decide for sure. As you said these shoes are an ‘investment’. I would rather have something that I can use more often. And as I spend more of my time at office, and even socialize in a formal environment :-| , I’ll go in for the Strands in oxblood. (And keep a lookout for the Daltons on a sale). Thanks again!

          • http://hespokestyle.com/ Brian Sacawa

            Great! There really is no bad choice here. It’s all about which kind of footwear fits your lifestyle and profession the best.

            Let us know what you think of the Strands when you get them and be sure to share a photo here!

          • Sourav Tantubay

            Sure Brian! I will!

          • http://hespokestyle.com/ Brian Sacawa

            Cheers, my friend! Thanks for the support.

          • Sourav Tantubay

            My Oxblood Strands are here! They look amazing paired with navy trousers! Walnut/Brown almost feels ‘boring’ now in comparison. Thank you again for the suggestion!

    • http://hespokestyle.com/ Brian Sacawa

      Seeing as how you’ve got a pair in a lighter brown, I’d recommend something darker. Mine are the dark chocolate calf. I like this color because they are a little bit dressier and easier to pair with a suit to keep it dressed up.

  • http://www.flightofspice.com DICAROLINA

    Chelesea boots look great. Love that look x

    • http://hespokestyle.com/ Brian Sacawa


  • Eric Z

    Are those Jack Erwin’s the new one’s from the Foster Collection or from a different year? They look different than what is currently available on the JE website. Thanks!

    • http://hespokestyle.com/ Brian Sacawa

      Good eye, Eric. They’re from last year’s collection, I believe. This year’s style has a rubber sole.

      • Eric Z

        Thanks Brian. I wish I could get my hands on those.

        • http://hespokestyle.com/ Brian Sacawa

          Try sending them an email? Perhaps they have some back stock. Worth a shot!

  • https://www.FrankWilder.com Frank Wilder

    Creating is the best type of thinking – Frank Wilder


    Nice shoes.


  • Zane

    Hey Brian,

    Been meaning to get a pair of suede chelsea’s for quite some time now. I have heard great things about Jack Erwin, however, they unfortunately do not ship to Canada… Do you have any brand recommendations for a chelsea boot in a similar price range?


  • ClossEnough

    Awesome list. ThanQ! In few weeks I am going to Europe and I have heard that it cold there so I have already bought cool combat boots . Great value & look as though they should cost more. + very comfortable.

  • http://classydapper.com Classy Dapper

    I’m digging Chukkas this season so much Brian! Looks and feels great under this sluggish weather in London.

  • trebalack

    Anybody knows what kind of Timberland Earthkeepers shoe on picture 3#?