Top 5 Dress Boots for Men

January 3rd, 2014

As you might already know, I’m a former sneakerhead turned footwear collector. While I’ll always have love for a fresh pair of original Js, I have a stronger jones for a well-made pair of leather bottoms (which can be a much more expensive habit, at least in the short term).

Of all the types of footwear I own, I would have to say that dress boots are my favorite category. They’re equal parts dressy and rugged, making them a versatile choice to enhance just about any look, under just about any conditions.

Here I put together a quick recap of my five favorite styles of dress boots, along with some recommendations for good affordable options available now. If you’ve been thinking about a new footwear investment, any one of these styles will be among the most versatile pairs in your rotation, and since so few guys have good dress boots, you are sure to get plenty of compliments on them.

1. Sharp Chelsea Boots

The chelsea is sort of like the loafer of boots. It’s an easy slip-on style with an elastic ankle for flexibility and comfort. My advice is to look for a pair that has a sharp chiseled toebox similar to that of a benchmade pair of oxfords. Avoid anything overly round, chunky or “outdoorsy”. Instead, keep them sharp and lean, and wear them with everything from slim suits to stacked denim.





2. Sleek Leather Chukka Boots

Desert Boots with crepe soles (like Clarks) are very popular, but they will always look unmistakably casual. I prefer something a little sturdier and luxurious looking with leather (or thin rubber) soles. Again, avoid clunky toes, bulky soles, anything with unnecessary stitching lines, contrast laces/soles, buckles, straps, logos, etc. Keep ’em clean & mean for greatest versatility.





3. Captoe Lace-Up Boot

It’s hard to fail with a classic captoe lace-up boot, especially in a deep oxblood. As with all versatile footwear, keep them neutral, simple and streamlined and you’ll be wearing them over and over again, no matter the occasion or weather.







4. Jodhpur Ankle Boot

The Jodhpur is a sexy boot. The ankle strap gives it some attitude, but its simplicity makes it very easy to wear. These are perfect for a night out on the town but work just as well for a day at the office.





5. Wingtip Brogue

We’ve proven the staying power of the wingtip brogue time and time again. This is a boot that works just as well with suit trousers as it does with jeans, and they’ll only get better with age.






So what’s your go-to boot style? Use the comments below to share!

Thanks, as always, for reading. 

Yours in style,

Dan Trepanier

Shop Custom Menswear Made in America


Take me to the Shop

  • packer fan 156644

    Going in casual attire to a Packer game dressed from this affordable company gives me an added treat of being comfortable from the flight to and flight home. Outstanding choices and these products really look smashing. A+

  • Jay

    Would love to know who makes those Suede Jodhpur boots?
    anyone have tips on affordable Jodhpurs …I mean as perfect as YSL looks…I was hoping for some good knock offs in larger sizes?

  • Paul

    Dan, I am interested in your thoughts on a cap toe, lace up boot in tan grain (kinda like walnut). Since it’s a lighter color, what outfits can I wear with it in the winter? (besides denim). I have a lot of winter wools in grays, navy’s, even dark browns. Would that work? I work in a university setting, not the corporate office, so it’s more ivy style, lots of layering with knitwear and such.

  • Franz

    What’s with the high water pants? Lame!

  • Vancity

    Hey there, what brand of Chelsea boots are you wearing in the pics? Also, I can’t find the ones you mentioned.. What others do you recommend?


  • Rob

    This is about 9 months late, but who makes the Chelsea boots shown in the first set of pictures?

  • sam

    How about a list of boots your model is wearing? brand, style?

  • http://undefined Dick Lickerson

    I really like boot #2; the little flap reminds me of when my uncle made me look up his kilt as a young boy.

  • http://undefined Big Jon

    What, no Tims? You gotta have Tims on the list.

    By the way, please forgive me if this is a stupid question, but is it “chuck-a” or “choo-ka”?

  • Jeremy Whitechick

    Yep. This post is hard evidence that Dan Tre absolutely knows what he’s doing. #golfclap

  • Joe

    Speaking of boots and trends that I hope to see die: tucking pants into boots.

  • Cosmetiques homme

    Great blog ! Great articles ! Cheers from France !

  • Miguel G

    For some other affordable boot options, Massimo Dutti is still having a considerable sale.

  • Josh

    I have to say, I really appreciate the inclusion of links to affordable pieces in the same style as those featured in the photos. I love the site, but I often think when looking at the different outfits you post that every single piece you’re wearing is out of my price range. Having links to where to buy affordable versions makes the post a lot more practically useful for me. I’d love to see more of this in the future on TSBMen!

    • Dan Trepanier

      Agreed. I know that I have high-end tastes (and a lot of “connections”) but our message is always “you don’t need money to have style” and “it’s not what you wear, but how you wear it”. One of many chances this year on TSB will be more links to affordable options that I consider to buy good values for the dollar.

      Cheers Josh.

      • Matt

        Im losing my mind trying to find boot #2 with the kiltie like in the picture. PLEASE point me in the direction of where i can find them…

  • Kyle

    No love for those chocolate suede J&M Captoes that you’ve been rocking so hard lately?

    • Dan Trepanier

      They’re suggested in the captoe section.

  • John

    Might I suggest Engineer boots? Chippewa’s non-steel toe version looks classic and is also very affordable. I wear them with blazer and gray trousers combo on a daily basis.

  • Tyler

    I must vouche that the Hutchins cap boots are quite a nice pickup, received mine last week and couldn’t be more impressed.

    Which cap toes are you sporting in that picture though?

    • Dan Trepanier

      Agreed. Love them in suede.

      Those are custom jobs from Scarpe di Bianco.

  • Drew

    Finally a vintage beast post from TSBmen. This is the bread and butter of TSB, informative posts on menswear staples. Great post, it is posts like these that remind me why I’ve been a tsbmen fan for 3 years.

    • Dan Trepanier


  • Calvin

    “I have a stronger JONES for a well-made pair of leather bottoms”

    Is that another one of those words that those GQ kids use like “swag”, “dope”, and “steez”?

    • TO

      Simply, no.

    • Dan Trepanier

      Absolutely not. That’s an old school reference to heroin addiction. And it hits closer to home than you might think…

      Fun fact: the term “Jonesin” (similar to “fiending”) was originally a reference to Great Jones Alley (where the Michael Andrews Studio is now located) because that was the place to score heroin in NYC in the 80s.

      Get your research up before you start calling people out.

      • Just a guy

        Lighten up…good grief, the term has evolved to simply mean craving or desiring…have a coke and a smile…sheesh

    • Calvin

      Aye man chill on that. You’re giving us Calvin’s a bad name.

  • cam
  • only says inspiring


  • Ali Naaseh

    Seems like you’re recommending J&M quite a bit, I just want to add my two cents:

    Just bought a pair of J&M Tyndall wingtip boots (similar to the AE Daltons) and they’re killer. Super comfortable and look better the more they get beat up

    • Dan Trepanier

      Thanks Ali! I think we can all appreciate the style at their price point.

  • http://undefined Jeanscuffed

    Wait, when did you do a Corduroy suit post??! How did I miss this?

  • Boothy

    I was out in the boot market recently and found it hard to find a Chelsea boot with just the right combination of detailing, colour (Black), rubber soles and comfort.

    In the end I plumped for the Steptronic ‘Bassett’ which has a wingtip toe – unusual for Chelsea boots – and after pounding the streets wandering round Paris in the rain, I found them to be the perfect shoe! Im now looking for some Tan brogues and again I really would prefer them to have a rubber sole, because I need some grip. If anyone knows of any nice examples in the 100 – 250 Euro range, let me know!

    • Owen

      For that sort of money you should have a look at Loake. They do various tan oxford and derby brogues with a choice of welted leather or rubber soles.

      I’ve got the Chester 2 in tan and they always get the right sort of attention. They do the otturburn which I think has the same upper, but with a rubber sole.

      Careful though, the sizing is pretty large on these. I would go one full size down. I’m normally 43 but wear a 42 in Loake.

      • Bobbybooth

        Cheers Owen. I did see these on my travels and they hit the mark perfectly. I think your recommendation makes them the winner.

  • Tom H

    Dalton’s are the bomb!

  • Brady P

    Just got some AE Daltons for Xmas/birthday and Ive been wearing them non-stop. People don’t even notice that they are boots, they just look like a sharp wingtip until you sit down or pull up your pant leg to show them off. Be prepared for compliments in these bad boys.

  • BougieHippie

    great look and brilliant shoe choices, my favorite shoe is the ankle boots! they are obvious dress up choice but goes really goo with a crop denim and oversize sweater and wide brim hat.

  • ajb240

    A very timely post as I was just shopping online for black dress boots. Thanks for the info. For me though, dress boots need to be more rugged. We just got hit with a blast of snow here in Pittsburgh and my brown Florsheim dress boots are getting a lot of work because the sole provides needed traction walking through snow and ice. I like the J&M captoe lace-ups but I’d go skidding around town in them. Any thoughts on boots with better traction?

  • Juan

    Somehow, even though without any original content, this manages to be an exceptional post!

    I had totally forgotten about those sexy brown suede Jodphurs! Are those Ralph Laurens? If so, it’s worth noting they’re currently on sale at RL’s website for a mere $149.99!

    As always, great stuff, I’m very much looking forward to what 2014 brings to the table for you guys! I’m sure it’s going to be a terrific year!

    • Adam

      Oh man, those RL Jodphurs look great…I saw them on Dappered a few weeks back. I don’t normally love Jodphurs in general, but something about that pair is just right.

  • Miguel

    I like all of them but can you really wear a suit with the wingtip brogues, I find it hard since they are a little aggressive for a suit, your thoughts Dan.

    • Dan Trepanier

      Could be, depends on your office. I’ve worn the Dalton’s with suits, but I’m rarely in very strict corporate environments. The captoe might be a more conservative choice.

  • AJ

    I bought the J+M Tyndall cap-toe two weeks ago (on sale for 130$).

    While they are slightly long (I’m a size 11, they look like 13 despite fitting well), I absolutely love them. I’ve already had the chance to wear them with a suit, denim, and slacks, receiving lots of compliments!

    • Dan Trepanier

      Nice! Thanks for the affirmation AJ.

  • http://undefined Robert

    In your selection of boots, do you have preference in terms of soles, rubber vs. leather? Being northeasterner, I find when it is boot season, I like the bottom being rubber, since typically there are elements on the ground that have tendency to make leather soles not the best choice. Your take?

    • Dan Trepanier

      Agree. Sleek rubber soles are your best bet. You can also have your local shoe repair man put a protective/grippy layer of rubber on top of your leather soles.

  • Tom

    Aren’t leather soled boots a bit impractical? Rubber soles might not be as dressy but can just as easily be re-soled (if you get a good pair)…

    • Dan Trepanier

      Depends where you live. If you’re trudging through rain, snow and ice, rubber will provide more grip and durability.