Finding the Right Fit: Men’s Fall Boot Edition

November 7, 2015

So, there’s this common misconception that only women have issues with finding the right size and fit for shoes and clothes. Or that only women care about finding the right size and fit for shoes and clothes. (I know men, how unfair is that? I hear you).

And, I’m sure there are a lot of (mostly outdated) reasons for why these misconceptions (still) exist — why there are plenty of advice articles that revolve around women and addressing (i.e. fixing) their “body type” — and why a Google search for “finding the right boots for men” mostly yields results for men’s cowboy and hiking boots. (Really? This is 2015, right?…)

But, whatever the (misguided) reasons behind these misconceptions and assumptions, I think we can all agree that men — like women — also appreciate finding shoes and clothes that fit well. (Shocking, I know).

Which brings me to my next installment of fall boots — this time, for men.

I convinced my Mister to come try on some boots for the good of the Cause For Bringing Awareness to Men’s Sizing and Fit in Fashion. And, let me tell you, he had a lot to say about sizing and fit.

His main goal was to find boots that were comfortable (with good arch support) and durable, and he wanted to be able to take his shoes on and off quickly — something that is often compromised with boots. He was also a little bit skeptical about boots being “his style,” but was willing to try some on. We went to Nordstrom and Macy’s, and he tried on a total of seven boots from six different brands, in similar styles. The Mister’s shoe size is usually a US Men’s 9.5.

Here’s what he found:




Rockport Toloni Boots ($135) — The two reviews currently on Macy’s website have slightly different verdicts about size — one says they run half a size small, the other says they fit true to size. According to The Mister, these shoes were loose around the arch of the foot and too roomy around the ankle, making it altogether awkward when walking. The heel was also hard and rather uncomfortable with lots of additional spacing in the very front (though not enough to warrant going down a half size). All in all, not the right fit.






Bar III Devin Cap-Toe Boots ($85) — I thought these shoes were awesome. They said “Let’s grab a cup of coffee after my lecture and talk about Shakespeare.” Boots talk to me that way. But for all their charm, The Mister was not convinced. They cut into the top of the ankle with meager comfort in the sole of the shoe and no padding. Compared with the first boot, though, it was a better fit in the front and the ball of the foot. So, some improvements, but they didn’t quite pass The Mister’s test.




Johnston & Murphy Copeland Chukka ($150) — These shoes walk that dressy-casual line really nicely, but walking that line doesn’t feel so great when you have a couple of spots that pinch a bit, which was the case for The Mister. He did report that the heel and sole of the shoe were much, more more comfortable than the previous shoes and that the friction he initially felt at his ankle lessened with walking — maybe they just need some breaking in? Ever the practical man, he noted that there was no super convenient zipper, but qualified this knock by admitting that the laces were less involved than others. Some progress, but not quite a ringing endorsement.




Wolverine ‘Montague’ Chelsea Boot ($294) — I thought these boots said “Oh, I was just outside cutting some firewood for you so we can relax by the fire and drink an old fashioned.”  Which is perfect in my book. The first thing that The Mister noted was some pressure on the top of the foot. Plus, it was wide around the ankle — though not as wide and unstable as the first Rockport Tohoni boots. The sole felt “fine” but not as comfortable as the previous Johnston & Murphy Copeland boots. I did, however, catch The Mister eyeing this pair like maybe he’d found a winner.





Johnston & Murphy 1850 ‘Karnes’ Brogue Cap Toe Boot ($198) — I thought these shoes were pretty snazzy. Kind of dressy, kind of edgy…very stylish. The sole of the shoe (a point of importance for The Mister) was in the middle of the comfort spectrum. So far, the Copeland J&M’s were the most comfortable, followed by the Wolverines, then this pair, Bar III, and lastly the Rockports. The padding on the back of the shoe, where the top hits the achilles, was much appreciated, and there weren’t any notable pinch points, which was good. Maybe the stylishness of this one trumps the middle-of-the-line comfort? Maybe? No? Okay…Next…





To Boot New York ‘Stallworth’ Cap Toe Boot ($450) — Look at that gradation in color! Such a thing of beauty! I mean, I want to wear these boots. But let’s focus on The Mister. He was unimpressed. He had to go significantly down in sizing to an 8 because these shoes run very large. He reported that it was snug around the edge of the big toe, loose around the ankle, and tight just above the ankle, making it all confusingly simultaneously loose and tight. And, in general, he felt like his foot was “wrapped” which did not feel so great. So, that was a pass on this beautiful, beautiful boot.





Timberland ‘Wodehouse Lost History’ Boot ($299) — I thought these shoes were charming. They said: “Sure, I’m game for walking through the forest with you on a crisp fall afternoon.”  Just what I wanted to hear. Turns out, these boots are slightly bowed, which make them perfect for strolls outside. The Mister wasn’t quite sure about the bowed feeling, having never tried it out before. He is on the fence about it, but the leather is soft which will make them easy to break in and there was no awkward pinching.

So there you have it. Proof that men can have (very detailed!) opinions about fit and size, too!

(And clearly we’ve all learned that every man should own a pair of boots, amiright?)

At the end of the day, the Mister’s top two choices were the Wolverines for their sleek and understated style and the Johnston and Murphy Chukkas for their comfort.

What’s your experience finding the right men’s fall boot?

(Cover Photo via Bernard Walker)

(Other photographs via Anna Medina)


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  • Reply Herbert Yang November 14, 2015 at 11:16 am

    To find out more about Mister’s personal experience with these boots, take a look at his posts on as user “ramedina”

  • Reply Herbert Yang November 14, 2015 at 11:20 am

    To find out more about Mister’s personal experience with these boots, take a look at his posts on Linkqlo iOS app as user “ramedina

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