Beckett Simonon Gallagher Boot Review: an Imperfect But Welcoming Entry Point into Quality Boots

David Garcia is a Stitchdown contributor specifically focused on the sub-$300 shoe and boot market (even though he owns a pair of Alden Indys. So he’s like, legit.)

As we first plunge into that most fulfilling hobby that is quality footwear, we don’t always know where to start—but entry-level brands like Beckett Simonon make breaking in just a little easier. Beckett Simonon’s Gallagher boot was the first major boot purchase I made and because of it, I have discovered a wonderful community of people that share my passion. The Gallagher, although imperfect, presents a perfect stepping stone into that world.

My journey started with a trip to the dreadful store known to the masses as “Macy’s” last year (don’t ever work there). I was in search of the perfect boot, something rugged, but not chonky. There are definitely some “I guess these are good-looking” boots at Macy’s, but my issue was the price tag: they were not cheap, but certianly felt like they were.

As I wandered across the mall with half a mind to get a Cinnabon, I couldn’t help but keep thinking about them. “Why are they that much? They just don’t seem like they should be.” I started looking up terms like “high-quality leather boots” on Google, and of course, it being Google, I got some ads.

“What’s this Beckett Simonon?” I said to myself. “It looks and sounds the part, let’s see.” I was intrigued by their made-to-order approach and use of nice materials and stitched construction; this sounded at somewhat legit. I was all in for the wait, a wait that was worth the while.

Onto The Boots…

The Gallagher, to me, is a straight up looker. With a hybrid silhouette of an Alden Indy boot (see review here) and Crockett & Jones Galway, it’s got a unique flair that many entry level brands miss. I mean, Beckett Simonon does sell more conventional models, but I think the Gallagher gets it. It’s got a great shape and general look to it. When I talk about shape, I’m talking about the last, the mold that shoemakers wrap the leather upper around in order to construct the shoe. The upper pattern features an apron toe that gives the boot a dressy feel (as opposed to its rural cousin, the moc toe—just compare these Gallaghers to a Red Wing 875).

These uppers look and smell (come on, we’ve all done it) great. I opted for their Oak, as the color has such a dynamic look to it, especially when it picks up patina as mine have. The leather itself is a full-grain vegetable tanned calfskin from Argentina, veg-tan being a process of tanning leather by using natural tannins like plant matter and tree bark. It generally takes longer to produce but it results in a tougher, patina monster leather. In the case of this boot, they’re fairly stiff, but never truly uncomfortable, especially after a wear or two (and if you want to learn more about veg-tanning, this is the story for you).

Despite having a substantial look to them, they’re fairly lightweight, with the Blake stitch construction is primarily to congratulate for this lightweight feel. Blake construction usually makes for a lighter, flexible and frankly more affordable shoe by stitching the outsole to insole directly, and all those aspects work together nicely here.

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The Comfort Question

Getting into quality leather footwear comes with a serious change from padded, foamy-boi sneakers or Vans/Converse. Over time in this hobby, I’ve found comfort derives from long-term support rather than initial softness and cushion; the former is exactly what I encountered with these boots.

While going from an Ortholite insole to this leather-lined fiberboard insole was a bit of a learning curve, it also made for something I’ve never experienced before: I don’t want to take off my boots at the end of the day. It maybe has to do with the soft vachetta leather Beckett Simonon uses, which is literally the softest lining I’ve felt—and I own a couple of Hanovers and had some Florsheim Imperials, a pair of Alden Indys, and too much more. Also helping is the steel shank, the piece of metal placed beneath the insole to create reassuring arch support. The combination makes for a supportive, comfortable experience.

Fit, Sizing, and All That

Sizing, with any boots, is always a concern. Luckily, Beckett Simonon’s website provides a fit guide that takes into consideration factors including your size in sneakers, dress shoes, and more. It’s not perfect, but it should serve most people fairly well. I mainly wear a 10.5 D on most occasions and my foot is average to borderline chunky, and Beckett Simonon’s Gallagher at size 10.5 fits great.

It all goes back to their last. While it’s vaugely dressy, it provides plenty of space for your toes, a confident, fitted feel on the middle of your foot, and a tight heel that makes for a very secure ride. It almost feels like a combination last, which is a last where the heel of the last is smaller than the forefoot. I guess if I had to compare sizing/feel, it’s reminiscent of an Alden Indy or a really nice dress shoe; when you slip on the boot, it makes a nice, vacuum-like suction sound.

So What Makes Them Imperfect?

I know I’ve been writing a love letter to my boots, but I have to get down to some less-glamorous details. These are not the perfect pair of boots. Since Beckett Simonon is a growing company, though, and are always changing and improving their product line, so caution: a lot of parentheses are going to be in play below!

To start, the Argentinian calfskin they were using at the time tends to make some ghastly Chromexcel lottery-like break over the vamp. I’m not a fan; it’s kind of like buying a car and getting a big door ding right on a body line. You can’t help but look at it and just die a little inside. (The current Gallagher uses an Italian calfskin that I’ve yet to try, so this may not be reflective of the current product).

The next two imperfections are a little more personal preference as opposed to obvious flaws. The Blake construction method, although a popular and re-soleable one, generally has a shorter lifespan than another: the Goodyear welt. Finally, while the leather sole does the job fine and does look nice (and I swear, they smelled like bacon before they got beat, it was amazing), a rubber outsole would have made this boot more usable in more adverse conditions and would have fit the boot’s personality more. (Beckett Simonon’s Gallagher has a number of other leather options, including a pull-up leather and a suede. These alternative options have their SBR rubber soles.)

I think the boot’s biggest weaknesses are integrated into Beckett Simonon as a company. They have a long wait time of about three months, with the COVID-19 pandemic pushing my boot’s delivery date about a month further. Despite Beckett Simonon recently sending emails about trying to make their production times faster, they still require a great deal of patience. Good thing is, they provide you some fun reading material bi-weekly about the shoemaking process via email as you wait for your boots.

Lastly, their pricing is more than a little deceptive. Upon visiting their website, you’ll be greeted with a 20% off coupon upon signing up for their newsletter. Strangely kind, but a not-unusual practice in today’s market. However, when you check out their products, you’re going to see a line across their “traditional retail” price and their actual made-to-order price next to it. I’m going to give you a big hint and say: they were never worth four hundred dollars. While they’re definitely a good value around $200 and I do love my Gallaghers, this is an issue I have with many direct-to-consumer companies: the misrepresentation of their product’s value. Don’t let the marketing fool you, kiddos!

If You’re Looking to Get Started With Boots, These are a Great Place

The hobby of boot/shoe collecting is growing, and we all have our own starting point. I’d say the Beckett Simonon Gallagher fills the starter boot niche for almost anyone. Sure, I can follow the reasonable advice of r/goodyearwelt and look for seconds of X good brand, I also want to feel special when I do something for the first time. You know what sounds special? A boot made for you, handcrafted in a lovely city in Colombia.

It does not sound quite so glamorous to keep stalking eBay or Sierra Trading Post to look for Red Wing seconds that may not even fit. These boots aren’t just the standard boot you order and expect in two days; they’re an exercise in prolonged anticipation. It’s not the hunt, it’s not the “eureka” moment. It’s the wait for the upcoming journey you’ve never realized you were about to take.

The Stitchdown Final Take

My objective take Beckett Simonon’s Gallagher boots is this: if this is your first endeavor into quality footwear, these are a very good buy. I know there are better brands, and I know there are superior construction methods. And yes, all the forums will have the objective nerd screeching “MEEEEEERMIIIIN!” on the newbie post of “what’s a great boot for 200 bucks?” But this is a darn good boot. It’s never going to be perfect, but the first step is always the one that you could have done better, but never regret.