Let me start by saying that I shopped long and hard before settling on these boots. I hit junior high at the peak of the Doc Marten trend in the late 1990s and wanted something similar but more refined. Docs are too bulky, a little youngish for me, and they almost look too much like work boots. I'm in that intermediate phase between PhD student and professor and I've got to look the part! These boots are just right. They look great with jeans and khakis alike and the black cherry color gives them a little extra class that distinguishes them from the common work boot. Check out the "customer photos" I posted on this product page. It was pretty common in my boot search to find guys who just simply wanted to know how they looked with jeans, so I posted a few pictures with Levi 527s -- ordinary boot-cut jeans (not the hipster stuff you find on most of the style forums). The photos also show how the red really shines on the black cherry color (but not too much like the ugly burgundy dress shoes your dad used to wear).

The leather is absolutely top quality, unmatched by anything else I've seen in this price range. The only comparable leather I've seen was on a pair of boots I came across in a shoe store in Oxford, England, but they started at around 400 pounds ($800 at the time!). The leather in the toe and around the foot is really thick and stiff -- very durable stuff. The leather around the ankle is soft and supple, even when the boots are brand new. I didn't have any problems with the tongue cutting into my foot either: it seemed pretty soft from the start. With that said, the boots were a bear to break in. It took several days of pretty intensive walking around the city before they started to feel noticeably softer, but I managed to make it through without any blisters (always a plus!).

They also have a real leather midsole (the light-colored layer in the photo) and a low-profile rubber outsole with minimal tread. I like the look of the pure leather sole (as seen on the Wolverine 1000 Mile Boot), but it's just not practical. Leather soles are slippery as heck on nearly every surface and they're a nightmare if you happen to get them wet. The Gentleman Travelers have the best of both worlds. They almost look like a leather-soled boot but they have the functionality of rubber. If you're used to Docs or common work boots, the Gentleman Travelers will feel lower to the ground, but the heel is high enough that you still feel a little taller.

Now a little bit about the sizing. This is tricky with these boots, especially if you order them online without trying them in the store first (as I did). Most reviewers (both on Amazon and elsewhere) have said that you need to size down by half or a full size. Half is probably closer to the mark. A full size down seems a stretch. But let me recount what I did so that you can decide where you fall. I'm normally a size 9.5 but several of my shoes are 10. I wear Allen Edmonds dress shoes in a size 9D and they fit just right (though one reputable clothier measures me at a 10B -- erroneously, in my opinion). Given all of this, the correct size was probably 9 in the Gentleman Travelers: half a size down from my normal shoe size. But I wanted to put insoles in them. They come with a built-in leather insole but with little support. I'm a big fan of Super Feet and planned to use some with these boots. I ended up ordering the 9.5 with the hope that the insole would make half a size difference for the perfect fit. I was right. When they arrived, I tried them on as they came (with no insoles) and they were a little loose. Then I tried my Super Feet, the green color, and they were a little tight in the toe area. As it turns out, the light blue colored Super Feet are the same as the green but a little thinner: these were just the ticket. One more thing on sizing, though. They're a little sloppy in the heel. The first few times wearing them my heel rubbed pretty bad, but they seem to have gotten better over time, probably because the sole is loosening up and the leather around the ankle is forming to my foot. I think for most guys the larger heel area would be OK, though. I have skinny ankles that probably make the heel looser. I bought a pair of heel pads to snug them up a little but they've almost become unnecessary as the leather has softened.

Overall, I'm very pleased with these boots. I got them for a pretty good price (I think) at $247. If you can't find your size and color marked down like I did, go find some in a store, try them on, and come back later to see if yours get marked down. Probably worth the price even at $320, though. Great boot that will last a lifetime!

UPDATE AFTER A YEAR OF WEAR:  I'm still wearing these boots on a weekly basis a year after buying them.  All of the original problems have disappeared: heel-rubbing, stiff leather, sizing, etc.  The leather does indeed form and stretch to your foot if you start out *slightly* snug (but not too tight).  I would also say that the leather finish has held up very very well - I was concerned that the cherry polish would scratch or scuff away.  They do, of course, get a few scuffs and scratches over time, but it hasn't changed the finish.  The leather is dyed all the way through as all quality leathers are and therefore you cannot scratch away the cherry finish.  Overall I'm still as pleased with them today as when I got them over a year ago.  Get compliments all the time, too.