Looking for super-comfortable mens' boots. I can shop in NYC or online.
March 24, 2015 10:32 AM   Subscribe

I need to find some super-comfortable mens' boots. Looking for boot recommendations, as well as places to shop. I can shop in NYC or online.

I need to find some comfortable mens' boots. I have a foot issue (Morton's Neuroma), so the boot must have a nice, roomy toe box. It must also be capable of accommodating an orthotic or insert. Finally, it needs to be durable enough to wear in the rain, because I live in NYC and it rains here.

My priorities (in descending order) are : comfort, durability, and style. While style is not as important to me as comfort or durability, it is still important. I've been wearing these Timberland boots the last few years, and I really like how they look : simple, black, and almost dressy. I would like to stay with that kind of style, if I can.

Looking for any kind of recommendations you may have : brands, models, places to shop (in NYC or online), helpful websites, that kind of thing.

Comfortable footwear is important to me, so I'm willing to spend a fair amount of money on these.

Thank you for your help.
posted by evil otto to Shopping (13 answers total) 4 users marked this as a favorite
I have had a pair of these men's Caterpillar boots for about fifteen years, and they've held up beautifully. Took an orthotic no problem. That particular style might not be dressy enough for you, but they have a ton of styles, of a variety of waterproofness. (The plain leather ones handle rain just fine, but I've never gone wading in them or anything.)
posted by restless_nomad at 10:54 AM on March 24, 2015

I have a pair of Clarks that meets your requirements - especially comfort - and they have other suitable models. They have several locations in NYC.
posted by Mr.Know-it-some at 11:00 AM on March 24, 2015

Do I have a tip for you! (Or at least, do I have a tip that involves saving some money on a very expensive boot.)

I have a wide forefoot and need either a roomy toebox or stretchy leather. Tricker's boots are incredibly durable and their country line is very wide.

My suggestion would be to go to Graham Fowler and try on the Stow and the Burford, then order from Pediwear. Normally I would not want to do a small business out of money, but srsly, the mark-up on those Stows is nuts.

That's if you're really planning to break the bank, of course.

One thing: I notice that restless_nomad is recommending a style of boots that he bought 15 years ago. Unless you can confirm that the factory and production standards have not shifted (and they have shifted almost everywhere, including at remaining US makers like Allen Edmonds - I own both 1990s and 2010s AEs, for instance, and the quality is WAY lower now) examine the boots in question carefully. Sadly, boots from 15 years ago are almost certainly way, way better made than anything from the same company today.

You could also visit a Red Wing shoe store in NYC and look at their heritage shoes. I have no personal experience with them, but they seem to be built on wide lasts.

Some of the Wolverine 1000 mile boots (only the US-made ones - check carefully, the Chinese ones are super, super overpriced and the whole thing is a bait-and-switch) are great - they have a slightly roomy last and the leather is very soft and molds well to your feet with wear. They have flat leather solves, but you can take them to any shoe guy to have either a vibram sole added (he can knock off the original heel) or a chunky sole-cover put on.
posted by Frowner at 11:07 AM on March 24, 2015 [1 favorite]

You want the Red Wing Gentleman Traveler, probably in black cherry. Treat them regularly with Sno Seal and they will last you a lifetime.
posted by rossination at 11:08 AM on March 24, 2015

On preview: Frowner's recommendations are also great!

Although restless_nomad is she.
posted by rossination at 11:09 AM on March 24, 2015

Sorry restless_nomad - there was no reason to assume gender, especially since I don't use he pronouns myself and yet....I wear men's boots!
posted by Frowner at 11:13 AM on March 24, 2015

I have some Red Wing Iron Rangers, and they're wonderfully made and really comfortable after a break-in period, but the sole is smooth, so not great for snow and ice. Those Gentleman Travelers would be great, I bet. Try to get into a store and try them on, though.
posted by Huck500 at 11:14 AM on March 24, 2015

I just got a pair of these and think they're great.
posted by supercres at 11:14 AM on March 24, 2015

If you can, go to Harry's Shoes. They specialize in walkable shoes and boots and will take the time to help you get the right fit. Prices are mostly comparable to online, which is a plus.
posted by Mchelly at 11:20 AM on March 24, 2015

If you see a pair of boots you like and they have a smooth leather or rubber sole, you can take them to a cobbler and ask to have one of two things done:

The cobbler can glue a robust textured sole-cover on the whole of the front of the foot - a variety of textures are available, from slightly-coarser-than-sandpaper to deeply textured like a work boot;

Or he can knock the heel piece off and attach an entire vibram workboot sole. This will of course slightly bulk up the sole of the boot, but most smooth leather soled boots have thin soles to begin with.
posted by Frowner at 11:30 AM on March 24, 2015

if you need a roomy toebox, steel toes may be the way to go. In my experience, steel toed boots have a taller toe-box that won't deform with age. As far as brands, Red Wings have been good to me. I've got a pair I've worn regularly for 20 years, which the soles have just about worn smooth on, and the uppers are still holding up well with only infrequent mink oil treatments.
posted by cosmicbandito at 12:47 PM on March 24, 2015

I asked a recent AskMe about buying men's boots in NYC. It might be of some use to you.
posted by Conrad Cornelius o'Donald o'Dell at 10:39 PM on March 24, 2015

Response by poster: Thank you all for the help! You've given me some great leads. I will update the thread once I've made a purchase.
posted by evil otto at 9:42 AM on March 25, 2015

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