Frugal & comfortable men's boots for footwear delinquent

December 27, 2019 11:45 AM

I need to up my game with shoes and boots this coming year. But I've gotten lazy over time about wearing only the most comfortable shoes possible: athletic shoes, slippers, flip flops [lol], Crocks [double lol+tragic], occasionally some chukkas.

Because I telecommute there isn't a need to dress for work. Still, I'd like to move into this century re my fashion sense.

I love these types of boots (although some of the prices are daunting).

But the thing is when I look at those pictures my feet start screaming.

I've done some searches on AMF re this query but the posts are older with some dead links.

I'd appreciate any suggestions and recommendations that cover my criteria: A budget of about 300 bucks tops and a boot that won't kill my feet -- and heels.

posted by zenpop to Clothing, Beauty, & Fashion (13 answers total)

I just got a pair of duckfeet boots - you can see how they can be styled here. (I’m a woman, but their shoes are unisex.) I’ve surprisingly gotten a fair number of compliments, from both men and women. I’ve got very wide and problematic feet but these work well - I even wore them hiking over the weekend. I also own two pairs of Kodiak boots (also unisex) which are also suitable for work and hiking, but are on the narrower side.
posted by umwhat at 12:06 PM on December 27, 2019

Well, there are no shortage of men's boots on the market these days in that style, so you have tons to choose from... From classic brands like Wolverine to Chippewa to Danner to more trendy brands like Astorflex to Rhodes to Rancourt and Co, etc, etc...

What about something like this? The soft leather upper and leather insole should conform to your foot after some time and become very comfortable.
posted by Jacob G at 12:11 PM on December 27, 2019

I own and wear a good number of boots from those linked and similar boots, and really have no issues with heel pain unless I'm literally spending my entire day on my feet.

Most of these boots that you linked are going to be constructed the same (stacked leather and wood for heels or rubber sole and cork with leather heel leather heel cup), so there's no specific brand that's going to make a difference. With that said what you should look for is the best fit.

My suggestion is that you look at a boot in the $200 range and then evaluate if you need to spend $100 on inserts.

Some good candidates around this price point are;
Thorogood - Beloit and Dodgeville (Look for a sale on Milworks or Huckberry)
Chippewa - Service Boot
Red Wing - Iron Ranger 2nds (look for them on Sierra Trading Post or Nordstrom Rack)
LL Bean - Katahdin Iron Works
Allen Edmonds - Higgins Mills
posted by nulledge at 12:11 PM on December 27, 2019

Additionally, here's a great look at how boots are constructed. So, maybe consider Thursday as well?
posted by nulledge at 12:22 PM on December 27, 2019

I have two pairs of Frye boots (; while they retail for close to $300 I have not infrequently seen them on sale for closer to $100. Seems like they go through a lot of different styles so sometimes places are just blowing out one style they're not making anymore. Anyway, both are similar to some of the things you've got in your link, like the Iron Ranger or the Frontier Boot, both are snazzy enough to sharpen up a pair of jeans, wear to work, etc.

They're also comfortable enough to wear all day without difficulty, though if comfort were my absolute priority I'd want something that didn't come up very high - things feel a lot free at or below the ankle - and while I think they're hit or miss stylistically, chelsea boots might be right for you.
posted by entropone at 12:26 PM on December 27, 2019

I recently went and tried on a bunch of boots at REI, including swapping the generic insoles out for Superfeet insoles that they stock next to the shoes. (I keep the same insole brand in my ski boots, where they've held up for literally 20 years at this point with seasonal use.) While I ended up buying boots that didn't require an insole swap, I was surprised to find how effective insoles were capable of transforming the comfort level of boots like Blundstones for me. But you need enough volume in the boot for a thicker insole to fit. IMO this is one of those things worth shopping for in person if you're going to be evaluating a boot / insole combo.
posted by deludingmyself at 12:41 PM on December 27, 2019

Seconding that replacement insoles can really transform the comfort of a dress shoe. For various reasons, I had to wear leather shoes with a specific look for a job that required a lot of walking and while the shoes I'd gotten (a pair of Panama Jacks) would kill my feet with the leather insoles they came with, with replacement insoles they were very close in comfort to your average athletic shoe. I prefer SuperFeet insoles these days, but even bog-standard Dr. Scholls will be better than nothing.
posted by Aleyn at 1:02 PM on December 27, 2019

Thanks, everyone, some excellent suggestions here.

And yes, I'm familiar with insoles and own a couple of sets of Superfeet. I will definitely put them to use.
posted by zenpop at 1:37 PM on December 27, 2019

Blundstone are incredibly comfortable in terms of being built on a good last that is foot shaped while also being fashionable. I find them a better fit for my wide feet than Duckfeet personally.

Aetrex insoles are a godsend for me for workout shoes, ski boots etc. If you have any foot pain give them a try. I find they make most shoes fit me somehow even ones that seem too small, possibly via magic. Cheaper than orthodics but find a dealer and stand on the machine thing to get a proper fit. I wear them in a totally different size than my actual shoes.
posted by fshgrl at 2:16 PM on December 27, 2019

Dropping in to suggest Blundstones. They meet your price criteria, are super comfortable, and well made. A favorite of journalists who may have to be on their feet all day and look appropriate in different settings.
posted by thenormshow at 3:14 PM on December 27, 2019

Fshgrl and thenormshow -- what about these Blundstones. I like laces. Thoughts?
posted by zenpop at 5:10 PM on December 27, 2019

I (a woman with large feet with extra bones) also only wear comfortable shoes. I consider boots to be very comfortable, but they may require breaking in and/or additional insoles. My default boots are Dr Martens, which are not cheap, but I've had the same pair for many years.

My recommendation is to break boots in by wearing them around the house -- then the moment something starts to hurt you can take them off / put on more socks / tape up your feet. Then cautiously start wearing them only on short excursions.

(I recently bought my first pair of formal high-heeled shoes (actually medium-heeled) in about 20 years, and boy am I glad that the first time I wore them I could spend a lot of time sitting. Next time I'm taking backup sandals.)
posted by confluency at 8:24 PM on December 27, 2019

(Also, I love the Crocs sandals that don't look like Crocs. Very comfortable, washable, and not hideous. I recently found a really nice design, and got two pairs in different colours, one of which I use as house shoes.)
posted by confluency at 8:30 PM on December 27, 2019