What are some great looking AND super comfortable dress shoes?

August 22, 2017 1:48 PM

So I've got very big trip planned. My last one of those, I bought some dressy hiking boots with solid reviews that I intended to use as my main shoes. The hybrid of looks and comfort didn't pass muster and my feet paid a price. I know that I could just go with standard walking shoes but anything that looks like it could be on Hiker's Monthly, isn't going to be appropriate for a more upscale urban tourism. And I'm trying NOT to lug around two sets of shoes. So IS there anything that does both? I'm willing to spend to make it happen.
posted by rileyray3000 to Clothing, Beauty, & Fashion (22 answers total)

Mephisto?
posted by slkinsey at 2:10 PM on August 22, 2017

Not sure if you're looking for women's or men's dress shoes, as the recommendations might be very different. If you're looking for shoes and not heels, and you're looking for something that looks good but isn't specifically a dress shoe, try Ecco, the Walking Company (Abeo), Clarks, Cole Haan, and some Rockport, Keen, and Merrell shoes.

Most of those manufacturers make both men's and women's shoes. I (man) have problem feet, am going on a long overseas trip where it will rain and needed shoes I could wear with anything short of a suit. I bought these two:
* https://www.amazon.com/ECCO-Hayes-Sneaker-Black-11-11-5/dp/B010RSFPCW
* https://www.amazon.com/dp/B01EKHN8JS/ref=twister_B016KGGPDS

The Hayes ran about a full size too big. I liked them when I got the right size, but they had moderate a roller-type heel, which bugged my achilles (PROBLEM FEET), so I sent them back. The pattern on the Exceed is very subtle in person, they're true to size in men's, super comfortable and I think these are the ones that are going to work for me.

For men's dress shoes, I don't have great recommendations, but you might start with Alan Edmonds (not necessarily as comfortable, but repairable and should last) and Cole Haan (more comfortable).

Good luck!
posted by cnc at 2:11 PM on August 22, 2017

If you're a woman, my go-to for this is Frye Veronica boots. They have been all over Europe with me. They look good with dresses and have kept my feet warm and dry hiking around the Scottish highlands. Drawbacks are: 1) they're expensive and 2) you pretty much have to wear them on all the planes because they take up a lot of room in your suitcase.
posted by something something at 2:24 PM on August 22, 2017 [1 favorite]

I (female) do a lot of city walking. My preferred walking shoes are Cole Haan moccasins for warm weather and Geox boots for cool weather. Since these shoes are made from leather they don't have that "just hiked in from the back country" look and can be cleaned and polished up, but they are still flexible and breathable. The Geox boots are water resistant which is an added bonus. The Cole Haan mocs do require a little breaking in before they're ready for a full day of walking.

My previous favorite walking shoes were HS Trask loafers. They no longer make that style for women but have several options for men.
posted by 4rtemis at 2:40 PM on August 22, 2017 [1 favorite]

I traipsed around Japan (walking several miles a day) in these shoes by Wolky. They were incredibly comfortable.
posted by brookeb at 2:42 PM on August 22, 2017 [1 favorite]

I'm not sure what upscale urban means in your case, but sneakers are hugely on trend right now, so if you like them they're most likely in.
posted by stoneandstar at 2:42 PM on August 22, 2017

I'm a New Yorker who travels s good bit, and I am a devote of the Spanish brand Pikolinos. They are stylish and well made, and very durable. And they are about the most comfortable shoes I've ever worn... I've owner several pairs of boots and flats. I've also converted my partner and my mom. You can find them at most high-end comfort shoe type places. The nice thing is that they have several sole/heel types that come in different styles, so if you find one that works best for you, you'll have a number of options with the same level of comfort.
posted by kimdog at 3:29 PM on August 22, 2017 [3 favorites]

I have these clarks and they are cute and crazy comfortable. The wedge heel is very bouncy, I have happily walked for hours on them.
posted by 5_13_23_42_69_666 at 3:38 PM on August 22, 2017 [1 favorite]

Back when I lived in New York and had a 45 minute subway commute while heavily pregnant (it's the new uphill both ways) I lived in Dansko, Clarks and Born.
posted by chesty_a_arthur at 3:45 PM on August 22, 2017 [4 favorites]

Vibergs
posted by mannequito at 3:51 PM on August 22, 2017

My wife and I visited Toronto last year and both fell in shoe-love with Fleuvog shoes. I bought two pairs (and I hate buying shoes). Seriously, it was like walking into the Disneyland of shoes. They're comfortable, look great and can be purchased online.
posted by Joey Michaels at 4:08 PM on August 22, 2017 [1 favorite]

Blunnies
posted by you must supply a verb at 5:34 PM on August 22, 2017 [2 favorites]

If you wear menswear-type clothes, you might like a pair of Redwing Gentleman Travellers - I like them for this purpose but they are a bit clunky and might take a while to wear in. They're super comfortable, though, and go with many types of outfits.
posted by rossination at 6:31 PM on August 22, 2017

For women's shoes and a style that's truly dressy enough for "upscale urban tourism"--flat ankle boots. I like the Chelsea boot style, but you have lots of choices. Get them from a Euro comfort brand, e.g. Ecco. You probably shouldn't do actual hiking in these boots, but you could do some trail walking.

If the hiking part of the job is non-negotiable, then consider bringing your regular hiking boots + a slim-line pair of dress shoes. Works best for women, because ballet flats take up little space and are dressy enough to pass muster most places.
posted by serelliya at 6:58 PM on August 22, 2017

I swear by Keen's stuff. Vast range, but some non-ugly/non-technical options for both women and men.
posted by Emperor SnooKloze at 8:30 PM on August 22, 2017

I've heard good things about Chie Mihara shoes. I read somewhere that Ms. Mihara used to make orthopedic shoes and that's why her shoes are so comfortable.
posted by Ms. Moonlight at 11:27 PM on August 22, 2017

2nding Blundstones. I've had the same pair for six years, worn them to upscale-ish events and dinners and plays and concerts and teaching etc etc. Also hiked all over rural Southern England and wore them all over London in the same trip, rode a horse on rough terrain, did some low-stakes rock climbing, went to pumpkin patches etc--all in the same pair of Blundstones. They'll shine 'em up for you and condition them for free if you can take them to a Blundstone store. The soles on mine are splitting now, but those can be replaced for free, too. You will not regret this purchase.
posted by Miss T.Horn at 11:57 PM on August 22, 2017 [1 favorite]

Another vote for Clarks. I do a lot of city walking and they've always served me well. They even sell standard walking shoes that look nice and would be fine in most settings.
posted by photoelectric at 3:18 AM on August 23, 2017

Anecdotally, current Blundstones available in the US are *not* the same quality and durability of the Blundies of yore, in kind of the same sort of development that hurt Doc Marten so badly. Caveat emptor.
posted by uberchet at 6:43 AM on August 23, 2017 [1 favorite]

Fluevogs! Definitely fashion-forward, and people always comment on how comfortable they are (there are reviews at the site). I love mine and my husband has 2 pairs that he loves.
If you only want one pair for the whole trip, I'd suggest maybe (depending on your personal style of course):
Men: Michael
Women: Ayn
posted by Laura in Canada at 6:51 AM on August 23, 2017

I would suggest a 6" leather boot in black or dark brown (depending on your wardrobe). I have walked, hiked, & worked in these Timberland boots in all black, smooth leather. With slacks on, they look perfectly respectable. Stay away from their Earthkeeper line--I walked through the soles in 8 months and couldn't get them replaced (not goodyear welt construction, glued on replacement soles were not worth it). Not sure about some of their newer models, either, but that classic customize your own was my go-to boot for years.

(My super wide feet are trying out these boots from Hitchcock Wide Shoes this autumn.)
posted by carrioncomfort at 7:40 AM on August 23, 2017

Response by poster: Probably should have said it but yes, I'm a man looking for men's dress shoes. But a lot of this info is good for women who've had the same question.
posted by rileyray3000 at 5:06 AM on August 24, 2017