Comfy Dapper Dress Shoes?

March 24, 2023 12:33 PM

I'm looking for dapper oxford-like dress shoes to wear to conferences that won't wear out my feet wandering the city the conference is if I end up walking a mile. So cushy soles and/or lining but also snazzy on the outside please!

I'm a women's 7 or 7.5. I've been looking in both the women's section and the kid's section for this in case a large shoe meant for boys would fit me. I don't think most men's shoes come in my size, but if you find one that's fine too.

posted by azalea_chant to Clothing, Beauty, & Fashion (15 answers total)

I'm not sure what they've got for women, but Clark's Unstructured is my go-to for this exact purpose for men's semi-dressy shoes. That might be a useful point of reference even if they don't make exactly what you want.
posted by Alterscape at 12:49 PM on March 24, 2023

I always recommend Fly London shoes. They are shockingly comfortable - the ones with rubbery wedge soles are the ones I've bought in the past, and they honestly feel like sneakers. They have a few Oxford and Brogue type styles.
posted by nouvelle-personne at 12:57 PM on March 24, 2023 [5 favorites]

I am big fan of Tricker's — they are very spendy — but will last a lifetime. But you may find your size on their outlet site for significantly less expensive! I have issues with my feet and they are the most comfortable shoes I have ever worn.
posted by Lescha at 1:22 PM on March 24, 2023 [1 favorite]

Rothys knit shoes are very comfortable- they make a loafer if you're open to something more casual. I routinely walk long distances in them (though also walk long distances in heels, etc, so YMMV...I think if you regularly walk around the city maybe most shoes become more comfortable).
posted by pinochiette at 1:26 PM on March 24, 2023

I'm not super happy that they seem to only retail through Amazon, but the comfiest work/dress shoes I've bought have been through U-Lite. These brogues are my favorite, and there are lots of good color combos. After about a season of wear, the outermost layer of sole started peeling away, but it's easy to glue back down. I've also had good Clarks brogues in the past (and a gorgeous pair from Julia Bo, but I would call those the opposite of cushy), but I've bought two pairs of U-lite dress shoes with leather uppers, and they've been consistently wearable out of the box and not as cheaply made as you might expect from the vendor/price point.
posted by quatsch at 1:30 PM on March 24, 2023 [1 favorite]

Response by poster: Extra info: I'm an American so US based sites are best. Bonus points for monk straps.

Thanks!
posted by azalea_chant at 1:35 PM on March 24, 2023

Ecco shoes have fairly comfortable soles. I know Cole Haan used to make dress shoes with Nike Air soles on them as well.
posted by any portmanteau in a storm at 1:54 PM on March 24, 2023 [2 favorites]

I haven't tried this myself yet, but keep wanting to try Tomboy Toes
posted by kbuxton at 3:02 PM on March 24, 2023 [1 favorite]

Yeah, I've walked many many miles in my Cole Haan "Originalgrand" oxfords very comfortably. They also look good forever. They are pricy but often go on sale.
posted by LeeLanded at 4:46 PM on March 24, 2023

I am a big fan of Børn. True to size, well made so comfortable.

Miz Mooze are progressive funky and extraordinarily comfortable. Even their heels. High quality. Can be a bit spendy.
posted by porpoise at 6:44 PM on March 24, 2023 [2 favorites]

Just fyi, I have Miz Mooz "Letty" Oxfords and they are gorgeous... but not as comfortable as I expected. The leather is quite stiff. I wear them for a day in the office but I wouldn't want to spend a whole conference walking around in them.
posted by EllaEm at 10:42 AM on March 25, 2023

These circus NY crushed velvet loafers in jewel tones colors are pretty neat.
posted by erattacorrige at 11:50 AM on March 25, 2023

Response by poster: I went to the consignment store and found some used cole haans though the tomboy toes also especially appealed but it was nice to try on the cole haans in person and I got lucky that they were there. Thanks all!
posted by azalea_chant at 6:17 PM on March 25, 2023 [1 favorite]

Pikolinos make the most comfortable and durable shoes I've ever worn. I have pair of boots I get compliments on every time I wear them and people can't believe they are 5 years old. I've never done anything to care for them either (wax polish etc). You'll want to look under loafers and laces. They have a few Oxford like options.
posted by CleverClover at 7:30 AM on March 26, 2023

Adding this for the benefit of posterity: Julia Bo has lots of great styles! And you can design your own! Downside: they're all made to order so you'll have to wait a few weeks for them.
posted by orrnyereg at 8:08 AM on March 27, 2023 [1 favorite]