How to find comfortable ankle boots?

December 29, 2017 4:50 PM

I'm having trouble finding comfortable women's ankle boots. Any suggestions? Any shopping tips? Am I doomed to discomfort if i continue hoping for one with a small heel?

I pretty much wear Sanita (formerly Dansko) clogs all day every day and would like to mix it up a bit. I'd like to be able to hop on a bike, walk around the city, and chase a thirty pound toddler when necessary, while still looking professional.

For months, I have wanted a certain pair of boots based on seeing them in person and hearing they were comfortable. Some generous family member gave them to me as a gift. But in the area where the toes hinge, especially on one foot, it is pretty tight. Everywhere else, though, it's wide enough, so I'm not confident that I should just size up to a wide, and anyway, the wide is pretty much not available in size 9.5 anywhere.

Previously, I tried buying these shoes on Ebay -- similar form: ankle bootie with unobtrusive zipper and small heel. Those felt like they fit, mostly, but after a day, I really could not walk. They kind of tilted my foot in slightly while not allowing the big toe to spread out to carry that weight (if that makes sense).

Can anyone suggest something comfortable that looks similar, and is similarly durable, and not too expensive? (The price range is a little flexible, as I am not averse to buying used. But the thing about that is that often you can't return them or waste a lot on shipping.)

All ideas appreciated!

posted by slidell to Shopping (30 answers total)

I have the Naturalizer Cassandra for my very wide feet: the upper is soft and doesn't push my big toe inward, and I can easily run in them.
posted by batter_my_heart at 4:56 PM on December 29, 2017 [1 favorite]

Basels take a little while to break in. Keep wearing them for short stints and I think you will find that the toe hinge will loosen up and fit better. Once they're broken in, they really are about the most comfortable thing I've ever worn on my feet. I am on my third or fourth pair and just keep ordering them instead of looking for new shoes.
posted by peanut_mcgillicuty at 5:00 PM on December 29, 2017

I have a pair of Lissie by Miz Mooz that are super comfortable and have held up well for the past 4 (maybe 5?) years. The sole is rubber and the toe box is generous for my wide feet.
posted by vespabelle at 5:09 PM on December 29, 2017

Auditions Shoes has a lot of shoes and boots in hard to find sizes.
posted by Nancy Lebovitz at 5:25 PM on December 29, 2017

I know exactly what you mean about the leather being stiff and feeling narrow around the toe. (I have a bruise on the top of my left big toe right now from a new pair of boots.) There might be a brand or price point where this doesn't happen, but I have bought many similar boots from the same or similar brands, and as far as I can tell, it just takes breaking them in, which takes time and wearing with high-quality or otherwise thick leather. I'm still working on a pair of Mexican-made Fryes that are literally like 3 years old and an eighth of an inch thick.

I did have some success stretching a particularly bad pair of booties by filling a plastic baggie with water, squeezing that down into the toebox of the shoe, and then freezing the whole thing. They were unbearable before that, but after, it only took one or two wears before they became one of my go-to-pairs.

My husband's technique is just to wear them every single day, especially in the rain or snow. This does work quickly, but significantly shortens the lifespan and cosmetic appeal.
posted by slenderloris at 5:31 PM on December 29, 2017 [3 favorites]

I've had good luck at torrid for wide booties.
posted by Ms Vegetable at 5:53 PM on December 29, 2017

Response by poster: Basels take a little while to break in.

it just takes breaking them in

Really? This is hopeful. But how do I know the difference between shoes that aren't comfortable now but will become comfortable, and shoes that just aren't a good fit for my feet?
posted by slidell at 5:58 PM on December 29, 2017

They're not cheap but I love Born shoes, and they have a similar look to what you seem to like. I need lots of room in the toe box too. Keen's are another brand that work well for me. I have gotten Born shoes discounted at Ross and TJ Maxx, but that's easiest if you have a common shoe size, YMMV.
posted by selfmedicating at 6:20 PM on December 29, 2017

I have a wide "toe-hinge" area, and I've had success with two booties, a Merrell one and a Born one. The specific Merrell was discontinued (they always freaking do that) but I wore the shit out of it for 4 years until the zipper broke and it was too expensive to fix. The Born one is Trinculo (available and on sale) - it was uncomfortable for the first day but immediately stretched to be comfy. I don't know if maybe I'm buying slightly lower quality leather that's stretchy, but caps use at a few years. I bought Frye boots once that I could NOT break in and caused me a fair amount of pain.
posted by permiechickie at 6:21 PM on December 29, 2017 [1 favorite]

I highly recommend these. I have walked ten miles in them and still felt good afterward. I generally wear a 10.5, and have a wider foot, especially in the forefoot. I wear a 42 in these, so I'd say you'd be good in a 41. They were on sale at 6PM recently.
posted by sulaine at 6:30 PM on December 29, 2017

They kind of tilted my foot in slightly while not allowing the big toe to spread out to carry that weight (if that makes sense).


It’s worth trying a wide (either in this boot or similar style.) I have a wide forefoot but standard/narrow heel, so wide isn’t always perfect, but it does solve the issue you describe. If you try both, you can kind of tell the difference between leather that needs to be broken in to move and shape to your foot, and a shoe that is simply not constructed to accommodate your foot. That design is not going to be as comfortable as a clog, but you shouldn’t feel tilted in and cramped.
posted by kapers at 6:43 PM on December 29, 2017 [1 favorite]

I have slightly wide toes compared to the width of my heels, and my Tsubo Felecia booties are some of the most comfortable shoes I've owned. They are sold out most places but pop up on ebay occasionally. I lost mine in a move recently and am pretty bummed. With other leather shoes that have been a little too narrow, shoe stretch spray has helped a lot, as has walking through a muddy garden for hours (not really recommended).
posted by a moisturizing whip at 6:49 PM on December 29, 2017

My practice for this sort of thing has been to go to zappos.com, use their filters to find comfortable footwear with the right heel-height, etc., and then sort by average customer review and read all the reviews, making particular note of those reviews by people who have issues/concerns similar to mine. I buy 3 or 4 pair with my credit card, try them all on, pick one and return the rest (and, of course, get my money back). If none of them fit I'd return them all and try again, but so far that hasn't been an issue.
posted by bunderful at 7:11 PM on December 29, 2017 [4 favorites]

I have wide feet, but they are short (size 6W). I have these La Canadienne boots, which I bought on sale a few years ago. They fit right out of the box, no fussing around with breaking them in. This brand is pricey but I paid around $120 for these (not the $250 quoted there) and if you dig around you can find similar or cuter ones of this brand for much cheaper (like these ones from Amazon). I've heard other good things about this brand. Good luck.
posted by sockermom at 7:29 PM on December 29, 2017 [4 favorites]

Thirding the Born recommendation.
posted by Autumnheart at 7:29 PM on December 29, 2017

Is there a The Walking Company store near you? I perked up when I saw the Dansko brand name--TWC sells Dansko brand footwear. I like the Walking Co. brand, Abeo, myself. All my footwear comes from that store now. They sell other brands also, including Born. One thing about them is that they sell orthotics that fit most shoes (I think) and are customized (metatarsal, neutral, etc.) based on an in-store foot reading... thing. (Sorry, don't know the official term.)

What I like about them is the return policy. You of course can return a pair of shoes if they are unworn. But if you do wear them out and you find them uncomfortable, you can return them for store credit (to be used at the time of return). I can't quote how long they give you to do this off the top of my head, but I can verify they honor these policies.

Also, I've gone to their store to diagnose a pair of pain-inducing boots that I bought elsewhere. They stretched out the toe box for me and also recommended a thinner orthotic, which helped!

They have a website here: https://www.thewalkingcompany.com
posted by artful at 7:31 PM on December 29, 2017 [2 favorites]

After a long and frustrating hunt this fall, I finally found a pair of boots that work for me - Blondo Liam’s (sorry I can’t link, I’m on mobile). I ended up going up a half size because they were narrow, but I found I actually like having the extra room and that I can wear them with thick or thin socks. They’re suede but Blondo claims they’re waterproof and so far they are holding up beautifully with frequent use, exposure to rain/snow, and my generally being rough with footwear. I recommend checking them out as an option! Good luck with your quest.
posted by carlypennylane at 7:39 PM on December 29, 2017 [1 favorite]

I love the look and feel of Sam Edelman ankle boots, which are available on Zappos. I have them in black suede and brown leather. link
posted by JenMarie at 8:16 PM on December 29, 2017

Another vote for Born. They are the most comfortable boots I’ve ever worn. You can find them on sale in January. IF I could run a marathon, I bet I could do it in Borns.
posted by raisingsand at 8:53 PM on December 29, 2017

I love my Ariat ankle boots. They are nearing vintage status, but these look similar
posted by rw at 9:29 PM on December 29, 2017

Forget the Lucky brand boots if you have bigger feet, like a lot of mass produced womens brands they don't size up in width appropriately for the length so your toes get crushed. If you want to see what I mean compare them to a similar length mens shoe then consider that women have ~wider~ feet than men in general. It's super annoying and why models all have hideous bunions.

Anyway.... I find northern European or Canadian brands (La Canadienne, Sorel, Born, Clarks) in general fit me 100% better than Spanish or American brands (Sam Edelman, Lucky, Camper, Pikolinos). The average womans foot is just a lot bigger in those populations so you will be closer to the middle of the sizing curve. One US brand I do like is Aerosoles, they aren't the most stylish or best quality but for $100 they will generally not shred your feet and they last as well as any $100 shoe. Long Tall Sally still carries womens shoes in large sizes and might go down to a 9.5, and they are better quality.
posted by fshgrl at 10:04 PM on December 29, 2017 [1 favorite]

Anecdata: I bought a pair of Lucky booties about 10 months ago, albeit with a slightly taller heel. I have wide feet. They hurt if I wore them for more than an hour or so, so I only ever wore 'em grocery shopping. But in the last few weeks, I finally succeeded in breaking them in, and they now are incredibly comfortable. Two lessons: it is possible with Lucky booties, and, you may well not be willing to wait months.
posted by estlin at 10:42 PM on December 29, 2017 [1 favorite]

I love my Teva de la Vina boots. Comfy, waterproof, have walked miles in them. I also need a wide toe box and found these were slightly snug in that area at first but after a week or so with thick socks, they were perfect. I've had one pair that's carried me through two years of variable weather and they're still going strong! Also, if you are a fan of Dansko, they make boots, too.
posted by stillmoving at 1:27 AM on December 30, 2017 [1 favorite]

you might like Blundstones. They come in a lot of different colors, shapes, and sizes-- they run about 200 dollars per pair, but they are extremely durable. I've worn mine daily for 9-10 months/ a year (and I walk about 10km a day) for the last five years. Super comfortable once broken in.
posted by atetrachordofthree at 6:04 AM on December 30, 2017 [1 favorite]

Seconding Blundstones. Their half sizes are wides, fyi.
posted by you must supply a verb at 8:02 AM on December 30, 2017

But how do I know the difference between shoes that aren't comfortable now but will become comfortable, and shoes that just aren't a good fit for my feet?

I don't think I have a good answer to this :(

Since you've already worn them and therefore can't return them anyway, I'd give the freezing treatment a try if you want to accelerate things, or else just wear them in shorter bursts. It's certainly possible that they're just not right for you, but I'm not sure how to tell that without breaking them in first.
posted by slenderloris at 12:40 PM on December 30, 2017

The aesthetic isn't quite as sleek as the ones you've linked, but Sanita does make boots. That one's sold out in your size, but I thought I'd mention it anyway, since you said you're not averse to eBay.
posted by dizziest at 3:29 PM on December 30, 2017

I also spent a while searching for comfortable ankle boots and eventually settled on these Jack Rogers boots.

These look similar to the Sam Edelman Petty boots, but I found the sole of the Petty boots to be too hard, and it hurt the part of my foot just below my toes. The heels on these are not too high, and I put some Foot Petals in mine to make them even more comfortable. I have had good luck wearing these for extended hours.
posted by jasminerain at 4:10 PM on December 30, 2017

I've had good luck with Ecco ankle boots, especially in soft material like nubuck leather.
posted by neushoorn at 4:25 AM on December 31, 2017

I literally just got these and have been wearing them nonstop. They are super comfortable albeit a little too wide for me, but I don't mind (and I have narrow feet).

I also have a pair of Born booties I love, but they are older.
posted by hrj at 12:38 PM on January 5, 2018