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Home » The Vine

The Vine: November 11, 2011

Submitted by on November 11, 2011 – 12:14 PM54 Comments

I need shoes. I’ve been a student for a long time, but now I’m at the point where I can’t wear jeans and running shoes every day. So I need a nice basic pair of shoes I can wear every day. The problem is I also have to wear heavy-duty prescription orthotics.  This means I have to wear flats, and most “supportive” walking shoes are deeply, deeply, hideous. And clunky, expensive, go with nothing, and HIDEOUS.

What I’m looking for is an attractive, comfortable shoe I can walk in and wear all day. Ideally, I can wear them with a skirt, shorts, or pants (but if I have to I’ll settle for just pants). It needs a thick sole and the shoe itself has to be deep, or have a removable lining so I can put the orthotics in. (The orthotics are hard, curved, plastic, to give you an idea of the depth requirements). For that reason, ballet-flat-type shoes are out. I want something I can wear in all weather, but I live in Canada, so if I had to choose I’d pick non-summer shoes. I already have winter boots, don’t need those.

Budget is a concern, but I’m willing to spend money on one pair of shoes that will last years.

Any suggestions?

Flat-foot and fancy free

Dear Fancy,

Try searching Zappos (or Endless, or your shoe site of choice) for Naot, Keen, and Merrell. I have a pair of Keen maryjanes I wear constantly, and a pair of Clarks wallaby-type black shoes that I wear with skirts and pants. There’s a limit to how dressed-up some of these crunchy-ish shoe brands can get, but if you want everyday work-wear shoes that go between skirts and pants, these shoes should fill the bill. Dr Martens has a few sleeker styles now, more than they used to, and I think the Docs-and-babydoll-dress thing from the early ’90s is coming back in, if you want to take a run at that.





  • Coleen says:

    The first thing I thought of were Dansko shoes. I hear good things about those all the time. I also love Sofft and Born brand shoes.

  • Jennifer says:

    Seconding the suggestion for Merrell. I have these, which wouldn’t really work well with dresses or skirts, but are fine for a range of pants, including khakis and jeans. Merrell also makes a lot of different styles which would be dress-friendly, so I’d check them out. That Jungle Moc I linked to is super-comfortable, water-resistant, and are my shoe of choice for running round and doing errands and stuff. Very, very well made.

  • Billie says:

    Danskos. I live in them. They have Mary Janes that are pretty cute and I can walk in the all damn day.

  • attica says:

    Most of my current shoe crop is Clarks, in which my walking commute is done (and I don’t change shoes once at work.) They’re pretty sturdy and deep. The bad news is they overhaul their selections every year, so finding a replacement for the loafers you liked so well is more irritating than is strictly useful.

    Another online resoure for you (and your orthotic-needing feet) would be Foot Smart. I think they started with the nursing-home crowd, but enough of their collection is current, more stylish stuff that you should find something suitable.

  • Beadgirl says:

    I have a pair of Docs that my feet swim in, so I bet they’d fit orthotics. And Zappos has that wonderful free-shipping-both-ways thing, so you can get a couple different sizes to see which accommodate both your foot and your orthotic.

  • Deanna says:

    My friend has smaller feet and lots of back problems, and she likes Ecco and Born. The Ecco website seems to have a few that might fit your needs–nothing fancy, but will get the job done.

  • Schlinkaboo says:

    Love love love and highly recommend Danskos – only shoe I wear. But the insole is not removable and might not work with the orthotic.

    In this case, online shopping isn’t your friend. Find an old school shoe store with expert salesfolk who can find a great shoe for your situation.

  • Jinxie says:

    Another recommendation for Danskos here! They are super comfortable, sturdy, and some of the styles are even stylish (if that’s what you’re going for). They’re definitely on the pricier side but they will absolutely last you for ages.

  • Gladys says:

    Lands End has comfy and inexpensive shoes that you can put orthotics into. Scout the web or sign up to their mailing list for deals, as well. I just got an e-coupon for 25% off and free shipping.

  • jamila says:

    I also have hard-core orthotics. I find Finn Comfort really amazing. It depends if it works for the shape of your foot or the problem you have, I guess. I find I don’t even need my orthotics in Finn Comfort, because Finn Comfort suit my shape/problem exactly! There are a range of styles, all pretty geeky, but they have a few mary janes and oxfords that work for me for work (I work in a corporate office.) I also have a pair from them that look like converse for every day wear. They are, however, very very pricey. I’m also in Canada, so what I do is try them on at a specialized shoe store here, then wait for them to come on sale on Zappos, and then send them to a friend or relative in the States. Cuts the price in half!

  • Lindsay says:

    Try Clarks! I have similar wardrobe issues/needs, and I love these practical-but-still-cute, go-with-everything shoes :) (also on Zappos!)

  • Kay says:

    I second/third Keens and Danskos. I’m a baker, on my feet for 10+ hours a day, 6 days a week, and my Keens have saved my life.

  • CJ says:

    I have the same problem and will be watching this thread for an all-weather solution. But I will share my not-quite-all-weather solution: Skechers makes some very cute shoes – not running shoes but slightly sporty flats – that are deep, soft and flexible, and have removable insoles. They have been my life saver since I started having to wear orthotics. The shape I’ve used over and over is this one:
    and I’ve found it with details like sequins and pretty fabric insets. They’re cheap too.

  • MsMolly says:

    My first thought would be this pair of Keens: They go with everything, are designed for people who are on their feet all day, and look like they’d hold up through all sorts of weather.

  • Jennifer M. says:

    If budget is a concern, I would suggest the Dansko outlet:

    They have a combination of overstock, discontinued styles, and factory seconds. The seconds will have some cosmetic issues which is why they weren’t sold in regular retail settings, but the markings can be very minor (they give examples here:

  • mctwin says:

    I also recommend Clarks if you can afford them. My sister, the Shoe Maven, swears by them and only JUST threw out her old Clarks from a decade ago. Lots of styles that go with many conservative-type outfits. QVC does a great job of showcasing the Clarks brand.

  • Nanc in Ashland says:

    I gotta recommend Beautifeels. Expensive, but worth it. I have a pair that are 15 years old and still going strong (I do get take them to the shoe repair guy every couple of years for new soles.) I have a pair similar to these <a href=

    I also second the old school shoe store recommendation–that’s how I ended up a Beautifeel wearer. If there is a cobbler or shoe repair shop in your are you might make a visit. They can remove any insole and replace it with something that will work with your orthotics.

    Let us know what you find!

  • Nina A says:

    I recommend Taryn Rose shoes. They are really comfortable, and nice looking. Not cheap, but a pair will last for quite a while-2+ years.

  • Nanc in Ashland says:

    Sigh, why can’t I ever get HTML right?! for the Beautifeels. Not as pretty but it works!

  • Kaijsa says:

    I love Campers, and they can be expensive. But they hold up well and have lots of super cute flat shoes with removable insoles. I have some flats (and I usually hate flats) that I’ve outfitted with contoured insoles and have worn tons for three years.

  • Barb says:

    Just a note – Zappos doesn’t ship to Canada anymore. So find brands there that might be of use but don’t get your heart set on anything until you’ve found a Canadian retailer.

  • SarahBeth says:

    I live in Doc Martins in the fall/winter. Granted, I live in New England where its pretty much a requirement to have thick soled shoes, but once they’re broken in, they’re super comfortable and last for a long time. I bet orthopedics would fit in them too.

    Good luck!

  • Kim says:

    Another Dansko wearer here; I have foam orthotics (not hard plastic, but) that fit nicely into a standard clog and a mary jane style.

    You might also want to look into Fluevogs, if they have a store in your city or if someone else carries them. They run the gamut from clompy to pretty, and while they’re comparatively expensive as “designer” shoes, they’re freaking indestructible. I’ve got a couple pairs in the rotation that are more than ten years old!

  • Sarah D. Bunting says:

    Yeah, Campers are great. They can be pricey, and sometimes twee, but I wear shoes hard and my Camper boots are entering winter #7.

  • Isabel says:

    Another Docs fans here – aesthetics are obviously a personal thing (I live for the Docs + tights + skirts thing when it’s warm enough) but they are definitely really roomy and thick-soled, and super comfy. I work as a first grade classroom assistant so I’m on my feet a LOT (non-comfortable shoes are not an option for me) and I’ve never had any problems.

  • Michele says:

    Keen shoes are great, as are the Danskos. I picked up a pair of Jambu ( shoes on sale at REI before we went to Puerto Rico, and they did not let me down with the walking all day. Mine are in the “All Terra” collection.

  • phineyj says:

    I suffer with my feet too and stand most of the day (I’m a teacher) and a friend recommended this shop:

    It’s a UK brand but they will ship overseas. It also wouldn’t surprise me if they opened in other countries at some point — their core market is older people (I was surrounded by 80 year olds when I went to try their shoes) but they normally have a few trendier styles in stock.

    I use inserts as I have planar fascitis but actually I’ve found the Hotter shoes have so much arch support I don’t need the inserts.

  • phineyj says:

    Ah – some searching on their site reveals they have a US subsidiary, if that helps.

  • Rachel says:

    You can also try Sierra Trading Post for a cheaper option–they carry overstock, closeouts, and seconds on a lot of really great brands for greatly reduced prices, and they frequently have sales or coupons, too.

  • cinderkeys says:

    Seconded: The Walking Company. These guys can work with you.

  • tadpoledrain says:

    Seconding Footsmart. Many of their shoes are old-people-ish, but if you poke around, you can find some cute stuff, and get an idea of brands you want to look for.

    No one seems to have mentioned Propet yet. A lot of their shoes are ugly, but they do make some that are cute (especially some mary janes), and they are usually designed for use with orthotics.

  • Brie says:

    Though I’m a UK reader and therefore leery of suggesting any brands, but just a thought:

    Are Chelsea boots popular in Canada? They’re still pretty fashionable over here and might be an idea if you’re looking to tread the practicality/fashion line. Over here you can get really sturdy leather ones which are usually quite roomy and have a decent depth
    (this is the sort I’m thinking about –
    Although they’re not necessarily officewear they do work pretty well with jeans and – depending on your calf confidence – shorts and skirts. Floaty tea dresses, big cardigans and Chelsea boots has been ubiquitous over here for the past few years.

  • Mary Ann says:

    Vasyli makes the kinds of shoes you can wear with orthotics that might be to your taste.

    And, of course, I also wear and recommend Danskos.

  • mel says:

    Naturalizer’s Pursue model has a nice depth; they are on the casual side, but I am on my second and third pairs (black and brown) because I can go all day in them.

  • Laura K says:

    Just mentioning that is the outlet arm of Zappos. No free shipping, but once you know what you want, and they happen to have it, you are in luck. (I’m an all Danskos, all the time lady and am going to freak the heck out when my current clunky but heavenly shoes die.)

  • Sherry says:

    Just an FYI for all of the Dansko lovers out there. They got bought and a lot of people are complaining. Sanita is the original parent company and still sells shoes. My old Dansko’s have lasted forever, a pair I bought after the spin off had died after only year or so.

  • Karen in Japan says:

    I hesitated to try on these Coach Eloise loafers, because I usually carry a Coach bag and unless they give me an endorsement deal, do I really need to be a walking advertisement? BUT they are amazingly comfortable and have a thick insole that you could remove to accommodate the orthotics. I walk several miles a day, so I’m very picky about what constitutes comfortable shoes.

    (Just for god’s sake get the black version, not the one that’s covered with the logo. Enough is enough.)

  • autiger23 says:

    I actually found a new brand while visiting Cardiff this Summer that kicks my former favorite Keens butt. Here’s a link. They are pricey, but they are lasting longer and wearing better than my previous three pair of Keen oxford type shoes:

  • Rebecca says:

    Another vote for Clarks – I like their “unstructured” line. I work 12 hour shifts in a hospital and I can happily wear them for a whole shift (well yes, my feet hurt at the end but they hurt less in those shoes than most others).

  • Laura says:

    There is a specialty shoe store in my city that carries a lot of removable-insole styles for orthotics wearers. They sell a lot of Finn Comfort (expensive! and there are some mary janes and other ok styles amidst the granny sandals).

    Keen: I find that the soles of my Keens wear out quite quickly, although the uppers still look good; I walk a lot, and the rubber is quite soft and grippy and only thinly covers a porous, foamy layer. They are comfy, and very flat, though, so I keep buying them!

    Maybe try Naot? They have a whole bunch of removable-footbed styles.

  • Kimra says:

    Oh man, I should have read this sooner, cause I have a lot to say on the subject! (A similar quest for myself led me to develop a pretty close relationship with our UPS guy earlier this summer.)

    Comfort-wise, I swear by Keen, and specifically the Sienna maryjane. I wore them on city walks, with skirts and jeans, and to work and out to dinner. Ditto the comment above about the soles wearing fast, though — I went through 2 pairs in three years, but I wore them nearly daily during that time. I thought they were discontinued, but they’re now back on the Keen site (with a “new!” label…hmm). I’m only seeing them in black so far, but they used to come in all sorts of fun colors (I had magenta first, then orange).

    In trying to find a replacement, I tried Clarks, Born, Simple, and Patagonia. I ended up with a pair of Hush Puppies in a style that’s sort of hard-core ballet flat — thick sole, but no strap on top. They’re actually *too* deep for my orthotics (so could be a good option for you) but I’ve found the included insert has adapted to my feet pretty well. I’m not sure how comfy the leather ones would be, but I have these: blue Sincerity.

  • Ellen says:

    Try Ariat – footbeds are removable, they’re sturdy (the company specializes in equestrian/riding gear) and their closed-back clogs and boots come in lots of styles that will go with almost anything. I wear their clogs all the time. Born & Keen are also good, and look at Rockport’s stuff as well.

  • Toni says:

    While I’ve never had foot problems, per se, I am a manager in retail (read, on my feet, up and down stairs 8 hours a day) AND I’m pregnant.

    I know that the general instinct towards foot issues is to go flat, I’ve actually found (and read a lot to back me up) that an inch or two in height can actually help posture, and therefore back issues from being on your feel for too long. (I know your problems are foot, not back-related, but it seems like maybe what’s good for the goose is good for the gander, you know?)

    That all said, don’t worry, I’m not recommending 5″ heels, or even kitten heels. The magic combination is that short heel, but wide and chunky. Easy-to-find and not terribly expensive mall brands like Aresoles, Naturalizer, Soffit, that sort of thing. Something like this, or this. Even better, they still qualify as relatively cute, and go great with pants and skirts/dresses, and are year-round.

  • Sarah in LA says:

    I had the most perfect pair of Mary Janes a while ago, and they totally wore out. On my search for a similar pair, I happened upon these:

    They are surprisingly cute for an orthopedic shoe, they fit my orthotics, and I love the velcro strap.

  • JeniMull says:

    I highly recommend Mephistos – they have lots of styles that don’t look crunchy at all. SUPER comfy.

    The price tag is shocking, but try ebay for past seasons, new in box, for around $100.

  • Kate Smith says:

    I had orthotics for plantar fasciitis, and I second the Clark, Dansko, Keen and Merrell love. (I’m on my second pair of Dansko Professionals after five years of hard wear – 4-5 days a week – on the first. Apparently I pronate too. Sheesh.)

    I did have to go up a half or whole size to accommodate the orthotics, so you might look at that part when ordering. I found that once I discovered what my shoe size is with orthotics, I could order online without trouble.

  • australienne says:

    Ok, I can write a novel on this one.

    European brands generally do this type of shoe very well, but the prices can be hair-raising. I’m prepared to spend the money, because a) I can afford to, b) I like to look nice and c) my feet are so awful shoes are the wrong place to save money. That said, I can recommend the following.

    1) El Naturalista. I have two pairs of winter boots from them that are fantastic, plus a couple of other styles – heels, sneakers, clogs etc. All but the clogs (obviously) have deep insoles that can be removed and are fantastic for orthotics. However, you do have to like chunky rubber soles. I think they look cool, but… (And for reference, I’ve never paid less than 100 euros for a pair.)

    2) Think! I believe the company is Austrian. One of the few brands that does heels with thick removable insoles – if you want something nice enough to wear with a dress, then it’s a good choice. Try to get the winter range – they have solid rubber soles, whereas the summer range has lighter, thinner soles that don’t last as long. They do fantastic loafers and ankle boots too. Once again, 100+ euros.

    Other: Semler can look a bit granny-like, but when they get it right, they’re great. I have a new pair of knee-high boots from them that are fantastic (and in addition to removable insoles come in four calf sizes!) Josef Seibel is often recommended to orthotic wearers, but they’re generally too narrow. Mephisto is good too, but has the same narrow-ness problem. (My feet aren’t that wide – my orthotics are.) Finn Comfort has the odd hit among the granny stock, but seem to be better for larger feet than mine.

    Campers are lovely, but they’re rarely deep enough for orthotics. (Believe me, I’ve tried.) Ecco has some very good shoes too, and are reliable. Pricier abroad than they really should be, though, and you need to shop in store – the depth of the insoles can vary quite dramatically. The Art Company does incredibly nice stuff, but it’s expensive and the styling is very distinctive – depends on your taste.

    Clarks are good, but you have to have the right feet. I’m just between two sizes, and nothing there ever works. In addition, they don’t have as many removable insoles as you’d think. Designed more for the sensible shoe buyer than the orthotic wearer, I think.

    Look for something made of fairly sturdy leather, given the description of your orthotics. (They sound just like mine.) Even in a well-fitting dress shoe, they’ll grind away at the side at the point where they arch up. (I have completely archless feet. Ouch.) Unless you buy something as wide as a boat, which then won’t fit properly elsewhere, this problem is hard to avoid in anything that’s not a winter boot or a sneaker. The shoes mentioned approvingly here will all survive at least two years though, despite this problem.

    Basically, the holy grail in this market is something stylish and affordable. Throwing money at the problem helps, but obviously only if you have it. I didn’t growing up, and used to burst into tears regularly whenever we went shoe shopping, because all the shoes that didn’t actively tear my feet to pieces that we could afford were unreletingly hideous. So the best of shopping luck!

  • Megan says:

    I am all about the Keens. Also, I may be the only human being alive who won’t recommend Danskos. Biggest waste of money of my life. I got them, sank money into them, because I had heard about how awesomely comfortable they are. To my feet, they are merely okay; Keen’s are much better for me.

    I got these:

    I have twisted my ankle in them more times than I can recall. I have completely fallen to the ground a couple times and cut the hell out of my shins. These are the only shoes I have this problem with.

    I only own a few pairs of shoes, and sometimes these are the only option. And I hate myself every time I wear them. NEVER AGAIN.

  • GJR says:

    I love this topic because I’ve also been struggling to find shoes to wear with orthotics, or shoes that have enough support that I don’t need the orthotics. I’ve been wearing Finn Comfort sandals at home and I just got some Ziera (formerly Kumfs) mary janes to wear at the office. The Ziera shoes have enough arch support that I don’t need to put my orthotics in them to wear around the office and out to lunch.
    For walking, though, I still have to wear sneakers with the orthotics.
    I’m now looking up a bunch of these suggestions because I do need some winter boots.
    The recommendations for going to a good old-fashioned shoe store are spot-on. You will spend more money at first but the sales people should be able to help you without a lot of shipping packages back and forth. I went to Eneslow in Manhattan and they special-ordered the Ziera’s in my size. I probably never would have noticed these brands in the sea of choices on Zappos.

  • Karen says:

    I second australienne on the el naturalista – crazy expensive ($200 cdn) but will give you years of daily wearing. I bought mine because I live on the West Coast of Canada, and I was tired of having my shoes act as sponges in the winter rains. The rubber sole and a regular coat of mink oil means I have lovely dry feet.

    Another good one is Joseph Siebel. I’ve had the pair I’m wearing right now for 3 years – worn every day (until I got the el naturalistas), still presentable, and have plantar fasciitis orthotics in them.

    That said, neither of these is super dressy. The el Nats will go with casual skirts, jeans, and not particularly fancy pants. But, if you go to an independent shoe store, you’ll find all sorts of quality shoes in different styles.

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