Can you help an incredibly picky person find shoes?
August 9, 2017 3:10 PM   Subscribe

I'm looking for casual women's shoes. Difficulty: big, severely flat feet, and Chicago winters. What looks good and doesn't hurt these days?

I'm a woman in my early 30s, in a technical role, but not working for a software company. My daily wear is typically jeans and a plain t-shirt. In the winter you can throw in a hoodie or sweatshirt of some sort too.

What I currently wear:
- For the past 15 years my daily shoes have been converse. They used to be amazing, but I usually end up walking 4-5 hours a day, and the converse are killing my feet after 2 hours.
- My business casual shoes are Sperry's. I prefer the type with the shorter... nose? like this one has. The longer type like this just look silly on me. However, I can't wear Sperry's often because my over-pronation tends to make them wear them out faster.
- For formal wear I pretty much just try on shoes, get frustrated that none of them account well for how wide my feet are, buy a cheap pair of flats, and then throw them away after the event. I don't do formal events much anyway.
- Nike Lunarglide 7s for exercising.
- Barefoot as often as possible.

- I over-pronate. Horribly. For example, if I'm wearing flip flops or sandals, when I take a step, the inner part of my foot will start completely on the flip flop. By the time my foot reaches the ground again, about 20% of my foot near the arch will be hanging off the flip flop. It means I can't wear things with open sides, or things without structurally sound sides (I've been wearing out the sides of my Converse faster in recent years).
- I'd like something that can handle the less-snowy days of Chicago winters. Most normal athletic shoes can do this, but converse let my feet get cold way too fast.
- Unless there is a compelling argument, I don't want a running shoe. I work with a lot of business people in suits. While I can get away with dressing down, running shoes just feel out of place.
- Nothing with a heel. Not even a small one.

Shoes I don't like:
- Slip-ons like Toms. They make my feet look big.
- Adidas Superstars. I thought they were my new shoes, and then they stretched out. I also found them a lot heavier and clunkier than I was expecting.
- Clunky shoes like this or this.

What I like:
- Converse, minus the pain.
- I don't know. My converse are the only thing I've found that fit the roll. Hence the question.

What shoes should I be trying on?
posted by Krop Tor to Shopping (17 answers total) 9 users marked this as a favorite
So, my biggest recommendation is good insoles, possibly custom insoles. I am a major over-pronator, and they're the only thing that allows me to keep a pair of shoes for longer than 6 months (otherwise one side wears down to the point of nothing and they become incredibly uncomfortable). A good independent shoe store will be able to help you find a good pair.

Some shoes that have worked for me:
Teva boots. They make a bunch of different styles, but I particularly like their low boots like these ones because they work well with both jeans and skirts. Note: these look like they have a small heel, but because of the way the sole is designed, your foot ends up totally flat -- I also cannot stand even slight heels and these do not bother me.
These flats. They are some of the only flats I can wear all day without murdering all those around me. Even without tights!
These Hush Puppies. Again, just super comfy, looks good with slacks.
posted by rainbowbrite at 4:00 PM on August 9, 2017 [5 favorites]

I'm kind of a broken record on Keens, but it's for good reason! I need to wear NO HEEL, and I have wide feet, and I am amazed everytime I put on my Keens. They just fit so well.

I have a pair similar to these. They give you the Converse-like look, but with better support and more comfort.

I also have a pair of Keen's Mary Janes's which I love, but the ones on their website right now all have a pretty long nose, so they might not be for you (and/or too chunky).
posted by hydra77 at 4:49 PM on August 9, 2017 [3 favorites]

Have you tried the Converse One Stars or Jack Purcells? The One Stars are suede and warmer than the canvas Chucks.

Some of the New Balance Classics are cute and can look like a fashion choice like Chucks.

Some brands to look at would be Ecco, Clarks, Vionic, Mephisto, Rockport Cobb Hill.
posted by Squeak Attack at 4:56 PM on August 9, 2017 [1 favorite]

Consider boots/booties in wide widths. Some brands that are as comfortable as sneakers: Munro, Earth, Cobb Hill.

I agree you might get the look of a slight heel on some styles, but I urge you to try some anyway because they make a flat surface for your foot-- I only wear comfortable, stable, can-walk-for-hours shoes for my wide, Converse-happy feet, and many of my boots have a heel like the Keens rainbowbrite links above.

Bonus: plainer styles Look great with jeans or dresses.
posted by kapers at 5:01 PM on August 9, 2017

I'd try some sort of leather driving moc. Or maybe Merrell boots.
posted by sulaine at 5:53 PM on August 9, 2017

Barking Dog Shoes is an amazing blog for people with foot problems and hard to fit feet.

Here are some posts for wide feet. Maybe something like this oxford or one of these casual lace-ups?
posted by hydropsyche at 6:13 PM on August 9, 2017 [1 favorite]

I too love converse. Have you tried some of the newer styles with the Nike lunarlon running shoe insoles. (Nike bought converse a while back). These have waterproofing / weather shield and the running shoe insoles. I've found that the shoes with the better support run a half size or so smaller than regular converse. I also have a pair of rubber coated converse lined in fleece/felt that almost get too warm in winter.
posted by DarthDuckie at 6:25 PM on August 9, 2017 [1 favorite]

Dansko makes non-clogs that I find amazingly comfortable. I have their sneakers, along with their oxfords and flats that I wear for teaching. But I find Sperrys excruciating to wear, so your feet may be different.
posted by Peach at 7:37 PM on August 9, 2017

Nthing Earth and Cobb Hill. With the caveat that I have tried on multiple pairs of Cobb Hill shoes, and they are so comfortable on my wide, flat, big feet that I want to cry - BUT I have not bought any because I don't like their styles and I think the "noses" on most are too long. So you may feel the same. But wow are they comfortable. Earth are similarly comfy.

I also have a pair of Eurosoft ballet-style flats that are great. Great support but low-key flat profile.
posted by lunasol at 8:55 PM on August 9, 2017

My problem feet are different enough from your problem feet that I can't make specific shoe recs, but I second hydropsyche's rec of the Barking Dog Shoes blog.

I think the term you're looking for is "low vamp" shoes [what you're calling "short nose"]. It means that the shoe upper terminates fairly low on your foot. For example, ballet flats have a low vamp, while oxfords have a high vamp. [Not that I'm suggesting ballet flats for you, as they have very little support.]
posted by Pandora Kouti at 9:20 PM on August 9, 2017

You might take a look at Cole Haan's extended widths selection. I have a pair of their loafers that are both structured and extremely comfortable (I walked ten miles in them yesterday), and look great with jeans. Similar in style to the Sperry's, but a bit more supportive and dressier.

I'd also definitely look into insoles if you haven't already--and do so at a serious "comfort shoe" store, where they should have multiple options that you can try on, as well as a lot of the shoes mentioned here.
posted by dizziest at 2:12 AM on August 10, 2017

I have profoundly flat feet and pronate severely, so much so that I really cannot walk barefoot. Strong second for you to move to insoles. In fact, I think you should visit a podiatrist and get custom orthotics--this has been a lifesaver for me and will probably help you a lot as well. Also some physical therapy to learn how this impacts the rest of your drive train and exercises that will help compensate. I just did this for the first time at 47, after 20 years of orthotics and bad gait, and bitterly regret not having done it sooner.

Re: shoes: if you have orthotics, you'll need to find shoes that can accommodate them. Many styles have removable insoles so orthotics can fit. is a retailer that specializes in footwear for tricky feet and they have an 'orthotic friendly' category. Zappos does too, I believe.

For footwear that can't accommodate orthotics, I find that Vionic makes excellent supportive flip flops, Birkenstock makes excellent supportive sandals, Haflinger makes excellent supportive slippers.
posted by Sublimity at 4:04 AM on August 10, 2017 [1 favorite]

My orthopedist recommends the Superfeet insoles as being as good as custom, and a fraction of the cost and bother. I'd go to a comfort shoe store that sells them, get a rec for the best one for your feet, and try those in your Converse.
posted by fingersandtoes at 6:15 AM on August 10, 2017 [2 favorites]

When is the last time that you bought Converse? They recently came out with a redesign that is supposedly more supportive.
posted by serelliya at 11:00 AM on August 10, 2017

Yeah, you might want to try the new comfort Converse styles branded as Chuck Taylor II. They cost more. In the overhead photos online the lurid lime-green insole is visible.
posted by Scram at 7:58 AM on August 11, 2017

If you like being barefoot, I suggest trying the Vivo barefoot brand. I had great luck with it until I got tendonitis and now being barefoot leads to pain. Now I am getting Birkenstock shoes (yes, shoes, not sandals, they significantly expanded their offerings), which I had liked before but now are the only reliably comfortable brand for me. I also have flat feet, and wear out the outsides of my soles faster than the insides.
posted by Salamandrous at 6:39 AM on August 12, 2017

This site might help you find suitable athletic shoes
posted by infortunity at 8:45 AM on August 26, 2017

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