Fashion Friday: Dressy Comfortable Shoes, and Thinking Outside the Box

So I recently solved a fashion conundrum that’s been seriously bugging me for some time. I solved it by having to radically re-think what I’d consider to be an acceptable solution. I had to let go of some preconceptions; I had to think outside the box. And I thought I’d share with the rest of the class.

For months — years, actually — I’ve been on a quest for shoes that are both dressy and comfortable. I had high standards in both departments: I needed the shoes to be dressy enough to look good with dresses and skirts in a professional setting… and I needed them to be comfortable enough to walk in for miles, comfortable enough that I could be on my feet all day in them. And this being me, I was picky about how they looked. I wanted them to be comfortable — but I didn’t want them to look frumpy or boring. I wanted them to be stylish and expressive and interesting.

Ballerina flats
Before you chime in: Do not tell me about ballerina flats. Ballerina flats have been nothing but a bitter disappointment. I must have weird feet or something: I have bought more pairs of ballerina flats than I care to remember, and not one of them has given me more than three days of wear before I gave up in disgust. (And yes, I’ve gotten good-quality ballerina flats from good manufacturers.) They don’t give me enough support — I have mildly crappy feet, and need a certain amount of support — and after wearing them for more than an hour, my feet ache like crazy. And they chew up the backs of my ankles into the bargain. My four-inch stilettos are more comfortable.

I’ve spent more time than was probably necessary pondering this conundrum, and trying to figure out why it was so hard to solve. I think the basic problem is this: In the current language of women’s shoe fashion, “dressy” tends to mean “high-heeled.” And “dressy” combined with “stylish” strongly tends to mean “high-heeled.” You can find low-heeled or flat shoes that are stylish — but they tend to be fairly sporty or casual. You can find low-heeled or flat shoes that are dressy — but they tend to be fairly plain. In the same way that it’s hard to find clothing to express “sexy woman over fifty” because our culture considers the concept “sexy woman over fifty” to be nonsense, it’s hard to find dressy, stylish flat shoes for women… because in the language of fashion, the very concept is something of a contradiction.

On a day-to-day basis, my usual answer to this conundrum has been boots. About which I have already waxed poetic. But boots have a certain sporty, rakish vibe, and in many situations they’re just not right. They’re not dressy enough for many professional settings; they’re often not dressy enough for evening. And they’re definitely not okay when it’s stinking hot.

So I’ve been searching, and searching, and searching. Every time I went into a shoe store, I kept an eye out for dressy, comfortable shoes that didn’t make me feel like I’d taken a sleeping pill. Every time I looked, I was disappointed.

Pilgrims by John Fluevog
And then I came across these.

And I found myself having to think outside the box.

I freaking love these shoes. I fell in love with them pretty much at first sight. But before I could commit, I had to seriously re-think what I was willing to consider an acceptable solution to my little conundrum.

The shoes are enormously comfortable. John Fluevog knows what he’s doing: the heels I have from him are easily the most comfortable heels I own, and these new babies are almost like sneakers. And they’re definitely stylish. Again — John Fluevog knows what he’s doing.

But they’re also very quirky. They’re stylish and expressive, but they’re not conventionally pretty. They’re more than a little bit nerdy, and way more than a little old-fashioned. The very name of the shoe is “Pilgrim” — not exactly the apotheosis of feminine grace and sophistication. They carry strong overtones of “Wicked Witch of the West.”

And I realized: Maybe that’s exactly what I needed to break this conundrum.

Maybe, if I want dressy, stylish, comfortable women’s shoes, I need to re-define what I mean by “stylish.” Maybe I need to let go of “conventionally pretty.” Maybe I need to let go of conventional femininity. Maybe I need to let myself be a little old-fashioned. Maybe I need to let my stylishness be quirky, nerdy, witchy.

(I also maybe need to spend somewhat more than I normally do on shoes. That’s something Ingrid kept reminding me of when I was griping about my conundrum: more-expensive, higher-quality shoes tend to be more comfortable, and longer-lasting, as well as prettier. But when I think of how many pairs of useless ballerina flats I’ve bought in my life — and the amount of money I’ve wasted on them — the math on this totally adds up.)

Pilgrims by John Fluevog
If I’m going to reject the notion that women have to wear heels if we’re going to be dressy and snazzy — and I do reject it, I love my heels but I hate the pressure to wear them — then that’s an unconventional stance. It’s a quirky stance. It’s a stance that rejects conventional notions of beauty and femininity. It’s a stance that embraces the fundamental concepts of beauty and femininity, and rejects the notion that women have to cripple ourselves to participate in them. It’s a stance that reclaims female nerdiness, and demands that it be seen as professional and urbane and creative. It’s a stance that thinks the Wicked Witch of the West got a bad rap.

And I’m okay with that.

Fashion Friday: Dressy Comfortable Shoes, and Thinking Outside the Box

39 thoughts on “Fashion Friday: Dressy Comfortable Shoes, and Thinking Outside the Box

  1. 1

    Well, they look like they would kill my feet within 5 minutes, but they do look good.
    But seriously, whenever shoe-fashion decides that those very pointy shoes are in, I despair and take a look at the men’s section because I just. can’t. wear. them.
    My feet are wide. My grandpa used to call them “Päädchesträter”, path-treader, meaning feet so broad that they would make an ideal path between the different sections of the vegetable garden.
    Really, shoes are another one of those areas where fashion decides how your body has to be and if it isn’t you’re handed a big scarlet letter. Look at those shoes.

  2. 2

    Oh, that’s just cruel… I’d never heard of John Fluevog, and now, lured by those awesome (although possibly too pointy) shoes, I have spent several minutes browsing his website and *wanting* *moar* *shoes*. I live in trainers. I cannot have these shoes. But my goodness, if I needed smart, covetable, comfortable shoes for work, I’d be doing my very best to buy them.

  3. 3

    Fluevogs rule! Another brand that makes comfy but funky shoes is Fly London – lots of cute boots as well as dressy shoes. I’m in a line of work that takes me to trade show/market events regularly and I can’t do conventional heels anymore. I used to have shoes I’d call my ibuprofen shoes (pop a spin killer before you even put them on), but I’ve found that I function better and am much happier with my more expensive but much more comfortable Flys and Fluevogs. Miz Mooz is also a great brand.

    My 15 yr old daughter bought her first pair of “serious” shoes this summer, a pair of Fluevogs very much like your picture. She needed dressy black shoes for the orchestra she plays in. She even paid for them herself. Smart kid!

  4. 5

    love those shoes. I have absurdly high arches so I so rarely can wear nice shoes. I lust after the ones that Nadia G wears on her cooking show. Alas most of the time I’m wearing Clarks Unstructured, probably the most damn ugly shoes on the planet. But they are comfy.

  5. 9

    As someone who has recently seen Wicked, the Wicked Witch rocks. Elphaba is by far the coolest character in the show, and I can see nothing at all wrong with emulating her style.

    Personally, I have flat, long, narrow feet, so finding shoes that fit me at all is always a pain, let alone ones that look good.

  6. 11

    Shoes! I love shoes! I read Isis way longer than I normally would have because of her shoe posts. (The apparent hypocrisy between her feminism and her total silence on the misogyny and sexual abuse perpetratedy by the Catholic church finally wore me down).

    My issue is that I ride the bus to work, so I need shoes I can slip on and do my orc-jog for several blocks to catch the bus. I don’t want to switch from sneakers to real shoes, and besides, I usually cut it so close that I literally don’t have the time to tie a pair of shoelaces if I want to catch the bus. I’ve found kitten heels to be a good solution. Also wedges. Also Western boots. I have way too many shoes – how can you have too many red patent leather kitten heels?

    Giliell: I have wide, spatulate feet (some would say hobbit feet w/out the fur). The trick with pointy toed shoes is that the point extends past your toes. They are great with wide legged pants for extending the line of your legs (yes, I am short, and yes, I watch What Not To Wear religiously.) I do have some very pointy-toed shoes that are so long that they catch on the carpet at work… but they’re so cute!

    Fluevogs are way out of my budget (I haz a sad).

    A similar look is short Western boots. Shoe height, not ankle height. I have a couple of those.

  7. 12

    Great find!

    And I can totally sympathise with the ballerina flats issue. I have no idea what kind of feet they’re supposed to fit, but for me they combine all the bad aspects a shoe can have: Constricting the toes, rubbing at the back, and somehow just wrong the mechanics of walking.

    The only really flat but dressy shoes I ever managed to find is a pair of light brown brogues — not quite as comfortable as sneakers for really long walks, but still pretty good, and very nice with a skirt as well as with jeans.

  8. 13

    Yay, you!
    A good friend of mine is a huge Fluevog fan. I had a feeling that would be your solution when I started reading this very cool post. Then I saw the photo and said…hmmm, those look like Fluevogs. Then I read the accompanying paragraph.

    Anyway, thanks for sharing your solution. I hope you put many, many happy, comfortable miles on your new kicks.

  9. 15

    Love Fluevogs…and can’t wear them, because my insanely long feet are too narrow. I too search for shoes I can wear without them looking like orthopedic shoes. I wear Tom’s a lot, their original shoes let me walk for days, but wow are they ever not dressy, or office appropriate, or even remotely grown up.

    Happily, if this is my worst problem, I’m fantastically lucky!

  10. 16

    Greta, I really sympathize with you. I have a similar problem, but since I am retired now, and don’t have to dress up much, I usually wear black SAS sneakers and pants. I have wider-than-usual feet, and have a very hard time finding anything that fits and is comfortable, let alone anything that is stylish at all. I have a pair of flats that are comfortable and OK-looking. They just don’t look all that great with skirts. I, too, think I need to redefine what I really feel is “stylish”. At my age (senior citizen), and on my budget, I really can’t afford to worry about “style”. BTW, my SAS sneakers are VERY comfortable. And they are very high-quality — they LAST! — and are very worth re-soling. They were not cheap: $140!! — and that was a few years ago. (I now see that what I had thought was really expensive is really on the low side of expensive — yikes!)
    P.S.: I can’t wear pointy-toe shoes — hope yours turn out to be very comfortable in the long run.

  11. 17

    I have a similar problem Greta. Ridiculously high arches and insteps, plus wide feet (I’d never be able to wear the Fluevogs). Ballerina flats don’t work at all. I compromised with a pair of boots (winter) and nice sandals (summer). However, I *love* Oxfords and I’ve seen some with pony heels. If I could find a decent, affordable pair I’d be golden.

    Thankfully being academic no one really expects me to dress up and I can just be quirky.

  12. 18

    Fluevogs… I have three pairs.
    Black and red Bacalls; some cherry-red Angel Gibsons and from last year, a pair of silver Baroques.
    Speaking as a ballroom dancer, shoes should be high quality to help keep you dancing. I also recommend Ziera.

  13. 19

    I love love LURVE this shoe! Are those buckles? Good, lord, those are buckles. My problem is that I have awful feet and I adore a pretty shoe. These make me squee hardcore.

  14. 20

    “Style blogger falls in love with Fluevogs.”

    Aloit the media!! 😉 yep, Johnny F knows his stuff. i’m surprised to read that this shoe is ‘out of the box’ for you – i’ve worn/coveted similar funky styles of shoe since i was in high school (i’m just 6 months younger than you). I am happy for you that your horizons on what’s fun/stylish to wear are spreading! On top of the oppressiveness of the standard femme stereotypes, it’s just plain boring when everyone tries to look the same.

    vive la difference!!! 🙂 steph

    p.s. hopefully we’ll run into each other at the Johnny F. store someday!

  15. 22


    The trick with pointy toed shoes is that the point extends past your toes.

    Unfortunately, those feet are also very long.
    I tried them. In my size (if I can get my foot into them), my shoes arrive like 10 min. before I do 😉

  16. 23

    Those are wicked shoes, Greta! Love ’em and I’m happy you found comfortable wicked shoes* , have a long lasting, versatile addition to your wardrobe and got something special just for you after all you’ve been through lately.

    *Difficult for me, ’cause I’m a size 6 wide. Finding comfortable and fashionable is a pain in the arse.

  17. 26

    Bob Seger:

    I’m going to bet that *nobody* who contributed to Greta’s recent appeal begrudges her buying some shoes. I’m going further out on that limb and betting that all the donors are *delighted* that she bought herself something that gives her pleasure and makes her life a bit easier.

    What would you prefer?

  18. rq

    I like the Wicked Witch of the West angle. Awesome shoes! I hope they live up to all expectations.
    As another wide-foot (peasant feet, my mother called them, for treading mud in the fields without sinking), I understand the annoyance of finding the right shoe in both width and length, not to mention style. My dream shoe is still out there, somewhere, but one day, one day…

    PS I also hate ballerina flats.

  19. 33

    “I was griping about my conundrum: more-expensive, higher-quality shoes tend to be more comfortable, and longer-lasting, as well as prettier. But when I think of how many pairs of useless ballerina flats I’ve bought in my life — and the amount of money I’ve wasted on them — the math on this totally adds up.”

    Instead of cost per pair, think of it as cost per year … one pair of high quality shoes usually outlasts several pairs of Famous Footwear’s $29.99 models. Then you have them resoled and wear them some more.

    And if they are outside the current fashion “box”, you can wear them for years. I wore a ludicrously expensive pair of Fry boots for over 15 years, through three sets of half-soles and many heel wear plates. Cost per year worked out to about $20, plus maintenance.

  20. 35

    (I also maybe need to spend somewhat more than I normally do on shoes. That’s something Ingrid kept reminding me of when I was griping about my conundrum: more-expensive, higher-quality shoes tend to be more comfortable, and longer-lasting, as well as prettier. But when I think of how many pairs of useless ballerina flats I’ve bought in my life — and the amount of money I’ve wasted on them — the math on this totally adds up.)

    Terry Pratchett wrote a similar sentiment in one of the Discworld books–Sam Vimes ruminates that one difference between rich and poor (and, I’d argue, between middle-class and poor) is that those with more money can afford to live more cheaply in the long run–and he uses the price of a pair of boots as the primary example–Sam’s $10 cut-rate boots give out after a season or two; a $50 pair lasts for a few years, paying for itself in the long run.

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