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.
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.
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.)
And I’m okay with that.