secret style envy & the search for cute, comfortable shoes

caro issa lk bennett

|  Caro Issa for LK Bennett…aka, the ones that got away (image via Natacha Steven)  |

We all have one, don’t we? That style we secretly admire over and over again out in the world and wish we could wear, but for whatever reason, we’ve absolutely-positively-100% ruled out. Maybe it’s skinny jeans, or mini skirts, or floppy hats or spaghetti straps. For me, it’s a great pair of heels.

Now, a lot of women get heels wrong. Horribly wrong. They clop through a parking lot in pumps that are clearly too big, too tight or too high, wincing and flailing their bodies about in a way that is, well, decidedly un-stylish. And yet. When they’re done right? The air of confidence, authority and – yep – sex appeal they immediately convey…it’s undeniable. Also, they’re so preeeettttyyy. The shoe department at Neiman Marcus is like visiting my favorite museum. Those gorgeous colors, the luxuriously soft leather, a contrast heel here, a light smattering of beads or intricate embroidery there…everything is so sculptural, so ornate, so available for purchase. Truly, I think 75% of the reason I watched Sex and the City was to see Carrie strut so effortlessly through the streets of Manhattan in pair after pair of jaw-dropping $500 heels.

Yes, whenever I clap eyes on a gorgeous pair of 4″ Manolos (don’t click…I’m warning you…), I get positively weak in the knees….and the hips and the ankles too. For no matter how much I adore them, no matter how much I want to strut through Union Square in a sky-high stacked heel sandal or a bejeweled stiletto, my newly arthritic body rebels (ah, this autoimmune nonsense just keeps giving and giving). My joints these days are an aberration, much better suited to high tops than high heels. Even wearing ballet flats is a treat for me now, and I’ve lately found myself veering toward that dark, spooky corner of the shoe department typically reserved for grandmothers and the stylistically oblivious.

This very week, in fact, while I should be celebrating the advent of spring the way God intended – by binging on Easter candy – instead, I’ve been torturing myself with a little sandal shopping. Where in years past, I’ve been willing to throw on the cutest thin, flat sandal I can find, this year, things are different. The joints are worse. And though I’m loathe to admit it, I find myself combing through page after page of, cough, “comfort” shoes. Let me just say, friends – it’s a bleak business. In my next life, I’m coming back as a shoe designer, and so help me, I’m going to design shoes with soles and arch support that don’t make me look like your Great Aunt Ethel, freshly rejected from a Portlandia casting call.

At present, there are a hilarious number of shoes headed my way for audition purposes – oh, my poor UPS man. While I haven’t made my way through them all yet, I thought I’d share a few of the styles that…well, at least came as close as possible to chic, without resorting to Birkenstocks (well, okay…one pair…).

But in the meantime, friends: what’s your secret style envy? Come on…I know you have one.

|   COMFORTABLE SPRING SANDALS THAT AREN’T (TOO) UGLY   |

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6 comments on “secret style envy & the search for cute, comfortable shoes

  1. Vanessa Gabor

    Following this closely. Heels are my style envy as well. Living in the burbs I can still tolerate out to dinner shoes, because they require no walking.

    On a recent visit to DC I was faced with entire days of walking..and wanting to look somewhat stylish. I followed your recommendation and purchased the insoles, smart wool no shows and New Balance..I was comfortable on my feet every day..Thanks!!

  2. Roxanna

    My Secret Style Envy: long, thick, glossy hair that (sigh) i will never have. Throw on a $5 Old Navy t-shirt, and that hair will make it look fabulous My corkscrew curls just don’t have the same effect, sadly…

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