Pretty ugly*

There's an entire category of fashion that gets labeled different ways ('ironic,' 'clothing men don't like,' 'fashion victimy,' etc.) but that amounts to the same thing: clothing that's intentionally ugly, yet worn by women who want to look pretty. Think Chloe Sevigny. Think one-pieces with harem-pant bottoms. Think... think absolutely any garment, worn on a woman who clearly pays a good deal of attention to her appearance. If styled in a way that implies This Is Fashion, or put on a model (see: why "models off-duty" is a useless concept), it's all fair game. Unitards, high-waisted jeans with pleats, men's workshirts, flannel...

The latest installment: Jessica Grose, a Slate writer, discovered German orthopedic sandals, which she's been wearing "for years," and which can now, and I've seen it myself, be found in trendy shoe stores in the US.**

Here's where things get tricky. Grose writes: "I don't know about other Worishofer owners, but my love for them is earnest—I genuinely think they are attractive." And yet! For the "grandma sandals" look to work, the wearer cannot herself be of grandma age, just as for the "boyfriend" look to be that and not simply "butch," the wearer must (go out of her way to) give off the vibe of someone who'd have, well, a boyfriend. This is the difference between menswear-as-trend and crossdressing. And these are fine lines, so to speak. Grose may believe she genuinely likes these sandals, but she first noticed them on a stylish (and presumably sub-80) friend. Indeed, she refers to the shoe's "under-40" wearers. What happens at 40?

Because the effect is in the contrast - pretty-young-thing in outfit intended for someone far older - or far more masculine. It all hinges on the visible non-membership of the wearer in whatever category of person one imagines the garment or look to be for. Straightforwardly pretty (or chic, or sexy) clothes, meanwhile, are quite obviously intended to enhance the appearance of the wearer. The message sent by pretty-ugly clothing is that the wearer must be the following to pull that outfit off: 1) naturally beautiful, 2) unconcerned with how she's seen (aka not trying too hard), 3) you get the idea.

I'm torn. On the one hand, I support all trends that permit women to wear the hot new thing without cutting off circulation or stumbling into train tracks or what have you. On the other, I don't like this whole 'let's not look pretty, yet in doing so show off how pretty we really are' strain of fashion, either. All of this brings me back, boringly enough, to the straightforwardly this-looks-nice gamine look so easily procured in Paris, and so conducive to wearing flat shoes and otherwise comfortable attire. Breton stripes and narrow (not "skinny") jeans, ballet flats, feels a bit costumey when actually in France, but basically, problem solved.

*Not to be confused with "jolie laide," which is French for either, this young woman's ugly but has rich and famous parents so we have to say something nice, or, this woman's all-around attractive but has 'ethnic' features that prevent her from fitting the Bardot standard.

**A well-kept secret is that some of NY's best shopping is on residential and untrendy West 72nd Street. Those sandals included, although in that locale it's a fair bet they're being worn unironically for real.