The art of the casual skirt

Woody and Jessie

I wear skirts most of the time. Honestly, in the summer, I just like them better than shorts. I feel more modest, particularly considering how difficult it is to find shorts that aren’t reeeeealy short. I think shorts look bad with unshaved legs, but skirts look better. And they’re more fun. I wear skirts a lot in the winter, too, but it kind of depends on how my internal thermometer is doing. I hate being cold, and I get cold really easily usually, and some days I just can’t stomach of the thought of a skirt even with tights and legwarmers.

A few weeks ago, I was talking about skirts with a friend of mine, who mentioned that she thought my skirt even looked fine with the tennies I was wearing, and that she doesn’t wear skirts that often because she doesn’t think she can pull it off. This conversation got me thinking about casual skirts.

And it kind of is an art.

I have not always worn skirts. I formerly reserved skirts for special occasions, church, and sometimes work. When we started dancing, I started dressing vintage more and more, even for daily life, which of course meant skirts, but they were dressy skirts. Dressing vintage inevitably means dressing up – with stockings and fancy shoes. (No, it doesn’t have to, but fashion in the past was much more dressy, with casual shoes and styles reserved for the younger set or daywear for an at-home wife.)

But vintage for dancing is completely different. First, when I’m dressing vintage for dancing, I AM taking on the part of a younger person. Badass swing dancers in the 40s were not thirtysomething married women. They wore skirts (usually) and Keds-style tennies (image). (Wedge-heeled dress shoes were another popular choice – image.) Second, dressing for dancing means dressing to be comfortable. So, at least for dancing, I often wore skirts with Keds-style tennies. And I got accustomed to the idea of skirts + tennies.

I don’t really know what changed skirt wearing for me, though. I guess it was my mom wanting to buy me a skirt for my birthday a number of years ago. I couldn’t find anything I wanted to buy at Younkers, the only store that existed in her world (other than Draper’s and Damon’s). She finally, exasperated, asked what I DID want. Something in natural fibers (cotton, linen, hemp, etc) that I could wear with my one pair of non-dancing shoes – brown Keen clogs. We didn’t find anything. She offered to get me another pair of shoes. Not the point, mom!

The next week, I made myself a half-dozen linen and cotton skirts, each of which I could wear with my one pair of (insanely comfortable) shoes. And I haven’t looked back since then.

I think the key to wearing skirts on a daily – or at least regular – basis is twofold: the right skirt and the right shoes.

1. The right skirt. You have to get away from the Dressy Skirt mindset. Ann Taylor? No. This? Yes. Your definition of “casual” may differ from mine, but I tend to think of slightly longer (knee or longer), less structured (no pleats, tucks, tailoring), natural fibers, and fun prints. If you look at it and think you’d need to wear pantyhose, it’s not casual. If you look at it and could pair it with a T-shirt, it’ll work.

2. The right shoes. I personally think that skirts and running shoes look kind of tacky, unless you’re on your way to work, or on your lunch break. (Exceptions also given to occasions when you’re going to be doing a lot of walking, like wearing a skirt with tennies at the Fair, DisneyLand, an all-day expo, etc.) YMMV. One of the reasons I love my Keen clogs so much is that they look great with skirts – in my opinion. Again, YMMV. Sneakers (like Converse), leather slip-ons, etc. tend to look decent with skirts while still being comfortable enough for daily wear.


One response to “The art of the casual skirt

  1. I love skirts! I have a huge pile of them that I plan to wear as soon as my hips figure out that I’m not still pregnant. I should sew myself some skirts, but since I’ve never sewn anything for myself it would take way more brain power than I have right now.

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