What I Learned from Wearing Dresses Every Day for a Month

December 31 marked the end of the year, but also the end of Dressember, in which I –– and a whole bunch of other people –– pledged to spend the month of December wearing dresses every day. 

As challenges go, it actually wasn’t a particularly difficult one for me, not only because I wear dresses a lot anyway, but because I spent part of the month in a completely different climate. That meant I had access to my summer dresses as well as my winter ones, and it also gave me a great excuse to get dressed up every night for dinner, thus allowing me to wear the occasional pair of shorts during the daytime: a little bit cheaty, but hey, I was on vacation!

And how did it go? Well, I wore a dress on every day but one: the single exception was the day we flew home from Tenerife, and as it was a full day of travel, which happened during The Great Airport Shutdown of 2010, I decided to give the dresses a miss and went for the warmest, most non-crease option I could find in my holiday wardrobe, just in case we ended up being stuck at the airport for the rest of our lives or something. I DID, however, wear more than one dress on a couple of the other days of my vacation (not at the same time, obviously: I mean one during the day and then a different one in the evening), so hopefully that balances out my one dress-free day and makes everything right with the dress-wearing world once more.

HERE’S WHAT I LEARNED FROM MY MONTH OF WEARING DRESSES EVERY DAY…

1.
Dresses aren’t any harder, or any more complicated to wear, than jeans or sweatpants

When I told people I was going to try wearing dresses every day, the most common reaction was something along the lines of “Oh, I just couldn’t be bothered with that!” or “I’m too lazy to get dressed up every day!” as if the act of throwing on a dress is some gargantuan task, involving several hours of manpower and a tremendous amount of forward planning. Here’s the thing, though: it just isn’t. We don’t live in the 18th century any more. Putting on a dress doesn’t involve lacing yourself into a corset, or calling in the maid to help you struggle into fifteen crinolines.

In fact, I can throw on a dress and a pair of shoes in the same amount of time it takes Terry to put on his jeans and t-shirt: sometimes I can do it faster. It isn’t any more complicated than jeans, either: in fact, given that some of the time you only need to find one other item to wear with the dress (shoes or boots) as opposed to at least two (shoes, top), you could argue that the dress is actually the easier option, and I have argued this point many times, particularly in the summer, when it seems to me that a loose cotton dress and a pair of sandals is easier and more comfortable to wear (as well as being quicker to put on) than some other combo of top + bottoms. I also think dresses can be more practical at this time of year, too: no trailing hems to drag through the snow and rain, no restrictive waistbands to loosen after Christmas dinner: what’s so complicated about that?

2.
Just because you’re wearing a dress, it doesn’t mean you’re “dressed up”

This is a more complicated objection to work around, because, as I’ve noted before, society in general (or perhaps just where I am, who knows) seems to feel that wearing a dress – ANY dress – means that you’re “all dressed up, OMG!” And this wouldn’t matter, really, except that for reasons that aren’t particularly clear to me, being “dressed up” has become something that’s very much frowned upon. Maybe it’s because it’s considered frivolous, maybe it just makes other people feel like THEY should be “dressed up” too, I don’t know.

But despite everything I’ve said about dresses being comfortable, quick and practical in many situations, if you choose to wear one you WILL endure questioning about why you’re “so dressed up!”, and it WILL sometimes be the kind of questioning that’s designed to make you feel uncomfortable, as if you’ve just been caught doing something BAD. You will also be stared at: when we were on holiday, Terry and I actually made a game out of counting the people who’d stop what they were doing to blatantly stare at me as if they’d never seen someone wearing a dress before, and this was a totally new concept to them. Let’s just say it happened a LOT. In fact, if I didn’t get at least a few blatant stares on the way down to dinner each night, I’d start to wonder if maybe I should go back and change…

3.
People will get used to you wearing dresses every day

All of that said, if you’re prepared to stick it out and break through the “OMG U R WEARING A DRESS!” barrier, you’ll find that people will get used it to pretty quickly. Maybe not the people who visit a certain hotel in Tenerife in the winter, mind you. They’ll never get used to it. (Other things They will never get used to: keeping the volume of Their TVs at a volume low enough for it not to be audible ten miles away; the idea that loudly blowing your nose at the dinner table, foghorn style, and then inspecting the contents of your handkerchief, is NOT ON) But the people who know you in real life will very quickly come to realise that you wear dresses because you like them, not because you have a job interview, are an airhead or secretly wish you were Marie Antoinette (which would be silly, because she got her head chopped off, and you all know how I feel about THAT…), and will say no more about it. This will be a happy, happy time.

4.
YOU will get used to wearing dresses every day…

As the end of Dressember drew near, and I started to contemplate the prospect of having access to my entire closet again, I realised that I hadn’t really missed the jeans and trousers. I missed the skirts, sure, but as skirts aren’t so very different from dresses (and were actually permitted under the Dressember rules), I’m not sure that counts. I won’t be spending January in jeans: in fact, I’ve worn dresses every day since the challenge ended, and it’s no longer a novelty, either to me, or to anyone who knows me: it’s just how I dress, with no explanation necessary.

Isn’t that refreshing?