These were my take-aways:
- If a skirt or dress requires special undergarments, it ain't gonna get worn.
I've got some of those no-show "hipster" undies from H&M that really aren't bad, compared to thongs, but still. The notion of a strapless bra will not even be entertained. This is a really good thing to know about yourself and keep in mind while shopping :-P
- Getting into or out of a tall car in a short skirt is exceedingly difficult.
I've got a lot of sympathy for Britney and Lindsay now. Though, knowing this information, I probably wouldn't go commando.
- You'll get more comments when you don't wear pants
Some of these will be the creepy-leering-dude sort, many will be the ladies-of-all-ages saying your outfit is cute sort. Nobody likes the first kind, and if you're as painfully introverted as I am you may find the second kind a little stressful too, even though they are delivered with the kindest intentions. I find that sunglasses really cut down on how many people talk to me, as does walking around with a gait and expression that says "I'm running late because of someone else's incompetence and they are definitely losing their job and at least one limb when I make it back to the office."
More like "Keep Calm and Don't Fucking Talk To Me"
- Tights need to be like, three inches longer in the leg.
Seriously, I'm not particularly tall and I don't usually have to buy "long" jeans, but tights crotches are almost always way too dang low. Makes you feel like a penguin, but not as cute.
- A skirt-based wardrobe is annoying to launder
All kinds of tights and fabrics that shouldn't go in the dryer... just how many lingerie bags is a gal expected to own, man? I guess you could choose only hardy-fabric items and skip the tights and it wouldn't be so bad, but...meh.
- I love jeans... but skirts are more fun to style.
They're also tougher to style, since you have to actually consider the colors on your bottom half instead of just going "PFfffff jeans go with everything!" I've got my wardrobe whittled down to a fairly limited palette, though, which definitely helps.
- I definitely feel more comfortable in skirts than when I started
...which was the goal (I'm prone to feeling too "dressy" and getting a bit self-conscious... it's also the reason I rarely wear earrings.) I'm also kind of sick of them, but I'm sure that'll fade. There were a few skirts/dresses I didn't get around to wearing, and now I need to take a long hard look at them and figure out if I really like them enough to keep.
All in all, definitely a challenge I'd recommend.... and it's not too late, I just saw the word "Frocktober" somewhere! And then there's always "No-pants November" and "Dresscember"...