I think Dapper Day is usually just that one day, but I love dressing up to go to the parks, and I've never really worried about looking silly, (I mean, tons of people are walking around with mouse ears on their heads and that's pretty silly, too!) It's true that a lot of people just wear jeans, t-shirts, and sneakers because they're comfortable, but I think it's sometimes more fun to look nice--you can do it comfortably, too. In my opinion a cute dress or skirt with tights and flats or even nice wedge heels feels more comfortable. - Spoonful_O_Sugar  436.2 #285 10:55AM

First off, who cares if you're the only ones dressed up? As long as you're having fun, then you don't need to worry. Second, I've seen people dressed up the whole weekend and third, check out the search feature for more on Dapper Day. - DisneyFanZoe  1096.7 #75 10:44AM

I say dress up that day or the whole weekend. Whatever would make it more fun for you 😊👍 - Sweet_Irish_Cream  2554.7 #22 10:46AM

I'm going to miss it again. =( at least I went to one of the first one where I met a lot of awesome MWers. - VfxGenie  1353.5 #59 11:29AM

I know people will be in the parks for the whole weekend because of room discounts. Since BVS opened, people dress up all the time. However, "spring" Dapper Day is actually on 2/24/13, a Sunday. - Jacqueline  546.7 #205 11:39AM

I wanted to try this...this year. I hope I get to - DumboGal70  86.0 #3193 11:44AM

Thanks everyone for your input :) I think we're gonna go ahead and dress up on Saturday. We get to go shopping for outfits this weekend :) - MrsDisneyMommy29  264.1 #880 6:30PM

It's usually just that specific day but if you wanna dress up all weekend, why not?! :) - sarahpie  275.3 #775 6:38PM