Today after work, I went date shopping. The funny (read: pointless) thing about buying a new outfit for a date with someone you've never met is that all of your clothes and outfits are new to your date, so really you can just wear anything.
Today's shopping started with a trip to Nordstrom to buy a bra. Not because my date's going to get lucky or anything, but because I really just needed a new bra. From Nordstrom, I went to Gap because I had actually already chosen my outfit online before making the trip to buy it. The shopping trip was going to be expensive (bra=$60, pants=$50, shirt=$40) but worth it because not only was the outfit going to be good for the date, it was going to be good for work.
I carefully chose a nice pair of white summer pants and a striped blue shirt, but when I got to the store, I found out they didn't have the pants in my size. Neither did any other Gaps in town. They had the shirt, but I wasn't going to buy the shirt if I couldn't have the pants.
I set out to find another pair of white pants and I swear to you, I visited almost every store in existence. The whole experience was ridiculous and absolutely fruitless. Do you want the list of stores I visited?
White House | Black Market
Of course, many of these stores had white pants, but none that fit me like the Gap's white pants would have fit me (also, the pants are no longer available online in my size either, so I can't even buy them online and wear them on another occasion). It's sad that ultimately, Target actually had great white pants (and I had a gift card to Target) but they were also sold out of my size.
In the end, the shopping trip ended up being a lot cheaper than I expected, but I feel that I've at least invested some good time into this date. You see, date dressing is difficult---especially if it's someone you're meeting for the very first time.
First of all, I'm sorry to say, but you have no guarantee that it's even worth the investment. If you're just meeting the person for the first time, chances are fairly good that you'll get together, enjoy a good meal, and ultimately decide that you didn't really click. It's best when this feeling is mutual. It's better when you mutually feel that you did click. But let's be honest---that doesn't happen very often in encounters such as this.
Second of all, you have to dress nicely in a planned outfit, but you have to dress carefully. You don't want to overdress for the event and make your date feel like a schmuck. You don't want to underdress for the event and feel like a schmuck. You also don't want to dress like the girl you're doubling with. (Nat has informed me that she'll be wearing a blue shirt, jeans, and red shoes. I warned her that there's a fair chance that I, too, will be wearing red shoes.) Currently, I have overdressing and underdressing ideas.
Overdressing: I like a bunch of skirts that I have right now. I like a bunch of button-up shirts that I have right now. However, I would comfortably wear any of these outfits to church, and I don't want to go on a date in a church outfit.
Underdressing: I like my most recent Threadless purchases, most specifically my Lions Are Smarter Than I Am t-shirt. But I figure if I wear that, it may as well be an I Don't Give A Damn About You t-shirt. Of course, if I really wanted to send the "I don't give a damn" message, I would wear the Bob Saget t-shirt that Redras made for me, letting him know that Bob Saget is the only man who does it for me.
Unless I get some flashes of retail inspiration tomorrow and find a new outfit to buy, I'll probably end up wearing nice jeans and a button-up tuxedo shirt. I'm sure you can never go wrong showing up for a first date in a tuxedo.