Dressing For a Date

A week or two after I ended things with the first guy I dated for a long time (ie. my first "serious relationship," not my "first guy"), I was so done with protocol. I was basically a rebound waiting to happen. What did I know from rebounds back then? Either way, I think the next up appreciated this, because he had been dating for awhile and a "serial dater" on top of that. He was ready to break the rules and have a good time doing it. Because we had a conversation about what formalities do and do not mean during our first date, he showed up to our second date with wet hair, one too many shirt buttons undone, and shoes that I can only describe as clogs. I'm not sure if he was trying to make a statement, make fun of me, or simply just got carried away.

What is appropriate attire for a date? Should you "dress up?"

Put it this way, no one is the authority on "what to wear" on a date. (In some circles you're "supposed to" wear hat/suit/tie on a first, and sometimes consecutive date/s, and others scoff at that idea.) The barometer is "what message am I trying to send?" Do you dress up for a job interview? Why would you not want to put your best foot forward on first/second date? Do you respect the person you're meeting to put yourself together? Do you respect yourself?

What sort of date are you going on? If you've arranged an informal coffee date or the like, you obviously don't want to show up in black tie formal wear. If you're doing an activity and it's a beginning date, you can get away with business/dressy casual. (A guy can always take off his tie and jacket. As a girl, keep in mind, "You can never be overdressed or overeducated." I believe that's Oscar Wilde.) In the frum world we have some further clothing delineations (at least for girls, it's a lot less complicated for a guy). Wedding attire, fancy Yuntif/Shabbos, casual Shabbos, Chol HaMoed wear, nice weekday garb, sporty apparel, etc. Just be practical. Do you really want to be traipsing around in high heels? Heels work for a lounge/dinner date but get in the way during most activities. As do black hats. (Unless you wear your hat everywhere, so that'd be indicative of a hashkafa I guess.)

I'm not sure why this isn't intuitive, but it's never okay to wear a shirt with a fraying collar/sleeves, badly scuffed shoes, a pilling sweater, severely creased clothing, anything with a hole, a stained tie, and the like. There is a difference between dressing casually and being put together and casual and "I can't be bothered." You don't want to look like you don't care how you look/how you represent yourself and/or that you don't notice what you're wearing. Your outward appearance is the first thing people judge you on, whether you like it or not. Hopefully it's not the only thing being judged or carry too much weight, but you can definitely lose or pick up some points here.

I think how you dress is about respecting yourself and this process. We're not just hanging out after school and going for ice cream. Putting yourself together means you put thought into getting ready for the date and put forth effort into the shidduch.