Dressing for a blind date

Q. This may be a strange question, but what is a safe look for a first date?  I am a groomsman at a college friend’s wedding next month in Memphis, and he (and his fiancee) claim there will be two women there who they think they “can see with me.” I’ve scheduled to stay a few days after in case they’re right, but don’t know what to bring after the formalwear for the wedding.   
A. The problem with dressing for a first date is the number of unknowns you have to deal with. You don’t know the person. You don’t know that person’s tastes and preferences. It sounds like you may not even be sure where you are going on the date. All these can create confusion. And, while this technically may be a second meeting, this is truly about first impressions. This is where she sees what you think you should look like. If ever you really want to start out feeling good about yourself, it is on a first date. These are definitely good reasons to pay extra attention to what you are wearing.
First, the biggest unknown is the personality of your partner for the evening. Since you are, at least to some extent,  in the dark about that person, you are faced with the immediate disadvantage of not knowing what look you should try to parallel. Unless you plan ahead of time that the place you are going to is quite dressy, you don’t want to risk being overdressed in a dark suit; neither do you want to come off as inconsiderate by underdressing in jeans for the occasion.
So, probably your safest choice is a nice pair of dark dress pants or well-pressed chinos. Add a navy blazer (which can be removed if your date is not dressed up, but which will be dressy enough and complimentary to most outfits suitable for an evening out). Or, if you intend to make it clear ahead of time that your evening’s destination is not a dressy place and if you are not comfortable with an Ivy League look, you might substitute a subtle wool tweed sports jacket for the blue blazer. Either jacket shows you cared enough about your date’s feelings to make an effort, which, you should know, is almost always appreciated.   
When it comes to choosing a shirt, you have a lot of options. I would skip the white shirt and select instead something in a flattering color, such as light blue (a strong first choice) or a soft shade of yellow, or maybe a pale pink. Blue-and-white stripes are another safe bet. As to the shirt’s style, even if you own nice cufflinks, a somewhat dressy French cuff shirt is probably not a good choice, because of its one big disadvantage: if you discover that your look is overly dressy for the way your partner is dressed and if you want to remove your jacket, then the French cuffs would also be too formal. Much safer is a pinpoint Oxford cloth shirt with a button-down collar and standard barrel cuffs. It is always tasteful, and it also eliminates any problem that might arise from choosing too large or too gaudy (new rich?) cufflinks. Another plus: if you have worn a tie that seems too dressy, you can take it off and stash it in a pocket, unbutton the top one or two buttons of your shirt, and maybe even turn up the cuffs a fold or two (which doesn’t really work with a French cuff shirt).
Pay attention to your accessories as well. You should know that women (and also potential employers) pay more attention than you might think to a man’s shoes. Your simplest and safest choice would be well-polished loafers (not as dressy as lace-ups nor as casual as deck shoes or any form of sneakers). Dark socks always work; but, unlike dressing for a job interview, if you feel my advice is too conventional and not adventurous enough for your personality, adding a pair of today’s colorful patterned socks would be more free spirited and still not brand you as too outlandish.
All elements of good grooming are important in the dating world. Be sure you have a good haircut, don’t wear too much jewelry, and use very little fragrance. Obviously, in order to get her interest to have this first date, I suggest you follow the grooming suggestions above and the specifics of the wedding attire to the letter . . . That day is supposed to be about the wedding couple; your personality and your ability to follow those rules should make you stand out there and then. I hope this advice will help on meeting #2/date #1. Then, even if all else goes wrong during the evening, at least you know that you did your part and you looked right. Have fun. 
Categories: Male Call