This is not a problem for most grease monkeys. Let’s face it, you wash your hands with a good industrial degreaser, find a clean pair of overalls, take your mostly clean dress shirt off the hanger and it’s time to party. This manner of dressing should be quite satisfactory for any woman looking to be involved with a grease monkey. For the rest of us we may need a little more direction.
For the farmer woman, dressing is easy. Put on your favorite western boots, the ones you scraped off the manure from the soles. And any ole dress will do as long as you got out the horse smell. Hey, guys may like to ride you like horse, but they don't want you smelling like one.
Okay, maybe everyone needs some advice for first-date dressing.
While many are inclined to put their best foot forward and get all decked out on the first date, you hopefully have more than one nice outfit. If you go on “date one” wearing your best clothing, this means that date two has to be "less good" in terms of how you are going to look. Sure you don’t want to miss out on a “date two” that never comes because you weren’t wearing your “best” outfit on date one, (you may want to check out the math here) but if Mr. or Ms. Right is that shallow, you might be better off alone than out with a jerk.
Actually, it is important to put your best foot forward. As the saying goes, “You have only once chance to make a first impression.”
Because you really don’t know what this person likes or expects, it may be best to avoid extremes. This is a good rule in general, but even more so when making a first impression. You could argue that, "If this person doesn’t like me for who I am, then too bad for them, because I don't like compromise!" Of course this attitude may be why you haven’t been in a meaningful long lasting relationship… ever.
Compromise may be something to consider in life if necessary. So how does this relate to what you wear on that first date?
Try to be a little more conservative. This is not the date to wear your new, sheer blouse with the nipple cut outs. Actually, that blouse will often get you to date number 2, however, generally speaking, "too wild" may turn off too many prospective dates while conservative dressing will not offend anyone. Perhaps a nice pair of jeans with a nice sweater (in winter) or an attractive, classy blouse (in summer) is better than your jeans with ten holes and frayed all over (you know the expensive ones you bought at Bloomingdale's) and the buckskin vest with all the frilly dangles hanging down.
You guys may want to consider wearing a shirt that doesn’t shout out, “Ring around the collar!” Clean really works! Jeans that allow your belly to bulge out the front while your ass crack reveals, well... you ass crack, is not a good first impression outfit. Instead, try a conservative shirt with well fitting jeans that doesn’t accentuate your bodily asymmetry (aka your beer belly).
When it comes to dressing for that first date it really is all about being a bit more conservative, neat, clean and classy, unless you are dating that grease monkey or farm gal.