A few pairs of Dockers khakis will be good, but opt for the flat panel fronted pants instead of the pleated front style. The pleated style tends to make you look older and kind of out of fashion, and the pleats have the tendency to form a “pup tent” when you sit down, not a look that you probably want. You can read more about the differences between flat panel fronts and pleated front pants here Here are some khakis in the traditional color and here are som grey-green khakis
Of course a nice fitting (not to tight, not too loose, not to long) pair of 501 jeans that has already been faded (the brand new ones look too stiff) with a pair of neutral colored low top Converse sneakers (gray, black, olive, maroon, white, but none of those crazy neon colors) with a loose fitting T-shirt in a solid color (try to avoid graphics) or an untucked polo shirt in a nuetral color are a fairly classic “college guy” look. You can see that here You could wear this outfit on a very casual date, but do not wear this outfit if you are going out to dinner, or to a play or to your date’s parent’s home (unless it’s a barbecue).
You can also wear a nice vintage or new (understated, not loud) Hawaiian shirt for a lot of functions. Yes and No (unless you’re going to a luau).
There’s quite a few different kinds of cotton shirts that can be worn with jeans (the faded 501’s or slightly dressier ones like these relaxed fit boot cut jeans) like this long sleeved shirt or this short sleeved shirt or a Ralph Lauren-style polo shirt in either a neutral stripe or a neutral solid. Or even a shirt in a Rayon/Polyester blend in a nuetral solid color (like burnt orange, chocolate brown, navy, or putty)
Good luck and have fun : )
And like some of the others have said, get yourself a nice looking, reasonably priced, comfortable pair of dress shoes that can be worn with a suit or dress pants or even a nicer pair of jeans. Here’s an example Try to avoid shoes that are too trendy looking, such as some of these shoes that have a super long pointy toe or a giant boxy front (which tends to make your feet look way bigger than they are). Avoid this and these
And for other casual and/or athletic shoes, try to avoid anything _flashy. That means color-wise, decoration-wise or size-wise (no giant shoes that make your feet look like a size 13, unless you actually are a size 13). Yes, Yes and Yes and Yes and Yes and No and No and No and No (unless you are in your 50’s) and No (unless you’re in your 70’s)
In some areas of the country (find out if yours is one of them) it’s perfectly OK to wear a nice pair of leather flip flops (with no socks) with jeans, but make sure that your feet are impeccably groomed. Cut your toenails, file your toenails, clean the dirt out of your nails, and exfoliate your foot skin, wait until your blisters, flea bites or warts, have heeled etc. Disgusting looking feet is one of the #1 turnoffs for women. Keep your feet clean and your socks clean and your shoes clean!!! Yes and No Even if your feet are lovely, do not ever wear Tuva Sandals or Crocs or Birkenstocks