A very basic tip on date clothing choices for a buddy (and Pigs and Battleships gadfly) who needs it:
(1) 1st three dates: Do not wear the same shoes or the same jacket. Better still: adjust your style so you'll be rocking the high and the low. For guys, this means sporting maybe some vintage sneakers one day with a t-shirt and a casual leather jacket one day, some polished leather kicks and a dress shirt for a nice dinner on another night. For the ladies, miu mius switched up with colorful, stylish sneakers or wacky red shoes with flowers emblazoned on them, purchased in Chiangmai, Thailand. (Though I prefer dates who resist labels.) Also, try to avoid shoes with velcro straps.
(2) 1st five dates: do not repeat the same articles of clothing. Even if all your outfits involve a plain cotton t-shirt inside an open flannel button down, try to change up on the colors. Don't even repeat the same underwear. You never know if someone snuck a peek at your lower back as you were bending over to tie your shoe laces.
(3) Do not dish out your pet (beat-up Wade Boggs) t-shirt from the 9th grade until you're six months into the relationship, and even then make sure you're wearing that while washing your car or something.
(4) Do not wear imitation name brand goods on an initial date, even for ironic effect.
(5) Do not wear garish "dandy" shirts that cause headaches, or shirts that have seam problems. (Just a tip for myself.)