Ok, since I have no idea what kind of style your looking for, here's a couple tips that I follow.
Nice dark jeans, not destroyed or anything, I have some earnest sewns on right now, and they're so nice.
Some nice polo's, I wouldn't get really pastel colors if your just transtitioning.
Some nice slim fit hoodies, ideally vintage.
Get yourself some sandals, and some sperry's.
Of course those idea's could be way off for your style, but it looks best.