I've always been into a gal who is well-put-together in office-looking attire.  
I used to work in an office environment in my previous career and always loved seeing the gals in their nice white/colorful blouses and skirts.  Heels were always nice, but they almost all had flats at their desks.

It's that fantasy of getting it with a gal that could very well be someone you worked with or see in a normal day.  

Used to date a blonde nurse who was also going to law school in the evenings. She was in the process of switching careers.  She always looked great when I picked her up at school or work.....dressed in those heels and suits.    

I bring the lady something I think she'd look good in.  Chicme.com has outfits for under $20.00 so I usually get two or three cause i never know how they'll hang on a particular lady.  G strings also are nice.  i enjoy play time with a lady in a dress.  Hides any imperfections and without a bra usually looks very hot.