"I will be going on a date this week and were going to be walking around Venice beach and the Santa Monica Pier. I have no idea what to wear since it will be around evening/night time and by that time the weather is really cold, so I can't wear a dress or heels or sandals. I would like to dress comfortable clothes. I'm not a fan of flats, though i wouldn't mind wearing tennis shoes since there's going to be a lot of walking, I also have a couple of pair of black boots. If it helps, I do have a woman's blazer jacket but I also wouldn't mind a sweater or so..I could really really use your help on this.."
Taking all of her restrictions into account, here are three looks I came up with (click on any photo for more information). For this first look, she could easily throw on a jacket she already owns over this top for more warmth, and I know she said she didn't like flats but I included them as an option just in case.:
This second look could again be warmed up even further with the addition of a jacket she already owns.
I threw in a pair of inexpensive cognac boots from Target, but black would also work in this situation since she already has a couple of pairs.