Ive owned both. I found myself not wearing the 288 as much in casual situations as it is very dressy for a pam. It is beautiful and highly accurate.
I liked the blue accents with the 253 and the case shape. I prefer the luminor case to the radiomir also. However, due to the size of my wrists and probably the strap dimensions, it tended to roll over the top of my wrist. I have an 8.5" wrist though.
I guess it depends on where you will wear it more, but to me the 253 is very casual and sporty, and the 288 can be dressy with black croc, or more casual with brown leather. I liked them both, so I dont know if I could make the decision.