the gray hoodie.

It may be 3 in the morning, or for ultramarathons even 2am, I believe that it's no reason to look sloppy and unkept.  I would say that the most versatile and yet fashionably practical thing to own, as someone who sends of a loved one in the wee hours of the morning, is a gray hoodie.

It's something that keeps you warm so early in the morning.  You can wear the hood to camouflage bedhead, and wahey it also doubles as insulation (with that little fact of 80% or some significant percentage of your body head escaping through your head).  Throw it over a tank top for the morning chill, and discard as the day wears on.  You can wear it to top jazz pants, cropped shorts or what have you's - a skirt, if you really want to play cheerleader.  And since it's a hoodie, you can disguise the non-sportiness in you. Because yeah, it's not a cotton-lined boyfriend blazer.

The best part about it - it's grey.  It will go with anything.  It can even go with your husband's singlet (but I doubt if you'd go that far).