I think dating someone else to make you will beter will be addressing symptoms rather than the root issues. It could also backfire if you go faster than you can adapt to the new situations.
It sounds like you have some good security in your relationship since you know you are connected together on more than a physical level. It may be that he doesn't feel drawn to the tom boy look, but I know a lot of guys who are.
If your husband does go on a date, I think it is good if you find something to do suring tat time that makes you feel good. Watch chick flicks, go to a movie with a friend, take a relaxing bath, do cross words, or whatever you like to do that makes you feel good. A date is not a bad idea, but I worry it will be done to avoid dealing with the feelings you have.
I think you should find someone you want to date because they feel a need or a desire. Don't rush it because you could wind up in a bad relationship.