Get thee over to What a Woman Needs In her Wardrobe for two excellent posts that speak to the issue of style and the individual...
Fashion is Stupid
In both Ms. Allie states some hard truths -- and give some great advice on how to deal with them!
Anyway you slice it, it all comes down you this: You HAVE to dress - you might as well find a way to do it that both presents you in the best way possible and is true to who you are.
No not easy, I know - but, damn it, you ARE worth it! ;-)
(And by the by - while you're over at WAWNIHW - check out her post giving good advice to stay at home moms: Mall and SAHM. Honey, those tips can work for anyone! ;-) And her list of suggested shops is right on and will work as well for the 50+ gal!)