Hi ((((Jenn)))) Happy (belated) Birthday!
I really appreciated and loved your post. It sounds as if you are looking for some guidance...how about going to one of the larger dept stores and making an appt to meet with the resident personal shopper / stylist? It doesnt cost anything and you can give he or she all the details so they can help you find tbe best look for you!

I shy away from recommending individual stores and or boutiques because I dont exactly know what look you are trying to achieve...one of the things that really helps me, though, is to flip through the current lifestyle and womens magazines to see if anything catches my eye! A certain look, trend, style, etc. Also if you want to be a little fashion forward, check out the Paris collections for next spring and fall, online. Certainly you wont want to dress the runway,but designers' collections are very inspirational!

Also accessories are a great way to spruce up your wardrobe and give it a fresh look!

Also have you considered a new hair style? Something fresh and new but not drastic. Perhaps bangs, a little update, even a sprinkle of color. That can be fun!

The most important thing is go with what you like and feel comfortable in. You can never go wrong that way. Your confidence and comfort will shine through no matter what you wear!

Good luck and have fun!
Let us know how it goes!

Rose