So here's my most recent roadblock. I'm an hourglassy/pearish deep winter and, while I feel perfectly fine rocking out some bright colors and pencil skirts at the office, that's not my weekend personality. I am much more of a tomboy and need my jeans, combat boots, and gear-ish jackets to feel comfortable. I also prefer the low-key colors when I'm not at work.

This goes over fine in the winter, when it's easy to do jeans, boots, and a killer coat and be done with it, but I struggle with spring/summer. Summer colors don't feel right or look right, and it's harder to do a "tomboy" shorts-and-tee combo without ending up just looking like a boy -- and a chubby boy at that, since tight/fitted clothes are impossible in 80+ degree summers.

I have a couple of things worked out... I just bought an optic white windbreaker and some plain white tees that I like to pair with denim and navy, and I really like how that turned out. Last year, I also liked doing neutral outfits with a bright bag to bring a little color near my face. Still... it seems like the seasons and my style are working against my body lately. Bleah...