This time of year can make you feel like you're cheating on your clothes, no matter what you choose to wear. Bringing out a red plaid skirt immediately almost feels perverse. But, only wear your tanks and shorts and you'll no doubt end up cursing those jackets hanging in your closet as soon as the evening chill descends. You need a smart solution to end-of-summer layering, and one that leaves the diaphanous gray, white, and oatmeal linen for the ladies who work in the bead shop at the mall.
You can wear loose, lightweight items that will keep you warm without making you look like you've confused the month. With cotton anoraks, jersey skirts, and other natural-fiber separates, you'll be able to ace this awkward transitional outfit season while looking like a fashion plate, and not like you're on your way to a jam sesh in Kenny's basement.