Finally, don’t be afraid to experiment and try out different color combinations to find what works best for you. The most important thing is to feel confident and comfortable in your outfit, no matter what colors you choose to wear. I once dated a guy who dressed impeccably. I loved his just shined wingtip shoes and large square watches and the Official Things I Do In My Spare Time Retro Bookish Reading Books Shirt in contrast I will get this short, tapered hair on the back of his neck. I decided then and there I had a thing for flawlessly dressed men and their regular appointments with the hairdresser. I dated another guy who didn’t even notice if his socks matched. He was lanky and untidy and disheveled. He had a few soft, well worn flannel shirts he didn’t mind lending me and did not even own a belt. I decided I had a weakness for shaggy haired, scruffy guys. One for how deftly he managed to make a perfect knot in his tie, the other for the uneven way he wore down his sneakers, the washed out color of his once blue jeans.