Like many things in my life, this change was one I knew I’d instantly remember: “It’s time to dress like an adult,” my friend Ryan said, in a surprisingly non-insulting manner. I knew it was time to change the way I dressed. I went from cargo shorts and AEPi shirts year round to polos and shorts in the summer, and a v-neck sweater with a button down in the winter.

It was a slow process, and while I am not the best-dressed person in every room, I am typically the most varied and coordinated in what I wear. I think it’s added a lot to conversations and helped me to feel more confident, and I’d like to share some tips to help you add personality to your outfits. Note: most of these are aimed at men as I only dress like a man, but feel free to provide input.

• Accessorize. Whether it’s a watch, hat, fun undershirt, sweater, or other item, an accessory is always a great idea. Lately I’m big on fun socks — TheTieBar.com and Express both sell great, cheap socks. I also love a good tie clip (also available on The Tie Bar for cheap) and different color yarmulkes/baseball caps.
• Mix it up. Let a button loose in a new place, roll up sleeves you normally don’t, pair odd colors together. Sometimes things look stupid, but sometimes you make a great fashion find. My favorite was wearing a shirt at the University of Florida Chabad last summer, and having someone tell me my undershirt was a bad choice with my button down shirt. Instead, I made a transformation into a “fundershirt” as I called it. I went from looking ridiculous with a thick undershirt, to having a pink collared shirt unbuttoned with sleeves rolled up and a yellow undershirt brightly giving my outfit an extra oomph.
• Don’t worry about it. Sometimes things look stupid, and that’s okay. In fact, I would argue dressing like a schlub can be a great way to display a different sort of confidence. If you mismatch and someone points it out, great, thank them for pointing it out and laugh about it. JDate released a study a month ago, and most people find style negligible anyway, but a sense of humor and confidence will go a long way no matter what you’re wearing.