A guy can wear almost anything (within reason) as long as he wears it with confidence. Granted you have some basic sense of style, and I assume you do since you are reading this, you shouldn’t be afraid to take risks. As long as you are comfortable in it and wear it confidently you should be fine. With that said, however, if there is a certain something that you've been itching to try but you think it may look ridiculous, you may want to consult a close friend before walking out the door. Nevertheless, the take-away message here is that if you walk down the street thinking you look silly; chances are that other people are thinking the same.
I once wore a pair of pink linen pants with a short sleeve shirt and a bow tie to a ‘business casual’ event and only got compliments on my unique sense of style (it was in the summer, of course). In a related story, a friend of mine (who’s name will remain anonymous for obvious reasons) after a night out on the town, was about to leave his girlfriend's apartment when he realized that he had lost his pocket square. As a replacement he stole a pair of lace panties out of her drawer and stuffed them into his breast pocket. They were the perfect shade of turquoise and it made his outfit. No one was the wiser and he actually got some compliments at work that day. Genius.
Please note that this post, nor any part of this blog, encourages the theft or wearing of women's undergarments. Thanks.
Yours in style, Style Blogger.