Today, I was wondering why men wear skinny jeans. Skinny jeans are a difficult trend to pull off for both men and women. Skinny jeans tend to work best on very slim figures; however, many women can wear them if they pair the jeans with a dress or long shirt. I love wearing skinny jeans in the winter because I can tuck them neatly inside my furry boots - fashionable and warm! So, this brings us back to the question - why on earth would men wear them? Men look best when wearing fitted jeans.