In a jeans-and-T-shirts era, it isn't easy being dapper. Here are some of the challenges the Summer of Dresses women and the Summer of Dapper men have encountered so far:

"Shaving my legs." -- Meghan Wilker

"Wrinkles. Thanks to Summer Of Dapper, I can now put 'converting a coffee table into an ironing board' on my list of skills." -- Jared May

"On windy days, it's a challenge to maintain decency." -- Sasha Westin

"Having the time to plan out a look and make sure everything is pressed and ready to go. I always have to try on about three to four different tie, shirt, vest, pant, shoe, hat and sunglasses combinations. Then edit and make sure it's as perfect as possible." -- John Wallace

"The most difficult part for me has been the maneuvering of wearing short dresses while riding my bike without offending the entirety of the Minneapolis Greenway." -- Nicole Weiler