Chicago can become very hot in the summer, often breaking 90 degrees. If you want to maintain a sense of fashion and still feel comfortable, don't wear clothes that are heavy and layered. Keep your outfits light, and you'll enjoy the outdoor weather. Keep jackets at home, and don't even think about legwarmers.
In 2009, Chicago women shouldn't be afraid to show off some skin, because it's practically unavoidable if you want to be comfortable during the summertime. The most popular fashions for women are sundresses, skirts and sandals. A very recent fashion trend is shorts. Avoid midriffs--the 90s are long gone. But show off your legs and arms to look fabulous in Chicago.
Guys should always keep a short-sleeve shirt nearby. That will be more comfortable than a pair of khaki shorts. If you must wear shorts, don't get the ones with huge cargo pockets on the side. The trend is to wear shorts that are higher than the knee. And don't wear socks. Slip-on shoes are comfortable and fashionable. When all else fails, take a look at the guys in the band Vampire Weekend.
The main rule of what to wear to the beach doesn't refer to anything below the neck. The most important beachwear is actually sunglasses. If you don't have sunglasses, you're going to squint. Make sure to get a good pair of sunglasses, and then wear whatever one-piece, two-piece, shorts, sandals or whatever kinds of clothes you feel comfortable in.
