He looks like summer!
Its too damn hot to always wear pants so in the summer it is time to break out the shorts. The great thing about shorts is they can be crazy colors, designs and patterns and still be stylish. They are shorts, they already are silly, so you might as well embrace it and really make the most of them. In the Essential Summer Fashion list you must have one pair of chino shorts that will raise an eyebrow. In my collection I have a light yellow chino short from J Crew (the color is "Butter") and I bought them for $20. What a great deal!
There are a couple things to keep in mind with the chino shorts. The crazier the color, the simpler the shirt. Wear a plain gray shirt or light blue polo with your crazy shorts... simple on top, devilish on the bottom.
Also, buy shorts... not capris. This means the short should stop before your knee. If you are around 6' that means that you should have the 9" inseam. The longer shorts that go past your knee makes you look shorter and like you are still living in the 90s. Even if you don't like showing your knees off, women think it looks good. So just trust me and find a pair of shorts that don't look like they are three sizes too big.
Don't match the colors! Don't wear blue shorts with a blue shirt, YUCK! Wear yellow shorts with a light blue shirt. Wear pink shorts with a gray shirt. Wear red shorts with a white button-down. Simple is the key.
Most of all... have fun with your shorts. Wear something that you feel comfortable in and makes you smile. If it makes you smile, it will make women smile.