Street View is a fashion series in which Isa Giallorenzo spotlights some of the coolest styles seen in Chicago.

I know I might sound repetitive when I say menswear is all about the right fit, but yeah: menswear is all about the right fit. Not too loose, not too tight, just right. Check out Freddie and Frank. Notice how their jackets hug their shoulders snuggly, how their pants fit them precisely, how their hems stop exactly where they should, giving their charming shoes a chance to shine. Some might say a tailor is a man’s best friend, and maybe they have a point. You don’t need to venture into bespoke territory, but why not alter pants or sleeves that fall too long? Such a small change, such a big difference. If you’re feeling casual—or broke—just alter them yourself by rolling up those bad boys. OK, now let’s say it all fits. Wanna take it to the next level? Color! The dudes above clearly don’t fear it, and neither should you.

See more Chicago street style in the Chicago Looks blog.