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If GQ were a barbershop, it would be Irving Park Barbershop. This dapper North Side cuttery is throwback charm at its finest—and we're not just talking about the decor and Bob Seger jams. Come here for the vibe, 5-star haircuts, and classic shaves. If you're lucky, you'll snag a brew while you wait, or even a visit from the shaggy shop dog.