Carson Street Clothiers: New York

Where: New York's Soho
Style: Upscale Comfort
Brands: Carson Street, Eidos, Orlebar Brown, Blind Barber
Invest In: Cashmere Blazer 

Carson Street Clothiers consistently offers a selection that is a goldilocks of menswear — not too stuffy, not too trendy. "They are considered a leader in menswear curation and taste-making by simply blending classic tailoring with more progressive, contemporary sportswear," Dolan says. "Regardless of your lifestyle, every man should feel comfortable taking it up a notch by wearing a sport jacket to a patio. The gentlemen at Carson Street Clothiers will show you how." Those gentleman, the two founders who also happen to be ex-attorneys and former law-school roommates, understand that a little bit of everything and some custom-fit tailoring is the perfect formula for timeless sophistication.