Romeo sweatshirt, $35.95, at Zara. This Champion sweatshirt pays homage to the sportswear roots of the heritage brand, and is made to last. The more you wear it the better more broken-in it becomes.

Ronning’s sweatshirts are all part of this wider, comfier episode. But Cosy Boys also run the risk of going too big, and too boxy. The Michelin man is a tired marketing ploy, not a menswear cue.

The quarter-zip sweatshirt comes in 17 colors, including gray, green, pink, black, and white in sizes S through XL. It features a breathable and soft cotton-blend fabric with a fleece lining ...