Eric Lynes, the man currently at the helm of this almost-century-old Canadian haberdashery, might be the world’s foremost expert on gentlemen’s hats. (Seriously, ask him anything.) With a wide brim and a shaped crown, this exclusive felt style is a cool way to keep warm. Style Name: Madewell X Biltmore Shaped Wool Felt Hat. Style Number: 6107657. Available in stores.