Clockwise from top left: Polo Ralph Lauren knit flag cotton sweater, pant and sneaker; Polo Ralph Lauren cotton shirt, Team USA sweater vest and denim skirt; Polo Ralph Lauren one-shoulder ...

Lauren Ralph Lauren Quilted Logo Vest, $64 (was $165) at Macy's. Shop It! The preppy New England aesthetic will never go out of style, and this vest embodies the timeless look.

The Best Argyle Sweater Vest: Our Legacy Formal Sweater Vest, $305 The Best Cricket Sweater Vest: Polo Ralph Lauren Team USA Sweater Vest , $ 298 $199 The Best Cardigan Sweater Vest: Gap CashSoft ...