Popsugar Fashion Travel What to Wear in Boston What to Wear in Boston, According to a Fashion Expert December 28, 2022 by Mekita Rivas View On One Page Photo 17 of 17 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 17 J.Crew Winona Penny Loafers J.Crew Winona Penny Loafers ($178, reg. $198) J.Crew Winona Penny Loafers $178 from jcrew.com Buy Now Previous Next Start Slideshow TravelShopping