Popsugar Fashion Fall Fashion The Biggest Sneaker Trends to Wear and Shop For Fall 2019 The Biggest Sneaker Trends to Wear Right Into 2020 December 2, 2019 by Avery Matera View On One Page Photo 27 of 43 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 27 Madewell Madewell Sidewalk High-Top Sneakers ($98). Madewell Sidewalk High-Top Sneakers $98 from madewell.com Buy Now Previous Next Start Slideshow Fall FashionFashion TrendsSneakersShoppingUltimate GuideShoesFall