Popsugar Fashion Fashion Trends The Biggest Sneaker Trends to Wear and Shop For Fall 2019 The Biggest Sneaker Trends to Wear Right Into 2020 3 October 2019 by Avery Matera View On One Page Photo 27 of 42 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 ShoppingFashion TrendsUltimate GuideFallSneakersFall FashionShoes