How To Wear: Wedge Sneakers I’ve been on the fence all winter about this trend. It’s definitely one of those “Love it on others. Not sure about me.” However I’ve made the decision to go ahead and do it! So, how do you pull off the wedge sneaker look in everyday life. To me, this trend is perfect for the weekend casual ensemble. Pair it with leggings, a sweatshirt, beanie, and tote. Keep it street chic!