It can be daunting to find a pair of stylish shoes strong enough to take a daily beating. But the task is not impossible. Bostonian, which has been crafting quality men's shoes for more than a century, offers a rakish take on the traditional wingtip. Available in black and oxblood full-grain leather or chocolate suede, the brogues will look just as good with your suit and tie as they will with jeans and puffer vest. $100 (with free shipping), at Zappos.com.