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 wing tip. 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
Wing tips (or Brogues as they're called across the pond) originated as a shoe for Scottish Highlanders who trudged though bogs and required shoes with drainage. Today the 'brougeing' holes are just for show.