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  • I want to get a pair of wing tips I can wear often, but I can't seem to find any decent looking ones of any quality for less than $300. Help!

    - Jacob, San Leandro, CA

  • 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.

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