Consider Your Entire Wardrobe

Alexander Wang Windbreaker Bomber
Buy It Now at Barneys, $229

It's easy to be distracted by a deep discount on a designer item, but will you really wear it regularly, even at 75% off? Chances are an item went that deep on sale because the quality just wasn't as good as the other things in the collection, or, like many designer pieces, some guys just can't pull them off. With designs like asymmetric zippers, unconventional fabric combinations like nylon and leather, or cuts made to hang off the body in a different way than you're used to, buying designer gear is often a personal thing that varies from person to person. If you can see the piece working well with a lot of stuff you already own, go for it. Otherwise, leave it on the rack.