The 12 best-looking dress shoes you can buy for under $500

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Regardless of where you work, every guy needs a pair or two of reliable, quality dress shoes in his closet. Even if you don't live the "business-professional" lifestyle of a Wall Street executive whose footwear must always be top-notch, having at least one sharp pair of wingtips will ensure that when a close friend has a wedding you aren't the guy showing up in Chuck Taylors.

We've covered dress shoes available for under $200 and under $350 before, but if you have the money and are willing to pay a little bit extra for a higher quality product, there are tons of good-looking shoes that are available to you. Below are our 12 favorite oxfords, monk straps, loafers, and more available for $500 or less.

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Allen Edmonds

The Park Avenue Cap-Toe Oxford offers a classic, timeless look that has proven to exude success. It was the shoe of choice for Presidents Reagan, Clinton, and both George W. and H.W. Bush at their inaugurations. You can't get more professional than that.

Allen Edmonds Park Avenue Cap-Toe Oxford, $395, available at Amazon and Allen Edmonds.

Crosby Square

This Monk-Strap from Crosby Square is a great, versatile shoe to add to your arsenal of footwear. It's a pair of shoes that can work well both at the law office and with a nice pair of jeans on the weekends.

Crosby Square‘Diplomat’ Double Monk-Strap Shoe, $395, available at Nordstrom.
Crosby Square 'Cambridge' Cap Toe Oxford, $395, available at Nordstrom.

Paul Evans

Paul Evans was founded by two former finance guys who realized that no one was making an everyday dress shoe that met their needs. With high quality products and an impressive price point, founders Ben Earley and Evan Fript have positioned their product as an alternative to the usual names you see rattled off in men's footwear.

Paul Evans The Martin Wholecut Oxford in Oxblood, $389, available at Paul Evans.