The advantages of ankle boots are that they provide more protection from the elements than shoes, but they're not annoying or prohibitive in the ways that some taller boot styles are.
Score yourself a pair of black, simple, classically-styled ankle boots, and they'll work with a variety of casual outfits, and serve you well for years to come.
On the other hand, if you want to make a lasting impression and don't need quite as much versatility, opt for a pair that has a little something extra. It can be side zipper, a bicycle toe, or a distressed upper. The "what" doesn't matter as much as the "why," and that, simply, is because you can.
Unlike your everyday shoes, you probably won't wear a pair of ankle boots every day. They don't need to work with everything in your closet. Try something new, and see what works for you. If you find a style you really like, the rest of your wardrobe may follow suit.
Whichever route you take, men's ankle boots, like the ones pictured above, are a great variation on the standard dress-casual shoes that a lot of guys are used to wearing. While they're not dressy enough for a suit or a formal setting, they'd be a great match for most dress-casual and casual pants, and they'd bring your favorite jeans to a while new level.
Available in mocha or lead, these boots ring up at just under $300 per pair. Next: Suede Boots