Varying slightly from silhouette to silhouette, we’re going to help you find and lace up a pair that’s sturdy enough for the season’s elements, but sleek enough to pair with your favorite suit. That’s rule number one too; if you’re wearing that well-tailored suit, your boots have to reflect that. The dress boot should be something with a finer grade of leather, a slimmer cut and a smaller, thinner sole. There is a time and a place for Red Wings, this isn’t it though.
The Captoe Boot
The first style of dress boot to consider is a standard captoe boot. Mimicking the style and dressiness of a prototypical dress shoe the most, a sharp captoe boot can be perfectly at home in any office. Keep them with a high shine, just like the rest of your dress shoes, and it’ll be ready for office duty for years to come.
The Brogue or Wingtip Boot
Up next, the brogue boot. Just like your trusty standard wingtip that’s getting you through the weeks, these boots are undeniably stylish. On first look, they mirror the brogues found in half the cubicles at the office, but further examination reveals a perfect marriage of elegance and function. It can be our little secret that those beautiful perforations on your brogues actually belong to a pair of boots, laced up with some new found confidence. Looking for extra credit? The brogue boot looks terrific with both chinos and denim as well.
The Distressed Boot
Since winter is forthcoming, you’re no doubt going to need something that can withstand the weather. When you've got some nasty rain or snow to cut through but still need (or want) to suit up, reach for a pair of distressed boots. The rougher leather and slim soles work with any of your brawnier fall suits, and the fact that these boots are more beat-up than polished makes them good for bearing the brunt of winter. Distressed boots work best with heavyweight suits, your tweeds, flannels and textured wools are a good play here. They’ll complement your boots with an equally sturdy yet rugged punch. If your boots are going to see some weather (and any good boot should) don’t forget to take proper measures to treat and protect the leather.
The Chelsea Boot
Back on trend from its heydey in 1960’s, the Chelsea boot blends just the right amount of rock ‘n roll with class to create the perfect balance of office and after-party. The Chelsea boot features a silhouette that is laceless by design and can be pulled on or zipped up from the side. Often utilizing a classic color palette of browns and black and in supple leathers, we also can recommend a nice suede version because of it’s versatility (try it with denim and an overcoat). The beauty of a Chelsea boot is its simplicity and sleek profile. From its lack of laces to the minimized shape, the boot has lasted primarily because, well, it's easy to wear time and time again. Pairing it with a suit is not only super cool but practical as well. We recommend keeping the suit solid, but a subtle windowpane pattern could add that extra flair you might be looking for. One other bonus, the Chelsea boot’s exceptionally cool look is the perfect way to take your daytime suit into the evening.
With the wide range of boots on the market, the decision won’t be easy. Take a look at your wardrobe and see what pair or silhouette makes the most sense for your daily rotation and take the plunge. If you’re a boot novice, we recommend starting with something classic first, a clean lace-up captoe or a Chelsea boot is about as dependable as you can get.