Founded in 2008, Hockerty is the e-commerce leader in custom suits and custom dress shirts, as we offer our customers complete freedom to design their own clothes by choosing from a wide range of styles and fabrics. 
When you think of men’s dress shoes, more likely than not, you immediately think of Oxford and Derby style evening shoes. While these are certainly common dress shoes, they’re not your only options. You’re far from limited to simply wearing low cut shoes to go with your outfit, whether you’re getting dressed for a lunch meeting, an evening out, or any occasion that requires more than just jeans and your standard rugged footwear. The great thing about men's boots is that you can either dress them up or dress them down, depending on the occasion and of course, your personal style preferences.
Chelsea Boot
What it is: The chelsea boots that have royal roots. Queen Victoria’s shoemaker, J. Sparkes-Hall, created the easy to wear style to replace the existing and inconvenient lace up riding boots of that era. The Chelsea Boots are characterized by elastic side panels and a loop or tab at the back of the boots. These special features make the ankle boots easy to slip in and out of.
Today’s modern version of the boots come in a wide range of materials, silhouettes and color combinations. Of course, traditional black and brown with matching colored elastic gussets are staples for the Chelsea Boot. However, fashion forward men can step out in a bold colored pair, such as blue or burgundy with contrasting colored gussets, brogue perforations and even a wingtip toecap design. You won’t lack for choice when it comes to Hockerty color combinations, materials and style details. It’s no wonder that the Chelsea Boot remains to be one of the timeless footwear staples.
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How to Style it: A versatile style, you can wear the Chelsea boots with almost anything. Wear a brown three-piece suit with matching brown Chelsea boots. Pair a double-breasted suit with a bright red pair of Chelsea boots. For a subtler take, wear an all-black ensemble of a jumper, trousers and coat with dark brown Chelsea boots for. Now, for a more casual look, don’t hesitate to wear your black Chelsea boots with distressed jeans.
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| Brown Tweed 3 piece Suit & Brown Chelsea Boots | Grey Striped Double Breasted Suit & Burgundy Boots |
Chukka Boot
What it is: The Chukka boot is another ankle-high boot. What makes the Chukka boot stand out is its open lacing up the ankle with two or three pairs of eyelets. Yes, only two or three pairs of lacing eyelets. Anything more or less and your shoe is not a Chukka boot. Chukka boots are also set apart by its rounded toe-box, its thin rubber or leather sole and the fact that the boots have two distinct parts that are usually made from a single piece of leather. The boot’s unique style is matched by its unique name. It is said that the Chukka boot derives its name from the game of Polo. “Chukka” or “Chukker” refers to the period of play in Polo. The Chukka boot is also otherwise known as the Desert boot.
Regardless of its actual origins, throughout the years, the Chukka boot has risen in popularity beyond the polo field and the closets of polo players. Gentlemen today have a vast array of options when it comes to their own Chukka boots.
Chukka boots look equally great whether they’re made of leather or suede or even a fashionable combination of both materials. The distinct style can also feature brogue perforations, a plain or wingtip toecap, a medallion on the toecap, subtle blind eyelets or metal grommets on the eyelets, a one piece or two piece facing along the ankle area and of course, shoe laces, just to name a few of the its style details. Like we said, the options to make the style your own are quite vast.
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How to Style it: If you’re looking for a little style inspiration when it comes to your Chukka boots, look no further. Brown leather Chukka boots with a navy checked suit? Check! Chukka boots with dark chinos? Why not! Black or brown Chukka boots with blue or colored jeans? Sure! Yes, the Chukka boot can go with almost any outfit. In fact, not just any outfit, they’re also appropriate for almost any occasion.
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| Blue Pants & Grey Polo Shirt & Brown Chukka Boots | Blue Checked Linen Suit & Brown Chukka Boots |
Dress Boot
What it is: Serving both a rugged vibe with a refined flair is the leather dress boot. The ankle length boots feature an open lacing with multiple eyelets, as well as an optional pull loop and metal hooks that give them a casual edge. While the thin rubber or leather sole, fine laces, smooth leather, as well as elective style details including brogue perforations, a cap toe, and two piece facing give them an air of elegance. It’s another perfectly versatile boot option that you can dress up or dress down, depending on where you’re going and the outfit you’d prefer to pair it with.
As with the Chelsea boot and the Chukka boot, there are countless design elements that you can choose to make the dress boot your own and fit your unique personal style. Choose the exact style that perfectly complements your preference and wear it with your suit for a night out, trousers for a business meeting or jeans for a casual day.
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How to Style it: The dress boot is a great alternative to the traditional and usual oxford and derby style leather shoes. Whether you prefer a single tone black or brown leather dress boot, or perhaps a two-tone dress boot with either a contrasting quarter, vamp, heel cap or even a contrasting tongue, the dress boot is a fashionable and unexpected choice to go with your single breasted or double breasted suit. David Beckham who, to this day, is considered one of the best dressed gentlemen in the world, has a huge affection towards dress boots. Copy his style and combine double-breasted tweed suit, paired with dark brown leather dress boots. For a more casual occasion, wear a simple button down shirt and trousers with suede dress boots for an added flair.
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| Tweed Double Breasted Suit & Brown Dress Boots | White Shirt & Blue Pants & Blue Suede Dress Boots |
In case we still need to spell it out, it’s time to step up your style game and get suited and booted in a pair of men's custom boots.