Men’s Ankle Boots

Looking for a pair (or two) of handmade men’s dress ankle boots?  RebelsMarket offers you an array to choose from. With versatile pairs fit for different personalities, seasons, occasions, and budgets, you are sure to find several that suit you.

 How to Shop 

Unique ankle dress boots are a great addition to every man’s wardrobe. They are not only stylish but comfortable too. When buying them, always have your tastes and preferences in mind. You might want to jot down some notes as we break down a few styles.

How to Wear 

(1).  Chukkas 

Let’s start with popular men’s chukka boots, shall we? Originally worn by British soldiers, during world war II, the pair is a simple style of men’s footwear.  Although they can be made from many materials, most of them are usually made from suede or calfskin.

They were first adopted as casual wear in the late 1940s to 1960s. They have since then continued to become a vital shoe staple in every man’s cool-weather closet. In terms of styling, they pair well with sport coats, cargo pants, and blazers.

(2). Leather Cap Toes 

This is any kind of footwear with horizontal stitching across the toe box.  The stitching extends to the welt on either side of the shoe, forming a straight-seamed cap.

As a more formal shoe staple, cap-toe ankle boots made from genuine leather can be dressed down with a good pair of striped pants, slim fit jeans, or a navy blazer. You can also choose to wear them with your winter suit and throw on an overcoat.

(3). Brogues 

These are low-heeled boots with decorative perforations. They come in an array of styles, colors, and materials like suede or patent leather. Your choice depends on your preference. Although termed an outdoor shoe not suitable for formal occasions, handmade leather brogue ankle boots can now be dressed down with simple closet regulars like vintage style t-shirts and ripped skinny jeans. Additionally, you can also choose to wear them with a two-piece suit or any other business attire.

(4). Wingtips 

Just like the normal wingtips, wingtip brogue ankle boots feature a pointed toe cap. This toe cap spreads to the sides of the shoes forming a design that resembles wings. With them reaching above the ankle, they are considered more casual wear than formal wear. The ones made from leather can be worn with pieces like split suits or casual pants like simple blue jeans.

(5). Two-Tone 

Quality handmade two-tone ankle boots are not only a perfect pair to upgrade your style but are also a bold shoe staple that is a must-have. Get yourself a pair, wear with fitting pants, and throw on a stylish men’s cardigan. You can also opt to dress them in a collared shirt, either polo or dress shirt.

(6). Leather made Jodhpurs 

Jodhpur boots for men are characterized by a non-slip sole with ridges. They can be worn in different ways. For those who want to create the impression of longer boots, consider wearing them with half chaps. Besides, they are a cheaper alternative to long riding boots. They can be worn with solid colored jackets and button-down cotton shirts.

(7). Chelsea Dress Boots

Chelsea boots are a very vital pair of shoes in a man’s closet. Made from high-quality materials, such as suede and leather, the pair can be purchased in black, brown, and tan, which are just a few examples. They look great when paired with regular closet staples like a double-breasted coat, a pair of black slim-fit jeans, or even knitted sweaters. If you want to wear them during summer, invest in a pair that has a rubber sole.

(8). Lace-up 

Stylish with any outfit, this pair features almond toes, an adjustable lacing system, and a padded insole that is a guarantee of comfort. The shoes can be dressed up or down to suit any occasion, from formal events to an everyday look. For a more casual look, wear them with relaxed fitting jeans.

 Tips for Wearing Lace Up Ankle Boots

  • Want to take a hike?  Although they are more casual wear, they can be useful in hikes and long walks. When hiking,  ensure that your laces are tied in a close-fitting manner. Tying your laces in a floppy manner not only makes your boots fit well but also causes less strain on your feet.

  •  For a relaxed look, keep your shoelaces loosely tied- If you want a more fashionable look, avoid tying your laces too tightly.

  •  For a pop of color, go for tall socks that will peak between your skinny pants and your ankle boots. This tip comes in handy especially if you want to give your brown or black ankle dress boots the attention they deserve.

Was this information useful? Step up your footwear game with our collection of quality handmade men’s dress ankle boots. Not sure what kind to shop for? Scroll through our selection on RebelsMarket for picks based on price, color, size, and style. Order now to enjoy great deals on all our handcrafted footwear. Shop for men’s clothing and accessories too.




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