When it comes to dressing for a night at the casino, the dapper dudes understand that it’s not just about luck—it’s about making a stylish statement. And that includes your shoes! Don’t just wear any old pair you have around; elevate your look with gorgeous leather shoes.
Leather is timeless in appeal and versatile in style, plus it’s built to last. There is a range of options to suit various casino settings and personal styles, so if you’re dressing to impress or going for a more casual look, leather shoes are still for you.
Here are some of the best men’s leather footwear options to put your best foot forward during your next night cruising the casinos.
Oxford & Derby Shoes
Oxford and derby shoes are very similar in appearance and both well suited for formal wear. They are timeless classics in men’s footwear and endure in popularity because of their versatility. Oxfords and derbies are elegant and the perfect choice for fancy occasions.
Oxfords sport a closed lacing system, which imparts a clean and minimalist design. These shoes fit well at black-tie events and are considered sleek and refined. Oxfords go especially well with nicely tailored suits.
Derbies have an open lacing system with visible flaps, but the differences between the two styles are minimal. Derbies have a bit more flexibility in terms of fit and may be better for semi-formal occasions where you don’t want to appear overdressed. Derbies go great with business wear, blazers, button-downs, and dress trousers. These can be good for a night when you know you’ll be taking off your suit jacket and loosening your tie!
London-based brand Oliver Sweeney keeps the British tradition of these shoes alive with beautifully handcrafted pairs that are sure to last long after your night of gambling is over.
Loafers & Leather Sneakers
Loafers or leather sneakers are a great go-to for style and comfort. Loafers are slip-on shoes with low heels that offer a relaxed yet polished appearance. Choose from classic penny loafers or go more contemporary with tassel or horsebit loafers. These shoes are appropriate with dress trousers, chinos, or well-fitted denim.
Although leather sneakers are a bit more casual, there are luxury brands that elevate this typically humble footwear. Leather sneakers provide comfort and street style for smart-casual events. If you decide to invest in a pair, they go far beyond the casino.
Lace up your leather sneakers for date night, after-work happy hours, and other easy-going events where you still want to strike a chord with your appearance. Leather sneakers go well with slacks, khakis, and denim that complement the colorway of the shoe.
Enjoy adaptability and ease of wear when you rock a pair of loafers or leather sneakers. They are both suitable choices for more casual environments but can also be dressed up with the right ensemble!
Cowboy Boots
Howdy, pardner. Cowboy boots might not immediately come to mind when you think of a night out on the town, but these puppies are a fun option if you’re up for trying something new or dressing on a theme. Set yourself apart from the usual casino crowd when you rock your best western wear.
Cowboy boots go well with jeans, statement belts, modest button-down shirts (no tie, unless it’s a bolo!), and hats—baseball caps or even a ten-gallon if you want to go all-out.
Whether you’re visiting Vegas or casinos in the American Southwest, there are plenty of western wear stores you can shop at for the authentic experience. These stores will have everything from work boots to exotic options crafted from snakeskin and even alligator. Be sure to break your boots in before you wear them out—or else your dogs will be barking!
Express your style with flair and start up a conversation when you choose from the almost endless styles of cowboy boots out there. You’re just as unique as your footwear, so show that personality off. Yee-haw!
Chelsea & Other Boots
Chelsea boots, chukkas, and Timberlands are three distinct leather footwear options for your night out. They each have their own charm and style, but they are all suited well for polished yet casual occasions.
Chelsea boots end at ankle height and have a slim profile that goes well with slim or skinny jeans. Chelsea boots are trendy, easy to wear, and come in a variety of soles that will set you apart from the average gambler.
While chukkas are also ankle-high, they sport laces instead of a pull-on style with a tab like Chelsea boots. These are a little more on the casual end but can be dressed up with a blazer. If you buy a pair of chukkas that you love, consider wearing them to your next concert, an art gallery, or a nice restaurant. You’ll fit right in.
Timberlands are more of a statement, but the right person can pull them off with aplomb. They have rugged charm and street cred aplenty. They’re also practical, so you can repurpose them as work or commute shoes when you no longer want to save them for nights on the town. Timbs go best with tucked-in or cropped jeans and a more casual top. They’re synonymous with adventure and are comfortable to boot—a perfect pick for your next long night out!