The Best Oxford Shoes to Bring Timeless Style to a Variety of Looks

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There are many types of footwear men can choose, but the best Oxford shoes remain timelessly stylish.

Why are the best Oxford shoes so effortlessly fashionable year after year? There are several answers to that question. And it depends on what you love best about this style. There is the fact that they can be far more comfortable than some more formal footwear. Then you can consider the wide variety of styles and fabrics available to suit any occasion. Finally, finding that perfect middle ground between casual and dressy can be just the thing to bring a look together.

The fact that it is so universally loved for so many reasons explains its longevity. Chances are, you know guys from multiple generations who rotate the best Oxford shoes into their wardrobe. And it can accentuate the best in all types of outfits. Of course, just like anything else, there are different levels to the quality and style available. So keep reading to determine what some of the finest example of this footwear can provide to your look.

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The Best Oxford Shoes for Men of All Tastes

If you’re looking for a pair of shoes for a wide variety of uses, you might need some great Oxfords. But despite a somewhat similar design, this is a wide and diverse segment of men’s footwear. So we will navigate the marketplace to allow you a glimpse at the styles and fashions available. Whatever you need in a pair of the best Oxford shoes is probably on display somewhere on our list.

1. Anthony Veer Roosevelt Men’s Monk Strap Dress Shoe

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The distinct strap is a more unique take on the design. Some guys find it more stylish and you might want to mix up your footwear game with this look. If it catches your eye, chances are you’ll be hooked when you try it on. Tons of positive reviews describe these as comfortable shoes to wear for hours at a time. So whether you’re dressing for a night out or just a day at work, you should be in for a pain free experience.

Find some of the highest quality leather stitched together with expert precision. And one of the most enjoyable qualities is its ability to fit to your foot over time. The longer you wear them, the closer it molds to the perfect fit. And you can wear these for a good long time as it gets broken in to become one of your favorite pairs. Even the supportive insole is wrapped in luxurious leather. These are well made and stylish shoes for a variety of uses. Dress up a nice pair of jeans or keep a dinner jacket casual. Either way, these could be the best Oxford shoes for your next event.

2. Florsheim Men’s Medfield Cap Toe Oxford Dress Shoe

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Here’s a timeless style that represents about the best Oxford shoes available in this pattern. Enjoy the comfort of imported leather with a resilient and forgiving sole made of synthetic materials. The rubber gives you plenty of give as you are able to flex as much as needed to stay limber.

Plus, there are materials woven into the interior to help sweat evaporate. Keep your feet cool and resting on a supportive insole as you keep your look classic and stylish. A removable cushion for the soles of your feet gives you extra comfort as you walk around. And other features included in the design keep the shoes stable even with maximum wear and tear. So they might look like dressy shoes, but you can treat them like everyday kicks without worry.

3. Rockport Men’s Style Leader 2 Bike Toe Oxford

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Chances are you’ve heard of Rockport even if you’ve never owned a pair. The company has changed quite a bit over the years. But one focus has always been a comfortable design. And that’s exactly what you’ll get with some of the best Oxford shoes the company currently offers. 

Like many other top tier options, it’s got a leather upper and rubber down below on the sole. But this one has got some tricks under the very attractive surface. The classic lines and shape of theses shoes belie the performance shock absorbers underneath. Adidas helps provide this great feature to keep your feet stable under any circumstance. And the whole package is waterproof, so you don’t have to be too careful in watching the forecasts. The design is even meant to keep water off of your feet when you wear them in the rain. 

4. Chamaripa Men’s Oxford Leather Height Increasing Elevator Shoe

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Building on the traditional leather on top of a rubber sole, this style stands out for a very specific reason. If you’d like to subtly gain a bit of height, these would probably be the best Oxford shoes for the job. Of course, you can look sharp at any height. But for some occasions, maybe it’s better for pictures or some other reason to gain a bit.

Best of all, it’s all housed in a comfortable insole that conforms to the curves of your foot. And nobody will ever notice there’s a slight lift hidden inside the design. All they’ll see is a classic, simple look that accentuates almost any style. Plus, you can count on every material used in its construction to be the highest quality available. The resulting shoes are resistant to water and odors that will keep you comfortable in any environment.

5. Cole Haan Men’s Williams Wing Ii Oxford

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Cole Haan has a long history of creating fine men’s footwear. So it should come as no surprise that it also creates among the best Oxford shoes on the market. These are perhaps the epitome of the style. Crafted in traditional design but with the utmost care and attention to detail. There is leather everywhere, stitched to perfection for comfort and long lasting wear. 

This shoe has classic and elegant lines that will elevate the look of ordinary shoes in the class. The design cues are ageless while serving as a nod to the expert abilities of the finest designers. If you’ve worn Cole Haan before, you understand its definition of fashion and elegance. And if you haven’t, these fine shoes are a worthy introduction. Either way, they probably deserve a spot near the front of your closet.

6. Anthony Veer Men’s Regan Wingtip Oxford

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Crave leather everywhere? This one might be about as close as you can get. For starters, it’s got a fully leather formed upper as you might expect. But then there is a leather sole and an insole that’s also wrapped in leather. The construction is top notch and cinches closed with waxed shoelaces for a polished look.

If you like the look, feel and even smell of a perfect pair of wingtips or dress shoes, this will evoke great memories. But they are also made to last and with a design that is comfortable to wear. It’s the best of classic design mixed with today’s protective and supportive craftsmanship. Like any fine shoe, it will conform to the shape and size of your foot, giving you a perfect fit. Be warned, however, that you will want to order a size larger than your own. 

7. Red Wing Heritage Men’s Weekender Oxford Work Shoe

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You might think the best Oxford shoes are limited to dressy shoes. But the design itself can successfully be replicated in a much more casual style. This weekender style shows a familiar pattern in a lightweight and durable construction. All materials combine for an easy care pair of shoes to add some fashion to even laid back styles.

Few of us want to be formal every day. And you probably already know the best Oxford shoes look great with a perfect suit. They also work well with a pair of slacks and a nice shirt. But with a pair like these, you can stretch further the type of clothing you wear them with. Not only are they easy to pair with about anything in your wardrobe, they’re also easy to keep clean. Just use a soft brush with some water to loosen up stubborn grime. You can then use a dry cloth to finish up the job and go out looking dapper and stylish. 

8. Lethato Wingtip Oxford Goodyear Welted Formal Handmade Leather Dress Shoes

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Incredibly luxurious calfskin makes up the leather upper for these handcrafted shoes. Additional leather is included in the lining, laces and sole. It is all constructed to last and manufactured with the finest quality materials available. 

Cushioning in the sole comes from a custom production process that originates in Argentina. And it provides a consistently supportive and soft feeling that will allow you to wear them all day. Plus, you can go out confidently regardless of the weather. Not only will your feet stay comfortable and dry, water won’t damage the great looking exterior. 

Choosing the best Oxford shoes for your style can really expand your wardrobe. 

Put together new looks or recreate old ones with a new sense of style and functionality. This style hasn’t changed much over the years. But designers still find ways to keep them thoroughly modern and comfortable. Whether you want to go casual or keep things dressy, Oxfords can be your best bet.

And we hope our guide has helped you navigate the possibilities available right now. If so, share this article with the fashionable guys in your life. And leave us a comment below if you have any final thoughts or questions.

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