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The Five Best Pairs of Dress Sneakers for Men

Magnanni Men's Caden Fashion Sneaker

If you're of the firm opinion that you shouldn't have to compromise comfort for fashion, then you're in luck. After years spent dreaming of the time we can finally wear our sneakers to formal events, date nights, the office, and anywhere else we care to, our prayers have finally been answered. Wearing your sneakers to the office and business-type events is no longer frowned upon. No one's going to turn you away from a club for wearing them. Your girlfriend isn't going to roll her eyes and pretend she's with someone else. Dress sneakers are officially a 'thing' and if you haven't already, it's time to jump on board the bandwagon and get yourself a pair. But let's get one thing clear from the start. All this sneaker love doesn't mean you get to wear your old Chuck Taylors to the office and expect a welcome reception from your boss. Neither does it means your scruffy old gym shoes get a second life in your suit closet. Dress sneakers are smart. They're slick. They're Stylish with a capital S. Not all sneakers get to become dress sneakers. Yes, they're comfortable, and yes, they're versatile. Sure, you can pair them with jeans. You could even team them with shorts if you're so inclined. But equally, these are sneakers that can be worn with a tux. Confused? Don't be. To set you on the path to success, we've rounded up the five best pairs of dress sneakers on the market. Grab yourself one of these little gems, and you'll never be stuck over what to wear again.

Polo Ralph Lauren Vaughn Sneaker

1. Polo Ralph Lauren Vaughn Sneaker

To qualify as a dress sneaker, a sneaker needs to pass a few tests. It needs to display a minimalist design - in-your-face embellishments and all-over logo prints are a no-no. It should ideally have a low top design - high tops are great for casual wear, but teaming them with a suit takes a deft hand to pull off. It should have a design that's similar enough to a dress shoe to appear refined. Lastly, it needs to be made of a traditional, premium material like leather or suede. Mesh, canvas (except in a few circumstances), and anything synthetic are off the table. The Polo Ralph Lauren Vaughn ticks the boxes on all those requirements and more besides.....which may or may not explain why has chosen to honor the sneaker with a mention on their round-up of the best dress sneakers for men in 2020, not to mention why we've chosen to do the same. So, what's so special about them? For a start, there's the classic style, which is refined enough to partner a suit, but casual enough to work with jeans. Then, there's the unbeatable quality of the materials, which sees a viscose and wool upper partnered with some very stylish leather laces. Finally, there's the comfort that, thanks to the robust rubber sole, padded collar, and breathable lining, is without fault. If you want to invest in a pair of dress sneakers with an affordable price point, you'll struggle to find much better.

Cole Haan Men’s Grand Crosscourt II Sneaker

2. Cole Haan Men’s Grand Crosscourt II Sneaker

The Cole Haan Men’s Grand Crosscourt II sneaker has class to spare. With its classic, refined design, it's the perfect complement to suits, evening wear, and anything else you choose to pair it with. Crafted in the style of a sporty Oxford, it'll take you through any occasion with style. Best of all, it comes in a variety of options, from the all-white, all-leather version to a very stylish plaid pair. Thanks to Cole Haan’s “Grand O.S.” (i.e. the company's commitment to flexibility, lightness, and cushioning), your feet will feel just as good as they look.

Steve Madden Men’s Ringwald Fashion Sneaker

3. Steve Madden Men’s Ringwald Fashion Sneaker

Steve Madden might specialize in funky, chic sneakers that bridge the gap between high fashion and street sensibilities, but it also does a fine line in refined, classic sneakers that ooze class. Take the Ringwald as an example. Simple but never boring, refined but eye-catching, these are sneakers that will see you through any occasion with style. Available in a good selection of colorways (white, black, tan, navy, and red) and featuring a low-key, low top design that pairs as beautifully with suits as it does with jeans, the Ringwald is a gem of a shoe with a very attractive price point. If you're looking to dip your toes into the world of dress sneakers, you'll find few better ways of doing it than slipping your feet into these.

Lanvin Cap-Toe Suede and Patent-Leather Sneaker

4. Lanvin Cap-Toe Suede and Patent-Leather Sneaker

According to, the Lanvin Cap-Toe Suede and Patent-Leather Sneakers are the epitome of ‘business casual’ and ‘ideal for dipping your toe into the dress code-spanning world of sneakers.’ We wouldn't dream of disagreeing. Whether you dress them up or dress them down, they're going to look good. Based on a classic Plimsoll design, the sneakers feature soft, black suede uppers, matte-leather trims, and shiny patent leather toecaps. They're slick, they're comfortable, and while they might be expensive, they're more than worth the investment.

Magnanni Men's Caden Fashion Sneaker

5. Magnanni Men's Caden Fashion Sneaker

Described by as the Rolls Royce of dress sneakers, the Magnanni Men's Caden Fashion Sneaker has all the qualities of a first-rate sneaker. For those who're not aware of Magnanni, the quality of the sneakers might come as something of a pleasant surprise. For those already well versed in this Spanish company's history, it's par for the course. Magnanni has spent the past 50 years producing some of the finest quality men's footwear on the market. Their distinctive hand finishes and detailing elevate their elegant designs to something extraordinary. Their commitment to using only the finest leathers and materials, meanwhile, is worthy of applause, as is their ability to deliver exceptional comfort and flexibility with each shoe. The Caden follows in the fine tradition of every Magnanni shoe that came before it. Crafted from exquisitely soft leather, a durable rubber sole, and featuring a lace-up closure for an adjustable fit, they look and feel like a dream. It may be an ankle shoe, but on this occasion, we're willing to waive the low-top requirement of dress sneakers. It's one downfall is its excruciatingly high price tag. But considering these are sneakers that will see you through almost any occasion for years to come, they're more than worth it.

Garrett Parker

Written by Garrett Parker

Garrett by trade is a personal finance freelance writer and journalist. With over 10 years experience he's covered businesses, CEOs, and investments. However he does like to take on other topics involving some of his personal interests like automobiles, future technologies, and anything else that could change the world.

Read more posts by Garrett Parker

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