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Top 5 Stylish Watches Under $500

By Akil Wingate


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Fear not swanky dressers and style aficionados. Sure the economy is in the tank but that doesn’t mean your sense of style should be martyred because of it. In fact, if nothing else your knack for pairing the right timepiece with the right button down shouldn’t take a hit.

We’ve combed the lookbooks and boutiques, catalogs and salons to find the top five stylish men’s watches under $500 so you won’t have to. Salivating at the thought of upgrading your watch collection with a fistful of nice affordable timepieces? Have at it…

The Sea-Gull OEM Classic Rodina

The Sea-Gull Classic Rodina. Photo courtesy of Sea-Gull.


Never doubt the wise words of an older gentleman when he says elegance never goes out of style. And elegance isn’t necessarily a price tag but certainly is a comportment. Look no further than the Sea-Gull OEM Classic Rodina. Listing for a modest $179, here’s a simply understated timepiece clocking in at 39mm, with a sapphire crystal, a premium stainless steel case and polished leather strap.

The automatic movement is a Sea-Gull Automatic ST1701 and promises to last the lifetime of the wearer. When do you wear this one? Anytime you please. It’s simple presentation with the large dial and understated sense of pizzazz is on par with the sort of look you’ll want to cultivate going from the golf course to the boardroom, the boardroom to the weight room, the weight room to the bedroom. You get the point.  

The Skagen Hagen Connected Titanium and Leather Hybrid Smartwatch

The Skagen Hagen Titanium Leather Connected Hybrid. Photo courtesy of Skagen.


Skagen has been firmly planting roots in the soil of stellar watchmaking for some time now. It should come as no surprise that the brand has set its sights on forward thinking design. Such is the case with the super stylish connected watch the Hagen Connected Titanium and Leather Hybrid Smartwatch. Got all that in one gulp? The name alone says just what this timepiece is made of: brilliant elements.

The titanium case, soft leather strap and connected dial are just the tip of the iceberg. The watch features an activity tracker, wifi, synchronicity with music and connected devices, adjustable date and time, and allows the wearer to even snap a photo. How much does all that retail for? $215!

The Lacoste Montreal Black Leather Strap Watch

LaCoste Black Leather Strap Watch. Photo courtesy of Lacoste.


Lo and behold, upmarket brand Lacoste has rendered a timepiece for a modest price of $154. The Lacoste Montreal Black Leather Strap watch is exactly what it says it is. Again, the trend with stylish watches is understated and classic appearance. Such is the case here with Lacoste.

While other iterations of the same timepiece with a large white dial and classic numerals exist with the signature alligator green band, here comes the basic black version. Typical bells and whistles: stainless steel case and 3ATM. The Montreal is a viable contender for watch of all seasons. It curates all the best elements that Lacoste collects under the hood for its other timepieces, and rounds them up here on your wrist.

The Triwa Havana Nevil

The Triwa Havana Nevil. Photo courtesy of Triwa.


The Triwa Havana Nevil is Triwa’s stellar take on the classic chronograph, complete with tanned leather strap and a silver sunray dial. Clocking in at 42mm and a 10ATM, the Havana Nevil boasts a 10ATM. The look is simply polished and poised. Perfect for that afternoon horseback riding or rounding up the troops in the office.

But what is most impressive about such a beautiful piece is that it retails for only $265. It ticks in fluid choreography while using a quartz Miyota OS21 movement. Triwa is certainly a game changer when it comes to rendering elegant timepieces for affordable prices.

The Uniform Wares 251

The Uniform Wares 251 Series. Photo courtesy of Uniform Wares.


Here’s a timepiece that has taken up residency on a host of design lists for beautiful and elegant design. But don’t let that stop you from wanting to rock this timepiece on your wrist. Uniform Wares is adept at making sense of the intersection of design and functionality.

Here with the Uniform Wares 251 they accomplish a singular work of beauty so stylish you’ll do a double take when you realize it retails for under $500. The dial is a thing of wonder with its chamfered ring and wedge like hands. Brushed steel adds a nice nuance for the gentlemen who wish to wear this to any event they please. The straps come in a variation of colors: taupe, tan, black.

About Akil Wingate

Akil Wingate is an explorer, producer, filmmaker and writer based in Paris, France. When he isn't traipsing the globe he is usually whipping up a mean millefeuille stracciatella in the kitchen. Learn more about WYCA's Editorial Process.

1 thought on “Top 5 Stylish Watches Under $500”

  1. Hi Akil,
    That UNIFORM WARES 251 is absolutely beautiful. After reading this top 5 list article I have been looking online to buy one, but I just can’t find it anywhere! Can you please provide a link to where I can purchase one of these watches?

    Many thanks,


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