The Art of Pairing: Matching Rolex Watches with Your Personal Style

by Rosemarie Hardison
matching rolex watches with your personal style

The terms ‘style’ and ‘fashion’ are often interchanged, but in truth, they are completely different concepts – a simple truth that could revolutionize your own approach to your wardrobe. Fashion describes the movement of trends and the trending status of specific items and fits; style, meanwhile, has altogether more substance, and a timelessness to boot.

Speaking of time, this is how well-regarded watch brands can endure through generations. Rolexes are symbols of status and wealth to some, but they are also highly effective style signifiers. Knowing how to wear a Rolex, though, is a new challenge for many. What should you consider when matching a prospective watch purchase to your sense of style?

Rolex – A Diverse Brand

The Rolex name is a household one, and for very good reason. It has cornered the market on watches, with distinctive yet wide-ranging watch and chronograph designs that run the gamut of analog watch trends. There is a collection for every occasion, and a Rolex for every style.

One of the more beautiful aspects of Rolex as a watch brand isn’t its breadth or style or attention to detail, impressive and valuable as they are; rather, it is the timelessness of Rolex as a brand, which informs the value of each timepiece now and in the future. Older Rolexes retain both their financial and cultural value, going so far as to be a useful store of value amongst other assets. But here, we’re concerned with how to wear them. Speaking of which, how do you wear a Rolex?

Identifying Your Style

The first step in this process is to reckon with your personal sense of style, and understand exactly what it is that you gravitate towards with regard to fashion. This is an excellent excuse to audit your wardrobe, and figure out exactly what works and what doesn’t.

In doing this, you’ll find some common threads across your chosen outfits, while maybe also identifying some gaps in your collection. As you go through your clothes, keep asking questions: do I lean towards a sporty, adventurous look, or do I prefer smarter fits? Am I a colorful dresser, or do I seek sharp monochrome elegance? Answering these questions will get you closer to your sense of style – and give you baselines from which to fit your watch collection.

Classic Elegance

Rolex watches are most commonly attributed to the smart, elegant folk amongst us. Quintessential watch designs like Oyster Perpetual positively shine against the defined lines of a tailored suit, particularly if it’s black. The brushed gunmetal finish is classic without being ostentatious, and gives just the right hint of glimmer.

Sporty, Casual Vibes

Rolex watches are not all formal elegance, though. There are classic styles designed for casual wear, and even for sport; look no further than the Submariner or the Yachtmaster for a simple, polo-friendly style and vibe.

Vintage Charisma

For the nostalgia-freaks amongst us, 70s style is not going anywhere. High-waisted corduroy and tight shirts play well with older Rolex designs, as well as modern throwback examples like the 1908 or Sky-Dweller.

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