The Art of Pairing Part I

In this guide, we explore how to select the perfect watch to match your attire and occasion, ensuring you’re always in sync with both style and purpose.
Written by Sanja Catenacci

A watch is more than just a timepiece—it’s a statement. The right watch can perfect an outfit, reinforce your personal style, and show that you understand the unspoken rules of sophistication. Whether you’re suiting up for a black-tie event or going for a casual weekend look, knowing which watch to wear (and when) is key. Here’s our guide to get it right.

1. The Black-Tie Affair: Keep It Classic

Outfit: Tuxedo or formal evening wear
Watch: Dress watch (slim, elegant, minimalist)

When wearing a tuxedo, simplicity is key. A classic dress watch with a slim case, a clean dial, and a leather strap is the only acceptable choice. Think of a Jaeger-LeCoultre Reverso, a Cartier Tank, or a Patek Philippe Calatrava—timeless icons that complement formalwear without stealing attention. Avoid chronographs, chunky cases, and metal bracelets; a formal event is not the time for sport-inspired pieces.

Tip: Black-tie events are all about elegance, so opt for a black leather strap to match your shoes and belt.

2. Business and Boardrooms: Understated Sophistication

Outfit: Suit (navy, charcoal, or grey)
Watch: Dress watch or luxury sports watch (steel or gold case, leather or metal strap)

A business setting calls for something refined yet authoritative. A Rolex Datejust, Omega Aqua Terra, or Vacheron Constantin Patrimony strikes the perfect balance between understated luxury and professional confidence. A steel bracelet adds a modern edge, while a leather strap keeps it traditional.

Avoid overly complicated dials—moon phases and perpetual calendars are great conversation starters but might be excessive for daily business wear. Stick to a simple three-hand watch or a subtle chronograph if you prefer a more technical aesthetic.

Tip: Match your watch’s metal with your cufflinks and belt buckle for a polished look.

3. Smart Casual: The Versatile Everyday Piece

Outfit: Blazer, chinos, dress shirt, or a fine-knit polo
Watch: Sporty yet refined (luxury sports watch, field watch, or GMT)

For a relaxed but sophisticated look, you need a watch that transitions effortlessly from work to dinner to weekend outings. A Tudor Black Bay 58, IWC Pilot’s Watch, or an Omega Speedmaster fits the bill. These watches have a strong presence on the wrist without being too formal.

This is where leather straps, NATO bands, or rubber options come into play, allowing for personal expression. A GMT or chronograph function adds practicality for frequent travelers or those who appreciate a touch of aviation history.

Tip: Brown leather straps pair well with navy and earth tones, while a steel bracelet is a go-to for versatility.

4. Weekend Casual: Effortless Cool

Outfit: T-shirt, jeans, sneakers, or casual knitwear
Watch: Field watch, dive watch, or digital (comfortable and rugged)

On the weekend, comfort takes priority. A Rolex Submariner, Seiko SKX007, or a Hamilton Khaki Field is a solid choice. Dive watches and field watches are built for durability and adventure, whether you’re heading to a café or a weekend getaway.

If you’re feeling bold, a G-Shock or an Apple Watch adds a modern, practical twist to your weekend look. These are perfect for the gym, running errands, or casual hangouts.

Tip: A rubber or NATO strap keeps things casual and functional, while a well-worn leather strap adds character.

5. The Sports and Adventure Watch: Built for Action

Outfit: Activewear, performance gear, or casual streetwear
Watch: Dive watch, pilot watch, or digital sports watch

For outdoor activities, choose a watch that can handle impact, water, and the elements. The Omega Seamaster, Breitling Superocean, or Casio G-Shock are rugged yet stylish options for adventures. If you’re into fitness tracking, a Garmin or Apple Watch Ultra keeps up with your pace.

Tip: Water resistance is key—make sure your watch can handle unexpected swims or rain.

Final Thoughts: The Watch Makes the Man

A well-chosen watch is a subtle but powerful detail that sets you apart. By understanding the right watch for each occasion, you show attention to detail and respect for style traditions. Whether you’re wearing a tuxedo or a t-shirt, there’s a perfect timepiece for the moment—choose wisely.

Picture of Sanja Catenacci

Sanja Catenacci

Editor

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