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The Everyman’s Guide To Picking The Perfect Wristwatch For Every Occasion

Take time out to fixate on the details
by Shayne Exito | Nov 5, 2016
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Out of all the accessories men dare to wear, the wristwatch is the one that seems to inspire the most investment and attention. Perhaps it’s because your watch says a lot about the type of man you are. And no, we’re not just talking about the pricetag. The wristwatch, as something that perfectly combines style and function, is a subtle detail that shows the amount of care you put into how you present yourself to the world.

A rocking wristwatch can take your look from so-so to effortlessly dashing and debonair. A badly matched watch, though, can ruin your otherwise solid getup. It’s an accessory that can make or break your entire outfit, and the key to nailing the perfect combination is paying attention to the details—the material of the strap, the face, and even the color of your timepiece.

If you think that’s a lot to consider before stepping out, don’t worry, we’ve got your back. We asked professional stylist (and FHM favorite) Debra Bernales to give us a breakdown of the simple styling guidelines you need to keep in mind when picking out a watch for specific occasions.

On Color Matching

As a general rule, remember that the wristwatch is an accessory, and should match with your bag, belt, or shoes.

“The easiest way is to always match the color of your strap to your shoes,” Bernales says, adding that you don’t have to match tone to tone, and instead encourages making your color combinations complement each other.

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So when you’re sporting a silver watch, wear it with shoes in blue or black hues. Gold watches, on the other hand, should be worn with tan oxfords or shoes in neutral earth tones.

Watches with leather straps fall under the rule of thumb used for all leather accessories: “Brown must go with brown, black must go with black.”

Of course, your shoes, as well as your outfit in entirety, depends on the occasion, such as:

Formal Events

Those times you’re expected to dress to the nines in your classiest suit and tie, you can’t just strap on your regular ol’ sports watch and go on your merry way. This will completely ruin your look and totally erase the sophisticated and elegant image you were trying to pull off.

Instead, always go for the the dress watch, which is typically a thin, analog watch with a leather band, that should easily slip under your cuff. Bulkier watches are to be avoided at all costs since they can ruin the line of your jacket at the wrist. 

The casing, which may be rectangular, circular or square, must match the other metal trimming you’re wearing. “Try to check your cufflinks, tie clip, or the buckles of your waistcoat, as all metals must go together,” Bernales says.


You can also just completely do away with the problem of matching your watch to you outfit by breaking out your lolo’s pocketwatch. This luxurious accessory will surely give you classier vibes; just be prepared for the inconvenience of always having to pick it out of your pocket just to check the time (though we’re sure you’re used to doing that with your phone, anyway).

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Business Days and Date Nights

Many companies nowadays no longer require—and in fact may even discourage—corporate attire. The hoodie and t-shirt look has become the new uniform for many professionals. For this article though, let’s assume your business look, while on a sliding scale of casual to formal, still mostly consists of the classic button-down shirt, chinos/slacks, and brogues/patent leather shoes, with the optional jacket and tie should the AC allow it.

Your date night style game would incorporate more or less the same pieces, probably only switching out an item or two to make you look less stuffy and more charmingly approachable.

Either situation though, you’ll be attempting to dress smartly, and the best way to finish the look is always with a high-end chrono wristwatch with either a rubber or metal strap, Bernales tells us.

For business and business casual looks though, the latter is more often the better choice.

Chrono and dress watches with leather straps can also be worn for work or dates if you want to look really sharp, though just avoid them if you’re only wearing a t-shirt and jeans with your blazer. Bernales reminds that like always, “leather complements leather,” so match your watch to your shoes and belt.

Watches worn to business and casual events are typically medium to large in size, which is bigger than the regular dress watch. For all instances though, make sure that the width of the band and size of  the watch face are proportional to your wrist.

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Casual Affairs

Your style should match your personality and lifestyle, and your specific outfits to the activities you’re about to attend. So for those gimmicks and high energy events you’re always going to, pick a watch that will not only stay on for the entire performance, but also fit in well with the rest of your casual/sports wear.

For outdoor activities like going for a run or biking, or for when you’ll be sporting athletic gear in general, Bernales suggests you choose chronos or sports watches with rubber straps to complete your t-shirt and shorts looks.

Watches with canvas straps can give you a more rugged appeal. You can also play with more dynamic and fashionable watches with plastic bands in a variety of colors. “If you want versatility, pick a watch with interchangeable bands, that way, you’ll splurge [only] once on a watch that you can pair with more outfits,” Bernales advices.

She also adds that for those with more active lifestyles, digital might be a better choice over analog watches.

Unless you’re a collector, you’ll only really need to buy a few kinds of watches to be ready for every occasion thrown your way. Though if you want your watch to last, possibly even for a lifetime, don’t get the cheap knock-offs being sold on the side of the road and instead invest in quality watches. You might be able to pass them on to your kids someday. 

For more professional styling advice, you may reach Debra Bernales via email at or Instagram. You can also visit her website here.

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