Watches and Style: Ann and Sid Tackle Common Questions

Watches, like clothing, are varied in sizes, colors, styles, materials, and a myriad of other accents and factors that make each piece unique. Here, on Unwound, we often talk about the mechanics, history, and design of watches themselves, but we don’t often touch on style.

So, we turned to our friends and style experts Ann and Sid Mashburn to help us answer some often-asked watch style queries.

Ann and Sid, founders of their namesake stores, have long been a staple in the world of fashion and style. They create classic clothes, with great stories and some surprises mixed in. They have a studied perspective on clothes and fashion, making them the perfect pair to answer these common watch questions.


Do you match your watch to your clothes?

Sid: Absolutely, but maybe not in the typical definition of the word “match.” I think of watches as a bit of a style lever that you can dial up, or down, based on the rest of your ensemble. Need to add an elegant lift to a casual outfit? Go with your nicer watch. Wearing a bold jacket or maybe some colorful, patterned pants? Now’s not the time for the statement watch. Instead, balance that flash with an understated timepiece. I always think about the outfit as a whole, and which watch compliments it.

Ann: Kind of, not to match per se, but style. Though sometimes the style, if it contradicts what else you are wearing, can look great as well. For example, a little black dress with minimal jewelry for the evening but with a large, masculine Rolex would be great. 

Can you wear watches and bracelets together?

Ann: Absolutely. But I guess it depends on the style of bracelets. I would say the clanking of metal bangles is probably a no, but I love the mixture of a watch with many bracelets – very chic.

What is the right watch size for your wrist?

Sid: Every guy is different, but my sweet spot is 35-39 – which is mostly based on my wrist size. Though there are always rooms for exceptions – I chose an IWC Portuguese for our Crown & Caliber collection, and that comes in at 41.

Ann: I like many sizes for the same reason as matching watches to clothes. Style. Sometimes I like a chunky watch in the same way I like a chunky bracelet. Other times I want something simple and delicate. For me, it’s like jewelry – I love lots of different styles and sizes.

Can I wear a sport watch with a suit?

 Sid: I’m a big fan of high-low combinations, and there are ways to pull this off. One rule of thumb is let the size be your guide – the thinner the watch, the easier it is to wear with a jacket. And if you’re already wearing a suit – let your watch be discreet.

How do you wear a blue-faced watch?

Sid: Just like any other watch. With confidence.

 How many watches should a guy own?

Sid: It’s nice to have an everyday watch that can go anywhere, and with anything. For me, that’s my Rolex Explorer 1016, but for guys in our office that might be a Timex. And after that I would focus on adding a watch or two that you find interesting. Maybe it’s a red tipped sweep hand or a calendar or a chronograph or maybe it was made in the year you were born. But just something that personally appeals to you. Plus, it’s fun to have a few watches in rotation to call up from off the bench.

What watch do you wear to a wedding?

Ann: I love a metal watch for the evening. The Cartier Ballon Bleu with its mix of silver and gold comes to mind. It’s a great watch, but it really depends on the style of your dress. And if it’s for your own wedding…NO! On that day, time needs to stand still!!!

What watch should I wear with a tuxedo?

 Sid: You’re in a tuxedo, which is basically a uniform to make you look good – most every man does – don’t overcomplicate it. If you’ve got a thin, simple, elegant watch – by all means, wear it. And if you don’t, it’s perfectly fine to NOT wear a watch at all. Hopefully it’s the type of party where you’re doing more dancing, and less checking the time.

How do you choose a watch for a woman?

 Ann: It doesn’t matter if you are a friend or a lover – you cannot buy a someone a watch (it’s a big deal!) without putting in the time to be fairly sure you know them. You will find your way just by being curious and noticing her loves and interests! And hey, if you make a mistake – you can always go back and say “wow, how wonderful that you are still a mystery to me! There is so much more I want to know about you.”

Watches are deeply personal. Their styling, mechanics, and wrist presence vary by watch and the preference varies by person. Hopefully this insight from two of fashion’s finest, in Ann and Sid, helps guide you to not only loving a watch that suits you, but also keeping it stylish.



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