A Gentleman’s Guide to Tailoring for Watches

Tailoring has a million-dollar question—and a good reason to ask.

“On which side does sir dress?” 

Generations of Savile Row tailors have asked this brilliantly tactful question. The proper answer is a simple “left” or “right.” The expert tailor would then add to his measurement at the top of one trouser leg in order to leave some extra room for a gentleman’s gentlemanliness. Custom tailoring is a world of tradition, sometimes subtle and unspoken, sometimes less so.

Tailoring To Bulk: Your Watch or Otherwise

The tailor’s art is one of taking that crudest of materials—man’s body—and clothing it in a way that, at the very least, covers up some of its natural horrors. A large part of the achievement is balance and harmony in the silhouette of a suit.

Natty’s Secrets: A Very Incomplete List

  1. Tricks of The Eye. An angled shoulder or one trouser leg longer than the other to account for lopsidedness
  2. Concealment of Bulky Areas. And one of the bulkiest for a modern gentleman is his watch (ahem).  
  3. OCD Dandyism. I match my socks to my undergarments.

A Tailor’s FAQs

Men sometimes forget to wear their watches when I’m measuring them, so I’m always sure to ask if they wear one and, if so, on which wrist. If they only wear a watch sometimes, I’ll ask how likely they are to wear it with the particular suit or shirt. If a beautiful watch factors into the ensemble, I’ll add between an inch and an inch and a half to the shirt-cuff or jacket-wrist measurement.

Of course, it always helps to have the watch present to take a measurement of the client’s wrist with and without it.

I have one friend and sometime-client who insists on being measured fully suited with his watch on and all of his usual accessories in his pockets, so his pattern reflects what he carries with him. A more traditional tailor would likely insist his client be in undershirt, boxer shorts, and stockinged feet for the fitting. He would calculate the necessary additional measurements for a watch after the fact. Or he would build the suit large for the first fitting and cut it down with subsequent fittings, like a master sculptor cutting away at marble. Luckily for my friend, I’m not a traditional tailor.

A watch isn’t the only item we can accommodate with expert tailoring. A detective might need room under one arm for a shoulder holster. A magician might need a secret pocket in the back lining for handcuff keys. But more of my clients wear watches than carry handcuff keys. At least that I know about. 

Ideals and Aspirations: Try Some of These at Home

DO: The ideal is a shirt and jacket cuff that leave room for the watch to just peek out when not in use and be fully exposed to read with an easy flick of the arm.

DON’T: Avoid the awkwardness of a too-tight shirt cuff catching under the watch’s case. This can lead to all sorts of sartorial nightmares—bunching up the sleeve, destroying the line of French cuffs, mangling a perfect, stiff starch. 

AT YOUR OWN RISK, BUT RAKISH AF: Gianni Agnelli, the former president of Fiat motorcars and a legendary dandy in his time, famously wore his luxury watches over the left cuff of bespoke shirts. This is a tricky technique, mastered by advanced dressers only, perhaps carefully practiced by mere mortals.