A luxury watch often makes up the sum total of a man’s jewelry collection. So getting it just right at gifting time can come with real pressure. The decision often inspires fresh stress that goes beyond quotidian cost considerations.

For advice on how to commemorate the major moments in a man’s life through a timepiece’s personality, Alexa spoke with Myka Meier, founder of Beaumont Etiquette and author of “Modern Etiquette Made Easy: A Five-Step Method to Mastering Etiquette.” For authority on identifying the perfect prize, we chatted with Rebecca Ross, watch specialist at Christie’s New York, whose expert eye guides myriad celebratory wows.

Let their collective wisdom set you free from your what-to-get worry.

Graduation
Few gifts convey “all grown up” quite like a wristwatch. For a young man just entering the workforce, it’s best to keep it simple. Meier recommends selecting something “sensible and nothing flashy. You don’t want a nicer watch than your boss.”

The convocation watch is “likely the first that a young man will own. It represents achievement and relief,” says Ross. “A Tudor Heritage Black Bay signifies that school’s out and also shows you’ve done your homework. Steeped in history and credible in its field, the Black Bay pays homage to Tudor’s early dive watches from the mid-1950s and is more immediately useful than all those long exams.”

IWC Schaffhausen Blue Portugieser Chronograph in stainless steel, $7,600

Career Success
Being recognized for hard work and smarts through a promotion or new opportunities requires appreciation. Firsts only happen once, after all.

Ross advises that career turning points require a watch that shows the wearer can be boss (someday) while also exemplifying versatility.

“My choice is an IWC Portugieser Chronograph. The chronograph function acts as a stopwatch with a precision that can keep you on time to the nearest second, just like your manager on a Monday morning,” she says. “Plus, the classic’s details will hold up through several promotions.”

Meier adds that while you should seek out a special-occasion watch, you should also show some restraint. “Make sure it’s a tasteful splurge,” she says. “Anything too much may come across as bragging.”

Marriage
The wedding watch is the perennial favorite bride-to-groom goodie, although in-laws, too, often get in on nuptial gift giving. A smart guide is the watch’s legacy potential.

Meier proposes an “everyday watch that is also a keepsake to commemorate the big day — think a leather strap with a classic face.”

Ross agrees. “Fall in love with a vintage Patek Philippe Calatrava,” she says. “Elegant and sophisticated, a prospective heirloom you can pass down to future generations, and at a perfect size of 36 mm, it has a unisex aesthetic, so this is one of the many things in life he’ll be sharing with his wife.”

Breguet Classique watch in 18-k rose gold, $19,000

Retirement
For many men, saying goodbye to a lifetime of work creates conflict. On the one hand, hello hobbies and free time! On the other, hitting par on the back nine may not measure up to life’s previous wins. Our experts are also of two minds on the perennial present for retirement: Go big or go sophisticated.

Meier maintains that, “If you can dream of it, you should go for it!” The man who made it to this milestone “deserves all the bells and whistles,” she says.

Ross seeks a more practical side to indulgence and suggests something “refined and mature.” Retirement finally affords the “time to do all the nothing you want. Stop searching for those reading glasses; clean aesthetics and highly visible numerals will convince you your eyes are aging as well as a Breguet Classique.”

Want to make a real mark? Buy both.