My S works in a business casual environment but I gave him (and all his buddies) monogrammed cuff links for HS graduation. They’ve all been wearing them to the weddings that have seemed to come every weekend this fall and winter. I agree about tie tacks, but a nice pair of cuff links can come in handy occasionally.
@alwaysamom Would you believe he is in the middle of his junior year of college and has a beard?!
Me neither. However, my son does wear cuff links - that musician thing. He wears a bespoke tuxedo and cuff links. I got him a lovely pair when he played the music for his sister’s wedding last week. I know he would never wear them if he weren’t playing.
No, he’ll wear his honkin’ West Point class ring for life. (They get two: a jeweled one for dress and a granite “battle” ring for everyday). It’s a thing. He did not get a HS ring. He likes French cuff shirts, so we got him cuff links with his HS crest for HS graduation and a set with the WP crest this Christmas which he wore to a NYE party. So, he does wear jewelry but has no interest in a non-computer watch.
Bingo. This.
-Agent 99-
A Roth is a great idea IF he is working (or you own your own business and can have him do your computer work or something and pay him, then convert it to a Roth. We did that for our s’s in HS.) But we also gifted kids stock and they always appreciated it.
I heard the same rumor that young(er) people don’t wear watches anymore, and use smartphones. I was pleasantly surprised when DS loved the Fossil (leather band) as a gift and he wears it often. If I were you, I would not spend a lot of money, perhaps buy somewhere like Costco with a generous return policy, just in case.
Another option for a HS boy, is a nice blazer or suit, which will get a lot of use in college.
What about using the money to open him his own brokerage account?
I’m more of a watch “accumulator” than a collector. I have several. My sons(18 &15) have already picked one of my dress watches that they would like me to gift them eventually. The 18 year old wears an indestructible G-Shock every day. The 15 year old doesn’t wear a watch at all.
A “dress” watch should be part of every man’s wardrobe. I’m partial to the traditional style with a leather strap that matches my belt and shoes, but a watch with a bracelet can be dressed up or down more easily and brings most sport/dive watches into play.
Tie pins have resurfaced the past few years among the younger, fashion-conscious crowd. It’s kind of a throwback look.
https://www.gq.com/gallery/best-tie-bars-to-wear-with-any-suit-and-tie
And in certain circles, cufflinks are a thing - preppy crowd, Wall Street crowd.
I third/fourth the idea of an investment account - Roth or not - perhaps combined with an intro book on investing. Never too early to get them interested, IMO.
Wow, some of those are quite pricey, @doschicos. I bet if I wrapped a brand new large, shiny paperclip in a nice box, our son might think that was a cool clip.
Our 20 year-old spends 99% of his time in sweats and tee shirts and wearing a cheap rubber watch, but likes to put on the dog occasionally. He has an Armani watch (not that expensive, especially at the outlet) that he wears when he puts on a suit. His older brother, who also wears a watch most of the time for work, gave him a smart watch that links with his new phone.
If we gave them cufflinks we would also have to give them a French cuff shirt. Neither boy has made the leap. Neither owns a tie tack.
I find a lot of the younger generation is not interested in accumulating “stuff.”
Son likes cuff links also.
Watches are like artwork and religion. You’re either into them or your not, and if you are, your taste for/in them and their variations is very personal.
I would not buy him a watch unless you know he is open to having one, and as much as I’m sure you’d prefer to pick it out and surprise him, I’d consider letting him pick out out because it is such a personal thing that he may have for a long time to come.
I know it’s difficult to buy for sons who tell you they really don’t want/need anything, but I’ll offer a method for getting ideas from them that worked on me over the years. There were some variations, but you’ll get the idea.
“Son, I know you’ve told me you can’t think of anything you want or need as a gift, but I want to get you something for this milestone and I can’t rest until I do. I would love for it to be some kind of meaningful keepsake, like a nice watch, but if a watch is something you are sure you’d never use, I’ll settle for something you might use for a few years. It doesn’t need to be anything practical or something you need. Sometimes it’s fun to get something totally impractical that you’d be reluctant to buy for yourself. So would you please] help me out here? It would make me soooo happy. Otherwise, someday when I’m physically gone from this earth, I’ll follow you around and haunt you every day for the rest of your life.” 
I got married young (age 24) and received a nice luggage set that has been one of my favorite gifts of all time. I think this could be a nice idea for an 18 year old who will be flying the nest and starting new adventures soon, if he doesn’t have his own luggage already. Not a keepsake, but a larger “lifetime” or at least many years kind of gift…if you decide that a watch won’t go over (hard to know, times have changed!)
Briggs and Riley carry-on bags have the best lifetime warranty and are set up to carry suits if he is likely to travel. It may outlast a watch. It will definitely cost more.
Depends on the watch. 
Watch can/will cost more. FSIL has a watch collection. He has his eye on one that costs mid-4 figures…has to get through med school/residency first.
Sometimes Briggs & Riley luggage are at Costco. We bought a 2-wheeled model that fits in most overhead bins for $139 (normally $400). It has been an excellent piece and we have no regrets.
There is something to be said for tradition and sentimental value so a watch or a necklace as a jewelry piece will always be valued even if it is not worn often.
I received a watch on my graduation which I didn’t appreciate until several years later and then it was one of the few pieces I wore constantly. Sometimes the value is in the love.
Some people don’t realize how much some watches cost. I have an acquaintance that wears a $39,000 watch. You’d be surprised by what some people wear.
I think the OP needs to decide…is this a gift he wants to see the kid use all the time…or is this a keepsake?
If a keepsake, a nice watch is a nice gift.
If the OP wants a gift the 18 year old will use a lot…a watch might not be the best choice.