Anonymous
Post 11/19/2025 10:01     Subject: Older teen boy clothing ideas - dressy
DS is 19 and generally hates wearing anything beyond athleisure.

He's bought clothes from J Crew - generally will go with some sort of tech fabric chino, nice t-shirt under a quarter zip or a button down.

He has a couple of pairs of more casual dress shoes that have been picked up over time.
Anonymous
Post 11/19/2025 10:00     Subject: Older teen boy clothing ideas - dressy
Anonymous wrote:Quarter zips are in – big time. Of course they can be over a nice shirt or a button up shirt. As for pants, you can look at Hollister, Macy’s, Abercrombie.


this this this
Anonymous
Post 11/19/2025 09:19     Subject: Older teen boy clothing ideas - dressy
Sweater polos are another idea.
Anonymous
Post 11/19/2025 08:10     Subject: Older teen boy clothing ideas - dressy
H&M
Anonymous
Post 11/17/2025 18:08     Subject: Older teen boy clothing ideas - dressy
Anonymous wrote:Khaki/golf type/chino pants (not black unless you want him to look like he works at the movie theater) and a quarter zip. This isn’t hard, can’t your husband figure this out?

+1
No black unless they want to look like a waiter or in the band. Someone also suggested linen button downs and lands end/ll bean. No to all. Khaki pants, tech fiber or not, button down and navy blazer or quarter zip. Other option is a suit w/ a button down and belt but no tie.
Anonymous
Post 11/17/2025 17:55     Subject: Older teen boy clothing ideas - dressy
Khaki/golf type/chino pants (not black unless you want him to look like he works at the movie theater) and a quarter zip. This isn’t hard, can’t your husband figure this out?
Anonymous
Post 11/17/2025 12:25     Subject: Older teen boy clothing ideas - dressy
Anonymous wrote:
Anonymous wrote:I think a nice pair of khaki and black slacks will go a long way to starting this look.

Agree with pp who suggested a sweater. I would go lightweight Marino wool — something from Banana Republic, maybe. Cashmere blends are having a moment too … look in department stores and like Quince or Nordstrom Rack/Saks Off Fifth. Agree these can be dressed up with a collared shirt or tee for a more casual look. A blazer (get it tailored) can complete the outfit.

Also, don’t laugh but check Costco. More often than not they have good basics from brand names.

Finally, invest in a couple of pairs of shoes. Leather sneakers have been popular, although I personally dislike the look. Can’t go wrong with a decent pair of black chukka boots. Be sure the belt matches the shoes.



There’s no way you have a teen right now.


NP here and not sure why you say this. My late teens son wears khakis with a cashmere blend crewneck sweater and leather sneakers (nike killshots) when he wants to look nicer.
Anonymous
Post 11/16/2025 22:08     Subject: Older teen boy clothing ideas - dressy
Anonymous wrote:
Anonymous wrote:What are you talking about? Suits? Sports coats? Biz casual?


OP here. On the business casual side with a sweater look.


J Press. Take a trip to New Haven on a college visit to yale and get outfitted at the j press shop.
Anonymous
Post 11/16/2025 20:39     Subject: Older teen boy clothing ideas - dressy
Agree not for all. They are for the same guy who likes Blundstones (iykyk), but needs a sharper, major stylish boot for urban, stylish occasions.

https://www.nytimes.com/wirecutter/reviews/rm-williams-chelsea-boots-review/
Anonymous
Post 11/16/2025 08:41     Subject: Older teen boy clothing ideas - dressy
Anonymous wrote:My son loves the stretch chino style trousers from J Crew and Lulu (the latter has hard to find tall lengths). He prefers a slimmer cut, in a stone color or olive or navy. Anything but tan.

He borrows his Dad’s Paul Smith striped dress shirts bc we don’t want to spend like that while he is still growing.

And a cashmere 1/4 zip to look smart.

If his feet are done growing, you could splurge on a pair of RM Williams boots. It’s a quiet status symbol (that he will wear forever) among my older son’s friends.


I had to look up the RM Williams boots. I’m not seeing this around…they look like women’s boots. I would be hesitant to get these for my teen son unless he specifically asked for these.
Anonymous
Post 11/16/2025 08:18     Subject: Older teen boy clothing ideas - dressy
We have two teen boys and we attend synagogue weekly. Gap khaki pants. Find one that fits and get in a couple of colors. They have nice button-down shirts as well.

As PP said, add a sweater. Add a 1/4 zip. Depending on what the event are, either new sneakers or a pair of nice shoes.

They will adjust. It’s fine. It’s not a daily thing. It’s nice and respectful. Good luck!