Anonymous wrote:Update from OP- Gap size 29 x 30 fit perfectly with a belt. Thanks so much for all of your advice!

Glad it worked out. I know when my son switch from boys to men sizes it was a bit of a shock. We went through several different brands until we found one that worked really well for him. Surprisingly he does Old Navy’s ultimate straight khakis. They also have a skinny cut and an athletic cut. I was thinking the athletic cut might work for your son.

Update from OP- Gap size 29 x 30 fit perfectly with a belt. Thanks so much for all of your advice!

A bit pricier that the basics, but for winter uniform DS lives in LL Bean flannel-lined khakis like these.

https://www.llbean.com/llb/shop/90057?page=men-s-lined-double-l-chinos-natural-fit-hidden-comfort-waist-plain-front&bc=12-26-590&feat=590-GN1&csp=f&gnrefine=1*FTRS*Lined

I hate that they are part of Walmart now but Bonobos work well with that body type.

Thanks all. OP here- looks like we will be going to the men’s department this week. Thanks for all the suggestions!

My 14 yo DS (5'6" and 125 lbs.) just moved from boys sizing to men's, and I had luck with Docker's. Just bought several pairs from Kohl's.

There were several different cuts, we went with a slimmer one. Waist sizes started at 28".