Aloofus I'm going to be nitpicky because menswear is my passion
Good effort but I think this can be improved
Also, you said you liked a well dressed classy style. Seriously go to youtube.com/hespokestyle and watch every one of his videos. He has your complexion, is ealry 40s is around your height (I think he's 5'9), and has an incredible dressy-but-still-sexy-style that works great IMO for older men
He even has a video precisely on wearing a blazer with jeans, as you are doing: https://www.youtube.com/watch?v=b_DVCmHdO-c
I also think you can put some product in your hair but I'm also aware that there's a bit of thinning going on so I'm not sure how vialbe that is
1. As noted by DNPTHC the jeans need shortening and tapering
2. You're wearing a suit jacket but you're trying to pass it off as a blazer/sport coat. I can tell that this is a suit jacket because of the more structured shoulders (the more structure/padding in the shoulder, the more formal a garment). For something as casual as jeans, I would've worn a sport coat that is more casual, with softer/no padding in the shoulders, patch pockets, and a more casual fabric like a hopsack weave wool (I can't tell what fabric the blazer is, but I suspect it's a worsted wool. It's fine to wear a worsted wool blazer with jeans, it's a very preppy Brooks Brothers looks, but those sorts of blazers usually also have contrasting brown or gold/brass buttons).
4. Shirt sleeves can be shortened a tiny bit, maybe around an inch or so
5. Jacket sleeves need to be shortened an inch, so that some shirt cuff shows. Your tailor should've picked up on that.
The jacket itself looks fine. Nice high gorge, nice width on the lapels. I'd keep the jacket and buy a pair of matching pants made of the same fabric so you have a nice suit.
