Fashion For Christmas

I realized something about myself after the comments on that last post.  I don't ever look at my husband's clothing anymore.  I honestly did not give it a second thought when I photographed him wearing that clothing or when I published it to the internet for everyone to see.  Then I saw all those comments and looked again and hoo-boy!  Luckily he did put on jeans for the actual dinner (and also the top is a jacket, not a shirt so that came off too).  Dinner was a completely plaid free event.

So here's my predicament.  I told my husband that all my creativity and planning for gifts this year was zapped and if he wanted to get a gift that he actually wanted he should just tell me what it was so I could get it for him.  He didn't even hesitate when he said a belt buckle that could go with nice black pants.  He has a beautiful belt buckle that my parents got him which has copper tones in it that goes well with brown or khaki pants, but not as well with black.

I know what he wants.  He wants to be able to wear this belt buckle with slacks in to work.  I want him to look nice too, wearing something he likes, but I don't want him to look like a caricature of a doctor cowboy.

This poses a problem for me because he wants something western and formal and the two don't often overlap.  Especially not in the under $100 category.

So do I:
1) Swallow hard and get him a belt buckle that I know is the type he wants, but that I don't really think is a more formal look
OR
2) Buy him a nice new formal belt with a more formal buckle?

And if I do go with option 1 where do I find something that could come even close to being appropriate for his work, and his personality.  After all is is an understated man, something overly flashy doesn't ever suit him.

And most importantly, why is my husband always the hardest one for me to shop for?