Wear the belts under the untucked shirt. It'll be like your little secret, and people will get a flash when you lean over or whatever. Girls wear pretty underwear that no one will see - why can't you wear a nice belt that no one will see? Ditto on socks.

Also, a blazer is a good idea. We just bought MuddDude a nice goin-out blazer. It really completes an "upscale casual" outfit. Like, if you wear nice jeans and a dress shirt to a party or a show or a play, the blazer will make you look like you are consciously dressing a bit casual, rather than like sort of a slob.

Thanks, muddgirl. Maybe I'll try that next time I'm wearing a fairly loose shirt. Otherwise the belt kinda bulges.

I'll have to get a blazer that I like. Although I tend to feel a bit warm when I am overdressed.

I’m probably too old to have any fashion sense, so take my opinion with a bit of caution:

Black belt, smooth leather with understated buckle = wallstreet/lawyer/politico.

Brown belt, woven or otherwise matte finished = casual guy, everyday use.

Tooled leather and big silver buckle = fake cowpoke.

Black leather with your name or Harley emblem or other such logo = redneck.

So many options…. You can change your persona just by selection of the belt!

Aaargh, I just can't cope with the great Untucked Shirt conundrum. I've read a couple of times now that untucked shirts are now hopelessly out of fashion. But it's just so much easier when you're used to it.

Come to think of it, that was a couple of years ago. Maybe untucked shirts are back in?

I think guys with their shirt tucked in and no jacket look kinda... uptight

How about a sweater? Oh, it's (supposedly) spring. Well, a polo shirt? There are other options besides buttondowns. You haven't said if this is for work or going-out or what. If it's not too hot wherever you are, a collared shirt under a v-neck looks great on most guys I've seen.

I think guys with their shirt tucked in and no jacket look kinda... uptight, or at least I think I do.

I don't know about uptight. But it looks incomplete to me. That's why I've started wearing suits (but no tie) or a blazer to work even though we're business casual. This annoys my co-workers, but I just think it looks much better than just slacks + tucked in shirt.

For more casual situations, I totally agree with desjardins' sweater advice.