Need help on 30 year HS reunion outfit?

[SLOshank]

Hello;

My 30th HS reunion is right around the corner. Men will be wearing everything from blazers and slacks to t-shirts and blue jeans.

I bought a very loud western shirt for my upcoming HS reunion (see photo.) It's in my alma mater's colors. I bought it because of the colors, because of the vibe (fun, sarcasm, stupidity) it projects, and believe it or not, because I got a good deal.

I plan to wear it with simple black Levis 501 jeans and a very simple black belt (see photo.) No hat.

I have two questions. First, should I tuck the shirt in, or leave it out? I don't have a pot belly to hide or anything like that.

Second, what sort of footwear? I don't want to wear western boots or even hiking boots. I can't really think of any casual/dress shoes that would go with this? I do think that a simple pair of good old Adidas black Superstars might "work", but I'm really not sure?

They would extend the sarcasm, not make it appear of it I'm really some sort of urban cowboy and they might actually look good in a twisted way with the crazy shirt and Levis?

Any inputs would be appreciated. Thank you.

 

[KILO NOVEMBER]

My fifty-year reunion succumbed to COVID-19 last month.
For shoes, I suggest black suede chukka or chelsea boots.
For the shirt, tuck it.

 

[Modified_last_call]

That shirt is going to make quite the statement.

I don't think athletic shoes are the proper footwear.
How about a nice understated service boot, it can be casual or more formal.
You have to take some pictures at the event and post them here.

Good luck and enjoy

 

[SLOshank]

My fifty-year reunion succumbed to COVID-19 last month.
For shoes, I suggest black suede chukka or chelsea boots.
For the shirt, tuck it.

I had not considered chukkas or chelsea boots, hence my rather extreme choice. Thank you!

 

[SLOshank]

That shirt is going to make quite the statement.

I don't think athletic shoes are the proper footwear.
How about a nice understated service boot, it can be casual or more formal.
You have to take some pictures at the event and post them here.

Good luck and enjoy

Service boots -- another great idea, thank you. I very much want to wear the (ridiculously loud) shirt, but I don't want to appear as if I'm being serious about it. Just imagine an urban cowboy wearing that shirt with a cowboy hat, a big belt buckle and shit-kickers.

My wife did just buy me a bolo tie. I'll leave it loose!

Than you again!