Conundrum – 41 Year’s Old. What to Wear Out on a Saturday Night in Chicago

I am going to a Fraternity reunion (State school) in Chicago in late October (this year, 2015), roughly a 20 year reunion, covering the 90’s era, oldest person will be late-40s, youngest mid-30s.


It will be very casual; we will be starting at a Bar/Restaurant in Magnificent Mile and will head out from there. But I do want to look well dressed and successful.


I live in LA, it is very easy to dress here, you either go stupidly casual, or over the top stylish.

But I will be in Chicago; I am 41 years old, a silver haired father with a great muscular-skeletal system covered in 10- 15 pounds of goo (too much booze and catered lunch). Some guys will be dressed like slugs, some will step it up. The kids that work for me tell me that a sport coat or well tailored suit is whats up when they go to Vegas. I tell them that I look like I am supposed to be wearing a suit and at my age people will think I am the host of the restaurant if I am not with my Wife.


So I was thinking:

Sport Coat – Slim Tailored Medium Charcoal Gray Wool
Blue Checked Shirt Tailored Dress Shirt (Tucked in Obviously)
Jeans – Jet Black Slim (not Skinny)
Shoes Vintage Black Florsheim Imperial Full Wingtip 5 Nail Suicide Cleat Gunboats


Does this sound appropriate? My wife has no clue and says I will look “fine” (eye roll).
Suggestions are welcome.

Conundrum – 41 Year’s Old. What to Wear Out on a Saturday Night in Chicago