Twenty Year Reunion

Khakis, blue blazer, gingham top, blue tie, white pocket square. Classic, simple, safe, and not looking like you are trying too hard.

Congrats (I think) on the considerably younger woman.

Tell us more about the mrs. sheep incident, what happened, bro?

It is no rib, sorry to hear that, it really is a terrible thing and I hope things will work out for the best.

not sure how SF approve or credible this WSJ writeup, but interesting read... http://online.wsj.com/article/SB10001424052748703789104576273054180897510.html

So here's my question(s). Bear with me as they are slightly open-ended but will help to get a better understanding of your circumstances and motivations (I hope).

What do you want to convey to your peers? (i.e. do you want to be the "look at me now" guy or they "I'm quietly successful" guy; IME this depends greatly on your social standing in high school)

What are the people you went to high school like and do you want to fit into their norms? If this is a Cape Cod event things could get pretty WASPy. You trying to break the mold or do you want to look like a long-lost Kennedy?

How old is the girl and do you see her age/looks affecting what you hope to wear? (This one is bit personal but women always have some impact on how we leave the house, for better or for worse)

These are definitely prodding questions but the fact that you have uncertainty in what you should wear would suggest you might need to figure out why you are uncertain.

For the record I'd show up 2 hours late, bombed, in a stolen taxi, naked. Just as they remember me...

Sport coat (not a navy blazer), mildly patterned dress shirt (maybe something more exciting than a blue/white pattern, perhaps a pink or lavender), no tie, dress pants, great shoes. Looks sharp without looking like you're trying too hard.

My question is why you are taking "a considerably younger woman" with you to a high school reunion? I went to my 20-year high school reunion two years ago and can't imagine a +1 (not to pick at an open wound, unless she was a long-time significant other/wife who knows several people who will be there) enjoying herself other than for the fact she is there with you. Unless you've stayed unusually close to several of your classmates, for most of the time there, you're going to be talking to people you likely haven't spoken to for 10 or 20 years and likely won't speak to again for 10 or 20 years. I can't imagine enjoying myself at a girlfriend's reunion, listening to her and her friends I will likely never see again talk about somehing that happened in 1989 during Geometry class at a high school I didn't attend. I also think the age difference will be more readily evident in a group of people who all graduated together (and are therefore essentially the same age) and their signifcant others, most of whom will be within 3 or 4 years of the same age.

Obviously, the decision has been made and the invitation has been extended/accepted, so it's a moot question. There is no way to ask this directly without sounding harsh, but I'm curious if it's a "Hey, guys/gals, look what I'm shagging these days." sort of thing.

Firstly, congrats on the date.

So I'm sure some here would disagree but to me this is a huge factor into what you should wear. From my (younger) perspective I feel like upper-30's is an odd time where you're not sure if you should be dressing like an early 40s dad or a early 30s yuppie. I see it happen all the time at formal work functions and it freaks me out.

I'd suggest a suit ("fancier" setting + more formal occasion justifies) that has a slightly aggressive cut. This looks like you're grown up enough to wear a well-tailored suit yet you're young enough to pull off a sharper silhouette (this is how you got the arm candy). I'd go for either navy with a bit of sheen or a subtle yet present pin stripe here.

Open collared shirt. Crisp white or pale blue. Higher collar stance. 2 buttons unbuttoned. A bit of sheen or texture here would also help. Contrasting pocket square but nothing too peacock; just something to break things up/add a bit of color.

For shoes wear something with a sleek last. Think dub monk or an Italian loafer. I'd avoid lace-ups as that looks like you just left the office.

From your fit pics you seem to be rather tall and lean. I think this look will be easy to pull off and make you look relaxed yet polished. Again just my $0.02.

All sound like perfectly good reasons to me. Just let her know you appreciate her taking one for the team and that you'll make it up to her. Then, deliver on that promise within an hour of leaving the reunion.