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In a Chicago Museum on a Saturday night you can wear any of the options you listed. Wear what you feel most comfortable in - that tends to come through more than forcing something to conform with what you think you should wear.
I agree with the tuxedo comments. Don't try to fake it.
The black or suede?
Kidding. Alden makes nice boots that look a lot like that. I believe you can get them at J Crew these days for about $500. it's a popular style, so there should be multiple options at lesser price points. LL Bean signature has one, regular LL Bean has a Katahdin...
I've got a black/dark charcoal BB cashmere turtle neck sweater in the back of my closet somewhere. I've been thinking of taking it out when it gets cold. It's not super fitted if I remember, but is fine under a jacket. I think I'm in the market for a chunkier turtle neck. Maybe Irish knit...
I saith keep this one as advertised - "So, just to be clear: Tie? OK. No tie? OK. Square/No square? Yes. Pents/No Pents: Well, hopefully pents, but I suppose that's up to you." - and make s brown suit contest for next week. Suits have pents.
A lot of this comes down to personal taste. I like stripes, but some would call them "schoolboy ties." You can't go wrong with the Brooks Brothers #1 stripe in blue or red.
Oh yeah, don't buy a black tie until you have about a dozen others. Navy will be just as versatile and not make...