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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.
This would be my vote as well. Also, if you are investing in nice shoes, think about where else you will wear them. You will likely find brown or oxblood more versatile.
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...
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