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Posts by deadAngle

They look uncomfortable.
All of your suggested jackets would be reasonable with black pants.  Personal choice would be a medium scale black and white houndstooth or shepherd's check jacket.
Do any of your other shoes crease in similar areas?  It may be due to your gait, how you use your ankles, or the direction your feet point.  My own gait gives incredibly deep creases in the front of all of my shoes despite shoe tree use because of long steps and using my toes to push off the ground, and it's always kind of baffling to me to see other people's well-worn shoes with mild or no creasing in that area.  Nevertheless, while some of my shoes exhibit light ankle...
No love for bellows pockets?
A dark red tie would probably round out things nicely; I'd be cautious about a blue plaid unless it matched your date's dress.  With everything else being black and white, a black long tie trends towards funeral territory. 
Would work better with a higher button stance so the bottom buttons were in line with the pockets, but it seems nice enough. 
It wouldn't look out of proportion with wider spacing between the buttons and a wider placket. 
And don't write off the link button front - it's quite useful.  Keeps the roll of the lapels identical to get the unbuttoned jacket effect while still keeping things neat, shows off a little more of the cummerbund, and allows you to loosen your jacket after a big meal.
I don't go by the logic that "nobody should see them" because I'll take my jacket off at some point in the day.  If I wasn't going to take off my jacket I could also wear a black belt with brown shoes but nobody would disagree that that would be the wrong choice unless that was the only belt I had.  The going theory is that both the suspenders and the tie are vertical elements that occupy the same space on the shirt and should reflect one another in some way - but like a...
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