Jack Donaghy is an interesting mention. While I like the CBD fabrics and tie patterns he chooses, he seems like the quintessential example of a man wearing a poorly tailored suit (and often in sloppy fashion). His jacket sleeves are way too long, and in wider shots, you can see a pound of fabric gathered around his ankles because the pants have not been hemmed to the right length. Also, his tie knots are frequently a mess, and his tie length is often a disaster (usually partly hidden by his buttoned jacket).
I assume it's largely a budgeting issue for the show, and to the show's credit, they do a good job concealing how poorly dressed he is probably 75% of the time. But, even saying that, he usually buttons the lower button on his jacket.