K-man, this one's for you: Suit: solid charcoal gray, single-breasted, two button, notched lapels. The most conservative color and cut of all. Shirt: Solid white broadcloth, medium spread collar, not too dashingly open, not too mafia-closed. Note the button cuffs. NEVER wear French cuffs. Special shout-out to josepidal: that is an ultraconservative lawyer tie. In fact, I got if from the general counsel to the John Birch Society in an ebay sale. Printed twill with a dark blue ground and small silver and royal blue figures; no accent colors. Some might say, Wouldn't a solid tie be more conservative? I reply: In the abstract, maybe. But in context, no. Solid ties are actually seen less than prints in the modern office building. In particular, grenadines are known to be favored by men who enjoy their clothes, and that is not conservative. What about a stripe? Conservative-looking, yes. But risky. Stripe patterns are tied to schools or regiments. Even the ones that really aren't look like they are. So what if you wear one, and one of the partners at your firm went to that school or served in that regiment? What then? I'll tell you what. You are f*cked. Pwned. He will crush your @$$. Your career will be ruined. Now, is that worth the risk? Of course not. Prints are safe. Everyone wears prints. But note well: that is not an iconic print like an Hermes, a Ferragamo, or Vinyard Vines. Stay away from those. Not Conservative. You want a classic looking print of utterly indeterminate provenance. White linen pocket handerchief, square fold, showing less than 1/2". However, there will those for whom the above is not conservative enough. Some partner will say, "Who the f*ck do you think you are to wear that hankie? Hankies are for closers!" Someone else might think the tie clasp too vintage, too old world. The Firm Does Not Want Individuals! The Firm Wants Pliant Comma-Checking Slaves! If so, ditch both accessories, and you will have ultraconservative business dress: Here endeth the lesson.