14. Andy Cohen, Watch What Happens Live

If you&#39;re going to be asking Oprah if she&#39;s ever dipped into the &quot;lady pond,&quot; it&#39;s best to do it in a respectable getup, which is exactly what the gregarious Cohen wears every weeknight in his clubhouse. The Bravo ec favors Boss and Ralph Lauren Black Label suits, smartly swapping in new shirt and tie combinations, in solids to plaids that pop, and finishing it all off with attentio-grabbing socks and burnished Ferragamo wingtips.—M.S.