(1) Slacks for both looks are Asos River Island Skinny Fit Trousers in Black Polka Dot ($45.37). These are MICRO DOTS - so tiny, barely visible unless you look closely. It's very subtle - zoom in, if you don't believe me!
Formal Option, from the bottom up:
(2) Take inspiration from the smoking jacket with Brooks Brothers Black Velvet Slippers ($248)
(3) Keep it clean and simple with Brooks Brothers Supima Non-Iron Extra Slim-Fit Dress Shirt ($92)
(4) Polishing off the preppy theme - top it with Black Fleece Cashmere Unconstructed Patch Pocket Jacket ($1000)
Extra credit: Top it off with a simple bow tie. Or leave the collar open to keep it less stiff.
Casual Option, from the bottom up:
(5) Classic Bass Logan Weejuns in Black ($108). Remember to roll your cuffs so you don't look like your dad!
(6) New England Shirt Company Brushed Cotton Button Down ($188)
(7) Add a pop of color. J.Crew Merino half-zip sweater in heather port ($89.50)
(8) Last detail - keep your sunglasses cool Ray-Ban Classic Clubmaster ($145)
Final notes: Key to keeping this look modern, not fuddy-duddy, is in the details - tailored, slim fits, rolled cuffs.