His
Cocktails anyone: I love a man in a navy suit (especially one that fits really, really well). Guys, invest in bespoke. You will wear it a lot and get your money’s worth. My favorites are OliverRowan Bespoke and for custom, BLVDier. Off the rack I think Isaia does a great job. As for the shirt, Trumaker all the way. They are built-to-fit shirts. You get measured once, and can order endless perfect fitting shirts. Keep the tie solid because of the patterned shirt but add some flare with a patterned pocket square.
Hers
Winter is not only about dark colors. Go for a dove grey monochromatic look from head to toe. A turtleneck tucked into, or left out of, a draped skirt is so elegant and unexpected. When going for a mono look be sure to choose fabric with some texture. The bootie is a knock-off of a Dior bootie. This one is only $85 from Public Desire. Yes you can pull this look off!
clutch by Olympia Le Tan.
Number Three