So anyway, what's it going to be, a little formal in some fancy restaurant, or something a bit more casual? At any rate, bring a jacket that you can put over her shoulder if it gets a little too chilly.
The more formal option
Start off with a crisp white shirt, then trousers and a jacket to match. Top it off with a bow tie, a pocket square. Wear brown leather instead of black. And maybe you could ditch the watch. After all, why would you be keeping track of time when you have a lovely lady by your side? Try a cuff or a bracelet instead.
Tropical wool jacket and suit trousers by Marc Jacobs.
MELINDAGLOSS officer collar shirt.
Paul Smith untied bow tie.
Embroidered glasses handkerchief from East Dane Gifts.
Giles & Brother railroad spike cuff.
D-ring belt from Anderson's.
Loake 1880 Cannon monk strap shoes.
Yes, wear jeans. But none of those faded and distressed types, please, and go for something that ironically is just a bit more formal than most denim. Wear any shirt you fancy but some color is suggested. And like I said, bring a jacket. Brown leather.
N.Hoolywood wool blazer.
Han Kjobenhavn classic shirt.
Petit standard brut stretch jeans from A.P.C.
Nixon sentry chrono watch.
Rugged brass belt from Rag & Bone.
Cole Haan Preston whole cut oxfords.
Have a romantic and awesome Valentine's, y'all!