5. Night Out
When darkness falls, the fun can begin. You’ll need comfortable garbs to sweep her off her feet, and a simple blazer and jean pairing should help you do just that. You could dance the night away in some smart casual pants, or you could pair some dress pants with a distressed leather jacket for a smarter look. Try not to tone down your drapes too much with loafers, or wear sneakers that are too eye-catching. Iridescent, sparkly, fluorescent or spikey shoes have no business being on the dance floor with you, unless you’re a teenager. You can paint the town red with ox-blood brogues, if you like, but that’s about as close to that colour as you can afford to get when you have a fashion conscious lady by your side.
6. Formal Event
When pleasantries and curtsies are in order, you’d do well to don your most dashing formal suit. You know you’ll not only make your date short of breath, but make all the other ladies envious of her when your evening wear matches, too. You could go for silk-satin trims on your suit jacket, a pair of patent black shoes, and a pure silk tie or a bow, or you could simply opt for a two-tone formal suit and an eye-catching overcoat on a chilly night.