What would Frank Sinatra wear on a first date?

There’s something to be said about dressing the part of a gentleman. In part, it’s paying respect to a time when men wouldn’t step out of the house without a suit and style was synonymous with class. Fashion was a way of life for Frank Sinatra, who once crooned: “You either got or you haven’t got style. If you’ve got it, you stand out a mile.” Known for believing that black was the only acceptable shoe color and a hat wasn’t a hat until it was tilted, Sinatra’s style was impeccable from head to toe. Even if you can’t carry a tune like Ol’ Blue Eyes, you can still emulate his iconic look — and stand out by a mile.


1. Suit up

If you’re abiding by the Sinatra rule book, step one is a made-to-measure suit and custom shirt. A good tailor is a man’s best friend so find one, love him, and never let him go. You’ll never pull off pinstripes like Sinatra if you’re swimming in your suit.

Park Avenue Cap-Toe Oxford shoe. (Photo credit: allenedmonds.com)

2. Shine your shoes

If you want to see the soul of a man, look down. Few things can ruin a polished look like a pair of dingy oxfords. If you want to impress like Sinatra, keep the swagger in your step by ensuring your shoes are a reflection of your attention to detail. Much like cufflinks, immaculate shoes might seem like a relatively small component to a look, but they go the distance. If you so much as consider leaving the house in battered or dull shoes, you might as well let your girlfriend’s cat roll around on your suit jacket too. You have no business being in public.


3. Orange is the new black

Sinatra considered orange the happiest color. Fall is the perfect time to test out this rustic shade by way of shirt, tie, or pocket square, preferably paired with a dark blue or grey suit.

Good Boy fedora. (Photo credit: goorin.com)

4. A fedora will make or break you

A man should never let his hat wear him. The first order of business when flaunting a fedora is confidence. This tipped hat - cocked to the side - was a Sinatra staple. Although it’s not an easy accessory, it can be incorporated into an outfit the same way a vibrant tie or colourful pocket square can become an extension of a look without distracting from it. The secret is attitude. Try a few different hats, worn at different angles, to see what works.

November 29, 2017 by Victor Custom Shirts