Dress Like The Chairman

In honor of Frank Sinatra’s birthday (he would be a young 97 today), we’ve put together some looks based on his album covers. These looks are good for jet-setting, formal occasions, and, well, just swinging.

Frank Sinatra Come Fly With Me Wingtip Look

Hat: Paul’s Hat Works “Downtown” in rabbit felt (We’re still working with the ladies at Paul’s Hat Works to get some extra-wide hat ribbon like Sinatra often donned on his headgear; let us know if you’re interested in your own wide-ribboned hat.)
Jacket: Wingtip two-button, notch lapel with grey and blue pinstripes.
Shirt: Antonio Valente French-cuffed dress shirt.
Cufflinks: Tokens and Icons Syracuse stadium seat cufflinks.
Pocket Square: Peter Millar pin dot in green.
Tie : Peter Millar “Mogador” track stripe.

Frank Sinatra Wine And Roses Wingtip Look

Hat: Paul’s Hat Works “Trilby” in rabbit felt (currently available through Bespoke).
Jacket: Wingtip peak, grosgrain lapel, one button (covered) dinner jacket.
Pocket Square: Wingtip silk satin in silver.
Bow Tie: Wingtip satin Charvet cut.

Frank Sinatra Swing Easy Wingtip Look

Hat: Paul’s Hat Works “Fillmore” in rabbit felt
Jacket: Peter Millar “SB Milano”, 100% wool (please contact Bespoke for details on MTO Peter Millar apparel)
Vest: Wingtip “Dean” in smoky purple herringbone
Shirt: Antonio Valente trim-fit dress shirt in light pink.
Tie: Wingtip polka-dot in purple.
Pocket Square: Wingtip silk satin in Champagne.

(please contact Bespoke for details on all Wingtip apparel)

Be Sociable, Share!


David is Wingtip's storyteller. In addition to editing the Modern Gentleman's Blog, he has written for Wax Poetics, The Source, SF Weekly, and the East Bay Express, and others. His inspirations include Rumble Fish, Paul's Boutique, and Balzac. He studied English at the City University of New York at Hunter College and journalism at the University of Southern California. He lives in Berzerkeley with his wife and daughter.

Submit a comment

Your email address will not be published. Required fields are marked *