From The Archives: “Dress Like The Chairman”

In honor of Frank Sinatra’s birthday (he would be a cool 100 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.

Come Fly With Me

Frank Sinatra Come Fly With Me Wingtip Look

Hat: Paul’s Hat Works “Downtown” in rabbit felt, preferably with extra-wide ribbon.
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.

Days Of Wine And Roses

Frank Sinatra Wine And Roses Wingtip Look

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

Swing Easy

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)
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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.

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