LIVE
✦ Loading vintage finds from Amsterdam · Paris · London · Tokyo · New York · Milan · Barcelona · Berlin…

Travel story · New york

Sinatra's New York

From the Village's candlelit bistros to the jazz clubs of Midtown, follow Frank Sinatra's New York — the city that never sleeps, where the night only really begins after midnight and the martinis stay dry.

Sinatra's New York
Wikimedia Commons · Public domain

Day 1: Hoboken roots

Start in Hoboken, across the Hudson, where Frank was born. The ferry back to Manhattan is the same crossing he made thousands of times.

Vintage Harley Davidson women’s fedora hat  Size XL | 100% wool | Made in USA
Vintage Harley Davidson women’s fedora hat Size XL | 100% wool | Made in USA

Day 2: The Village and the joints

The clubs of Greenwich Village were his proving ground. Walk along MacDougal Street and find a place where live jazz still plays. Order a dry martini, no discussion.

Vintage 1950s Royal Stetson Stratoliner Fur Felt Fedora Hat Barth's No Size See
Vintage 1950s Royal Stetson Stratoliner Fur Felt Fedora Hat Barth's No Size See

Day 3: Midtown, after dark

Finish in Midtown, where the Rat Pack ruled. A late dinner and a walk beneath the lights of Times Square. Do it your way.

Vintage 50s Dobbs Fifth Avenue Black Fedora/Homburg Hat 7 1/4 Large - READ
Vintage 50s Dobbs Fifth Avenue Black Fedora/Homburg Hat 7 1/4 Large - READ

Along the way

  1. 01

    Hoboken

  2. 02

    MacDougal Street

  3. 03

    The Waldorf Astoria

  4. 04

    P.J. Clarke's

  5. 05

    Times Square

  6. 06

    Carnegie Hall