Tagged: When Harry Met Sally
When Harry Met Sally: Harry’s Leather Flight Jacket
Vitals
Billy Crystal as Harry Burns, sarcastic political consultant and recent divorcée
New York City, Fall 1987
Film: When Harry Met Sally…
Release Date: July 14, 1989
Director: Rob Reiner
Costume Designer: Gloria Gresham
WARNING! Spoilers ahead!
Background
One of the most aesthetically pleasing fall movies, Rob Reiner’s romantic comedy When Harry Met Sally celebrated its 35th anniversary earlier this year. Billy Crystal and Meg Ryan—who celebrates her 63rd birthday today—star as the titular enemies-turned-friends-turned lovers. Continue reading
When Harry Met Sally: Harry’s Cream Cable-Knit Sweater
Vitals
Billy Crystal as Harry Burns, sarcastic political consultant and recent divorcée
New York City, Fall 1987
Film: When Harry Met Sally…
Release Date: July 14, 1989
Director: Rob Reiner
Costume Designer: Gloria Gresham
Background
As October advances deeper into colder weather, today’s post celebrates the enduring knitwear selected by costume designer Gloria Gresham for fall style icon Billy Crystal in When Harry Met Sally.
Though he only wears it for two brief scenes in Rob Reiner’s 1989 romantic comedy, Harry Burns’ cream-colored cable-knit sweater remains a cultural touchpoint even nearly 35 years later. Continue reading
When Harry Met Sally: Harry’s Tweed Sports Coat
Vitals
Billy Crystal as Harry Burns, sarcastic political consultant and recent divorcée
New York City, Fall 1987
Film: When Harry Met Sally…
Release Date: July 14, 1989
Director: Rob Reiner
Costume Designer: Gloria Gresham
WARNING! Spoilers ahead!
Background
Today being my wedding day (congratulations to me!) feels like an appropriate time to revisit the style of one of my favorite romantic comedies, When Harry Met Sally. In addition to being a famously great fall movie, Rob Reiner’s chronicle of enemies-becoming-friends-becoming-lovers also demonstrates a surprising parade of great autumnal menswear, from Billy Crystal’s cozy sweaters to military surplus jackets. Continue reading
When Harry Met Sally: A Nomex Flight Jacket on New Year’s Eve

Billy Crystal and Meg Ryan assure their old acquaintance won’t be forgot among fellow New Year revelers as the eponymous leads in When Harry Met Sally… (1989)
Vitals
Billy Crystal as Harry Burns, sarcastic political consultant
New York City, New Year’s Eve 1988
Film: When Harry Met Sally…
Release Date: July 14, 1989
Director: Rob Reiner
Costume Designer: Gloria Gresham
WARNING! Spoilers ahead!
Background
Happy New Year’s Eve!
One of my favorite romantic comedies, When Harry Met Sally… follows its two eponymous leads over twelve years of off-and-on friendship from their contentious meeting during a ride home from the University of Chicago up through a climactic New Year’s Eve party. Continue reading



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