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519 Penny Loafer Photos and High-Res Pictures

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Browse 519 authentic penny loafer photos, pictures, and images, or explore ivy league or penny shoe to find the right picture.

Dwayne Johnson is seen on July 31, 2019 in New York City.

Celebrity Sightings In New York - July 31, 2019

View of women's legs as they stand outside at a park in New York, ca.1940s.

Standing Around

Portrait of American actor and comedian Soupy Sales as he leaps in the air with a mock terrified expression on his face, August 22, 1969.

Soupy Sales In The Air

Sam Claflin and Jack O'Connell attend day one of the Audi Polo Challenge at Coworth Park on May 30, 2015 in London, England.

Audi Polo Challenge - Day 1

Dakota Fanning and boyfriend Jamie Strachan out in downtown Manhattan. On September 16, 2013 in New York City.

Celebrity Sightings - Bauer-Griffin - 2013

David Corenswet is seen in Midtown on July 09, 2025 in New York City.

Celebrity Sightings In New York City - July 09, 2025

Justin Bieber and Hailey Bieber are seen on December 06, 2022 in New York City.

Celebrity Sightings In New York City - December 06, 2022

Justin Bieber and Hailey Bieber are seen on December 6, 2022 in New York City.

Celebrity Sightings In New York City - December 06, 2022

Singer YUNGBLUD is photographed for Attitude magazine on July 28, 2019 in London, England.

YUNGBLUD, Attitude UK, September, 2019

Ty Dolla $ign and guest attend the Pre-GRAMMY Gala and GRAMMY Salute to Industry Icons Honoring Sean "Diddy" Combs on January 25, 2020 in Beverly...

Pre-GRAMMY Gala and GRAMMY Salute to Industry Icons Honoring Sean "Diddy" Combs - Arrivals

Edgar Ramirez attends "Wasp Network" photocall during the 76th Venice Film Festival at Sala Grande on September 01, 2019 in Venice, Italy.

"Wasp Network" Photocall - The 76th Venice Film Festival

Edgar Ramírez attends "Wasp Network" photocall during the 76th Venice Film Festival at Sala Grande on September 01, 2019 in Venice, Italy.

"Wasp Network" Photocall - The 76th Venice Film Festival

Richard Cabral attends the premiere of FX's "Mayans M.C." Season 2 at ArcLight Cinerama Dome on August 27, 2019 in Hollywood, California.

Premiere Of FX's "Mayans M.C." Season 2 - Arrivals

Terry Crews attends "America's Got Talent" Season 14 Live Show at Dolby Theatre on August 13, 2019 in Hollywood, California.

"America's Got Talent" Season 14 Live Show Red Carpet

Terry Crews attends "America's Got Talent" Season 14 Live Show at Dolby Theatre on August 13, 2019 in Hollywood, California.

"America's Got Talent" Season 14 Live Show Red Carpet

Terry Crews attends "America's Got Talent" Season 14 Live Show at Dolby Theatre on August 13, 2019 in Hollywood, California.

"America's Got Talent" Season 14 Live Show Red Carpet

Terry Crews attends "America's Got Talent" Season 14 Live Show at Dolby Theatre on August 13, 2019 in Hollywood, California.

"America's Got Talent" Season 14 Live Show Red Carpet

Terry Crews attends "America's Got Talent" Season 14 Live Show at Dolby Theatre on August 13, 2019 in Hollywood, California.

"America's Got Talent" Season 14 Live Show Red Carpet

Terry Crews attends "America's Got Talent" Season 14 Live Show at Dolby Theatre on August 13, 2019 in Hollywood, California.

"America's Got Talent" Season 14 Live Show Red Carpet

Prince Kyril of Bulgaria receives 'Mallorquin del Verano' award 2019 at Valparaiso Hotel on August 02, 2019 in Palma de Mallorca, Spain.

Prince Kyril Of Bulgaria Receives 'Mallorquin Del Verano' Award 2019

Prince Kyril of Bulgaria and Katharine Butler attend 'Mallorquines del Verano' award 2019 at Valparaiso Hotel on August 02, 2019 in Palma de...

Prince Kyril Of Bulgaria Receives 'Mallorquin Del Verano' Award 2019

Dwyane 'The Rock' Johnson at GMA on July 31, 2019 in New York City.

Celebrity Sightings In New York City - July 31, 2019

Dwyane 'The Rock' Johnson at GMA on July 31, 2019 in New York City.

Celebrity Sightings In New York City - July 31, 2019

Actress Monica Bellucci and Nicolas Lefebvre attend ELLE Charity Gala 2019 to raise funds for cancer at Intercontinental Hotel on May 30, 2019 in...

ELLE Charity Gala 2019 In Madrid

Actress Monica Bellucci and Nicolas Lefebvre arrive at ELLE Charity Gala 2019 to raise funds for cancer at Intercontinental Hotel on May 30, 2019 in...

Celebrity Sighting In Madrid - May 30, 2019

Actress Monica Bellucci and Nicolas Lefebvre arrive at ELLE Charity Gala 2019 to raise funds for cancer at Intercontinental Hotel on May 30, 2019 in...

Celebrity Sighting In Madrid - May 30, 2019

Ross Lynch attends the amfAR Cannes Gala 2019 at Hotel du Cap-Eden-Roc on May 23, 2019 in Cap d'Antibes, France.

amfAR Cannes Gala 2019 - Cocktail

Actor Samuel L. Jackson is photographed for Gentleman's Journal magazine on March 29, 2018 in Los Angeles, California.

Samuel L. Jackson, Gentleman's Journal, May 1, 2018

Actor Samuel L. Jackson is photographed for Gentleman's Journal magazine on March 29, 2018 in Los Angeles, California.

Samuel L. Jackson, Gentleman's Journal, May 1, 2018

Pixie Lott launches her Autumn/Winter Fashion Range for Lipsy at House of Fraser on September 28, 2010 in London, England.

Pixie Lott Launches Her Autumn/Winter Fashion Range for Lipsy - Photocall

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View of Penny Loafer shoes on September 18, 2008 in Milan, Italy.

Rossetti One Presents Penny Loafer Cocktail Party

Guest wears long wavy blonde hair parted in the center, small gold stud earrings, a navy suede shoulder bag with a top flap, long strap and gold...

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Street Style - Paris Fashion Week - Menswear Spring/Summer 2026 - Day Five

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Fashion Photo Session In Paris - June 2024

Marlies Pia Pfeifhofer is seen wearing a charcoal grey wool jacket with a soft, structured silhouette, a classic button-front closure and a slightly...

Street Style - Munich - January, 2026

Guest wears long light-brown hair down with a center part, matte-black over-ear headphones, black round acetate eyeglasses, a short white pearl-bead...

Street Style At Copenhagen Fashion Week SS26 - Day 4

Guest wears black over-ear headphones and round black eyeglasses, with long light brown hair parted at the center and worn loose; a short pearl-bead...

Street Style At Copenhagen Fashion Week SS26 - Day 4

Sophia Geiss seen wearing COS blue denim oversized, wide-leg jeans and Marco Polo white leather loafer shoes keep the look comfortable and casual, on...

Street Style - Berlin - April, 2025

Hailey Bieber is seen on December 6, 2022 in New York City.

Celebrity Sightings In New York City - December 06, 2022

1950s HUGGING DANCING TEENAGE COUPLE IN LIVING ROOM

1950s HUGGING DANCING...

1960s HIGH SCHOOL STUDENTS BOYS GIRLS HOLDING BOOKS TALKING OUTSIDE SCHOOL

1960s HIGH SCHOOL STUDENTS...

1950s TEEN TEENAGE GIRL HOLDING SCHOOL BOOKS WALKING DOWN SIDEWALK FRONT OF BRICK HOUSE STUDENT HIGHSCHOOL

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1950s GIRLS PLAYING SCRABBLE IN RECREATION ROOM WITH BOY CHANGING RECORDS

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1950s MALT SHOP INTERIOR...

Erin Whitehead, fashion detail, attends the screening of 'Hairpin Bender' at Downtown Independent Theater on September 28, 2015 in Los Angeles,...

Screening Of "Hairpin Bender"

Guest wears a light blue fuzzy knit cardigan, a navy-and-white striped long-sleeve top, a beige pleated mini skirt with a leather-like finish, white...

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Marlies Pia Pfeifhofer is seen wearing a charcoal grey wool jacket with a soft, structured silhouette, a classic button-front closure, a classic...

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Guest wears cream knit lace knee-high socks and black-and-white leather penny loafers shoes with flat soles, outside Miu Miu, during Paris Fashion...

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Mirja Klein is seen wearing an oversized dark olive Enora faux leather jacket with a pointed collar, silver hardware detailing and dropped shoulders...

Street Style - Munich - September, 2025

Mirja Klein is seen wearing an oversized dark olive Enora faux leather jacket with a pointed collar, silver hardware detailing and dropped shoulders...

Street Style - Munich - September, 2025

Mirja Klein is seen wearing an oversized dark olive Enora faux leather jacket with a pointed collar, silver hardware detailing and dropped shoulders...

Street Style - Munich - September, 2025

Mirja Klein is seen wearing an oversized dark olive Enora faux leather jacket with a pointed collar, silver hardware detailing and dropped shoulders...

Street Style - Munich - September, 2025

Guest is seen wearing a taupe blazer with a pair of brown leather penny loafers at the Rave Review show during Copenhagen Fashion Week day two on...

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Brett Staniland and Scott Staniland are seen wearing an olive green double breasted blazer with striped tie, shorts, brown loafers, a white shirt,...

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The fall opening of the club <Area> where glass cases of live animals were part of the "natural history" theme as a replica of the American Museum of...

<Area> Club Opening

Younes Bendjima attends the Dior Men's Fall 2020 Runway Show on December 03, 2019 in Miami, Florida.

Dior Men Fall 2020 Runway Show

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Edgar Ramírez attends "Wasp Network" photocall during the 76th Venice Film Festival at Sala Grande on September 01, 2019 in Venice, Italy.

"Wasp Network" Photocall - The 76th Venice Film Festival

Dwayne Johnson is seen outside good morning america on July 31, 2019 in New York City.

Celebrity Sightings In New York City - July 31, 2019

Zachary Quinto is seen at 'Jimmy Kimmel Live' on June 05, 2019 in Los Angeles, California.

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