Jessica Simpson Outfits and Style

Jessica Simpson is an American singer, actress, fashion designer, and author. She has long been a style icon and has fun with fashion. Her look tends towards feminine, flirty styles, often in bright colors and with unexpected details. She loves to play with accessories and oversized sunglasses are a staple of her streetwear looks.

Street Style

Jessica Simpson in an Emerald Green RVN Rib Lapel Jacket and Pants

2022-05-17
1/3
Jessica Simpson kept the St Patty's celebration going later into the year, opting for an Emerald Green Engineered Rib Lapel Jacket and Pants from RVN ($710). ... more

Street Style

Jessica Simpson – Leopard Midi Dress – Dolce & Gabbana

2021-09-20
1/3
Jessica Simpson amped up the glam -- and continued her trend of animal-print and earth-toned pieces -- while wearing a Leopard Midi Dress from Dolce & Gabbana and Gold Sundance 140 Sandal from Aquazzura ($795). ... more

Street Style

Jessica Simpson – Black Ribbed Merino Wool Turtleneck Maxi Dress – Balmain

2020-10-21
1/3
Jessica Simpson was seen in February 2020 wearing a Black Ribbed Merino Wool Turtleneck Maxi Dress from Balmain ($1,310), Black Hyper Pointed-Toe Knee Boot from Stuart Weitzman, a Black The Shoulder Pouch Leather Bag from Bottega Veneta ($2,800), Black 54mm Square Sunglasses from Gucci and Gold 3 Inch Samira Hoops from Jennifer Fisher ($650). ... more

Street Style

Jessica Simpson – Black Leather Trench – Frame

2020-05-01
1/3
Jessica Simpson was spotted wearing a Black Leather Trench from Frame ($2,495), Snake-Embossed Klark Tall Boots from Villa Rouge ($275) and Havana Brown GG0178S Sunglasses from Gucci ($248). ... more

Street Style

Jessica Simpson – Black Lace Sleeve Tuxedo Jacket – Alexander McQueen

2020-04-22
1/3
Jessica Simpson was spotted wearing a Black Lace Sleeve Tuxedo Jacket from Alexander McQueen ($3,390), Black Le Leather Leggings from Frame ($950), Black Patent Leather Janis Pointed Toe Platform Pumps from Saint Laurent ($840) and a Black The Shoulder Pouch Leather Bag from Bottega Veneta ($2,800). ... more

Street Style

Jessica Simpson – Pink Crepe Slim Fit Blazer – Alexander McQueen

2020-03-03
1/3
Jessica Simpson was seen wearing a Pink Crepe Slim Fit Blazer from Alexander McQueen ($1,995), Pink Mid-Rise Flared Crêpe Pants from Alexander McQueen ($745) and a The Rockstud Quilted Leather Shoulder Bag from Valentino ($2,895). ... more

Street Style

Jessica Simpson – Brown Knit Turtleneck Sweater – Frame

2020-02-20
1/3
Jessica Simpson was seen wearing a Brown Knit Turtleneck Sweater from Frame ($450), Brown Cropped Leather Flared Pants from Frame ($950), a Marcie Mini Fringed Textured-Leather Shoulder Bag from Chloé ($1,150), Brown Billy Suede Plateau Ankle Boots from Saint Laurent ($1,595) and Gold Samira Hoop Earrings from Jennifer Fisher ($650). ... more

Street Style

Jessica Simpson – Snake Print Chenille Turtleneck Midi Dress – Alexander Wang

2020-02-15
1/3
Jessica Simpson was spotted in New York wearing a Snake Print Chenille Turtleneck Midi Dress from Alexander Wang ($795), Red Danger Klark Tall Boots from Villa Rouge ($275), a Black Texture-Leather Biker Jacket from Balenciaga ($2,745) and Red Square-Frame Sunglasses from Gucci ($420). ... more

Street Style

Jessica Simpson – Neon Pink Belted Shearling-Trimmed Patent-Leather Coat – Saks Potts

2020-02-12
1/3
Jessica Simpson was seen in New York wearing a Neon Pink Belted Shearling-Trimmed Patent-Leather Coat from Saks Potts ($1,705), a Peony Floral Damask Belle Jumpsuit from Staud ($345), Pink Round Monocolor Sunglasses from Gucci ($320) and a Pink The Tall Story Tote from Alexander McQueen ($2,590). ... more

Street Style

Jessica Simpson in a Stand Studio Snake-Effect Jumpsuit for Jimmy Kimmel Live

2020-02-08
1/3
Jessica Simpson was seen in Los Angeles wearing an Amiya Snake-Effect Faux Leather Jumpsuit from Stand Studio ($480) and Snake-Embossed Klark Tall Boots from Villa Rouge ($275). ... more

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Street Style

Jessica Simpson in an Emerald Green RVN Rib Lapel Jacket and Pants

2022-05-17
Jessica Simpson
Photo Credit: IG @jessicasimpson
Jessica Simpson kept the St Patty's celebration going later into the year, opting for an Emerald Green Engineered Rib Lapel Jacket and Pants from RVN ($710).
See All Jessica Simpson Outfits

Street Style

Jessica Simpson – Leopard Midi Dress – Dolce & Gabbana

2021-09-20
Jessica Simpson
Photo Credit: IG @jessicasimpson
Jessica Simpson amped up the glam -- and continued her trend of animal-print and earth-toned pieces -- while wearing a Leopard Midi Dress from Dolce & Gabbana and Gold Sundance 140 Sandal from Aquazzura ($795).
See All Jessica Simpson Outfits

Street Style

Jessica Simpson – Black Ribbed Merino Wool Turtleneck Maxi Dress – Balmain

2020-10-21
Jessica Simpson
Photo Credit: IG @jessicasimpson
Jessica Simpson was seen in February 2020 wearing a Black Ribbed Merino Wool Turtleneck Maxi Dress from Balmain ($1,310), Black Hyper Pointed-Toe Knee Boot from Stuart Weitzman, a Black The Shoulder Pouch Leather Bag from Bottega Veneta ($2,800), Black 54mm Square Sunglasses from Gucci and Gold 3 Inch Samira Hoops from Jennifer Fisher ($650).
See All Jessica Simpson Outfits

Street Style

Jessica Simpson – Black Leather Trench – Frame

2020-05-01
Photo Credit: IG @jessicasimpson
Jessica Simpson was spotted wearing a Black Leather Trench from Frame ($2,495), Snake-Embossed Klark Tall Boots from Villa Rouge ($275) and Havana Brown GG0178S Sunglasses from Gucci ($248).
See All Jessica Simpson Outfits

Street Style

Jessica Simpson – Black Lace Sleeve Tuxedo Jacket – Alexander McQueen

2020-04-22
Photo Credit: IG @jessicasimpson
Jessica Simpson was spotted wearing a Black Lace Sleeve Tuxedo Jacket from Alexander McQueen ($3,390), Black Le Leather Leggings from Frame ($950), Black Patent Leather Janis Pointed Toe Platform Pumps from Saint Laurent ($840) and a Black The Shoulder Pouch Leather Bag from Bottega Veneta ($2,800).
See All Jessica Simpson Outfits

Street Style

Jessica Simpson – Pink Crepe Slim Fit Blazer – Alexander McQueen

2020-03-03
Photo Credit: IG @jessicasimpson
Jessica Simpson was seen wearing a Pink Crepe Slim Fit Blazer from Alexander McQueen ($1,995), Pink Mid-Rise Flared Crêpe Pants from Alexander McQueen ($745) and a The Rockstud Quilted Leather Shoulder Bag from Valentino ($2,895).
See All Jessica Simpson Outfits

Street Style

Jessica Simpson – Brown Knit Turtleneck Sweater – Frame

2020-02-20
Photo Credit: IG @jessicasimpson
Jessica Simpson was seen wearing a Brown Knit Turtleneck Sweater from Frame ($450), Brown Cropped Leather Flared Pants from Frame ($950), a Marcie Mini Fringed Textured-Leather Shoulder Bag from Chloé ($1,150), Brown Billy Suede Plateau Ankle Boots from Saint Laurent ($1,595) and Gold Samira Hoop Earrings from Jennifer Fisher ($650).
See All Jessica Simpson Outfits

Street Style

Jessica Simpson – Snake Print Chenille Turtleneck Midi Dress – Alexander Wang

2020-02-15
Jessica Simpson wears all red at the View Studios on February 05, 2020 in New York City.
Photo Credit: FZS / MEGA
Jessica Simpson was spotted in New York wearing a Snake Print Chenille Turtleneck Midi Dress from Alexander Wang ($795), Red Danger Klark Tall Boots from Villa Rouge ($275), a Black Texture-Leather Biker Jacket from Balenciaga ($2,745) and Red Square-Frame Sunglasses from Gucci ($420).
See All Jessica Simpson Outfits

Street Style

Jessica Simpson – Neon Pink Belted Shearling-Trimmed Patent-Leather Coat – Saks Potts

2020-02-12
Photo Credit: MEGA
Jessica Simpson was seen in New York wearing a Neon Pink Belted Shearling-Trimmed Patent-Leather Coat from Saks Potts ($1,705), a Peony Floral Damask Belle Jumpsuit from Staud ($345), Pink Round Monocolor Sunglasses from Gucci ($320) and a Pink The Tall Story Tote from Alexander McQueen ($2,590).
See All Jessica Simpson Outfits

Street Style

Jessica Simpson in a Stand Studio Snake-Effect Jumpsuit for Jimmy Kimmel Live

2020-02-08
Photo Credit: RB/Bauergriffin.com / MEGA
Jessica Simpson was seen in Los Angeles wearing an Amiya Snake-Effect Faux Leather Jumpsuit from Stand Studio ($480) and Snake-Embossed Klark Tall Boots from Villa Rouge ($275).
See All Jessica Simpson Outfits