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Kendall Jenner’s Striking Calvin Klein Shots Through The Years

Over the years, Kendall Jenner has redefined her image with a series of memorable Calvin Klein campaigns. From bold lingerie shoots that mix delicate textures with rugged elements to minimalist denim looks that capture the brand’s classic appeal, Jenner’s style choices reflect a dynamic evolution.

Her ability to balance softness with edge and elegance with simplicity showcases her versatility and keeps each campaign fresh and visually compelling.

These shoots not only highlight her as a model but also emphasize the distinct aesthetic that Calvin Klein is known for—effortless, modern, and captivating.

Lingerie Set, Paired With Rugged Boots

Image: Instagram/calvinklein

In these recent shots for Calvin Klein, Kendall Jenner embraced a bold, edgy aesthetic. With a fresh pixie cut, she modeled a black lace lingerie set, paired with rugged boots, sitting against a dark backdrop. The look highlighted an unexpected mix of delicate and rough, playing with textures and contrasts.

Kendall Jenner in sheer lace bralette with tailored black trousers
Image: Instagram/calvinklein

On the beach, she continued this theme, combining a sheer lace bralette with tailored black trousers and loafers. The ocean backdrop added a dramatic, windswept feel, amplifying the powerful, avant-garde mood of the shoot.

Relaxed Confidence (2015)

Kendall Jenner in black lingerie 2015

In the 2015 Calvin Klein campaign, Kendall Jenner embodied a relaxed confidence, captured in a simple yet striking black lace set. The soft texture of the lingerie complemented her natural, understated beauty, creating a look that was both intimate and powerful against the dramatic monochrome backdrop.

Candid Moment (2019)

Image: Instagram/calvinklein

In this 2019 Calvin Klein shoot, Kendall Jenner captured a laid-back, intimate vibe in a delicate black lingerie set. The soft lace detailing added a subtle elegance, while her relaxed pose and natural makeup highlighted her effortless, everyday charm.

Kendall Jenner looks sexy in Calvin Klein underwear
Image: Instagram/calvinklein

The structured design of the bra and the delicate detailing on the briefs balanced boldness with refinement.

Athletic Edge (2019)

Kendall Jenner in a vibrant red bralette with the iconic '1981 Calvin Klein' band
Image: Instagram/calvinklein

In this 2019 Calvin Klein campaign, Kendall Jenner sported a bold, sporty look featuring a vibrant red bralette with the iconic ‘1981 Calvin Klein’ band. The athletic style combined with her natural, soft gaze created a dynamic contrast, capturing both strength and simplicity.

Urban Edge (2019)

Kendall Jenner in monogrammed crop top and leggings set.
Image: Instagram/calvinklein

In this 2019 Calvin Klein campaign, Kendall Jenner embraced a bold, urban aesthetic in a monogrammed crop top and leggings set. The all-over logo pattern created a statement look, balanced by the sleek, modern vibe of her white ankle boots. Captured in the backseat of a car with neon lighting, the shot evoked a night-out-in-the-city feel, blending sophistication with an effortlessly cool attitude.

Relaxed Sporty Vibe (2019)

Kendall Jenner in red Calvin Klein bralette paired with matching briefs
Image: Instagram/calvinklein

In this 2019 Calvin Klein campaign, Kendall Jenner embraced a sporty and casual look, featuring a red bralette paired with matching briefs, both adorned with the classic Calvin Klein logo band.

Casual Cool In Calvin Klein (2019)

Kendall Jenner in 2019 Calvin Klein campaign
Image: Instagram/calvinklein

In this 2019 Calvin Klein campaign, Kendall Jenner lounged effortlessly in a printed bralette and briefs set, featuring a playful pattern with the iconic logo waistband.

Minimalist Denim Look (2023)

Kendall Jenner’s Minimalist Denim Look in Calvin Klein (2023)
Image: Instagram/calvinklein

In this 2023 Calvin Klein shoot, Kendall Jenner embraced a stripped-back, natural look, wearing only a denim jacket that subtly revealed her effortless style.

Kendall Jenner in sleek black lace lingerie set
Image: Instagram/calvinklein

For the same 2023 campaign, Kendall Jenner modeled a sleek black lace lingerie set. The minimalist styling and monochrome tones added an elevated, sophisticated edge, capturing her in a bold yet elegant pose. The lace details provided just the right amount of texture, complementing her confident, poised expression.

Bold Denim Look

Kendall Jenner’s Bold Denim Look for Calvin Klein
Image: Instagram/calvinklein

Sporting a denim jacket paired with high-waisted jeans, Kendall took on a bold, minimalist vibe in this 2023 shoot. The partially open jacket added an edge to the look, highlighting the brand’s focus on both comfort and daring style.

Cozy Vibes (2023)

Kendall Jenner in soft, gray bralette and matching brief
Image: Instagram/calvinklein

Kendall kept it casual and intimate in a soft, gray bralette and matching briefs, lounging comfortably in a relaxed setting.

Denim Confidence

Kendall Jenner wearing Denim Jacket
Image: Instagram/calvinklein

Posing in a denim ensemble, Kendall exuded confidence in this Calvin Klein shoot. The off-shoulder jacket and classic jeans emphasized her laid-back yet bold attitude, captured perfectly in a black-and-white frame that showcased the timeless appeal of denim.

Classic Calvin Klein Simplicity (2023)

Kendall Jenner in white tee paired with matching logo briefs
Image: Instagram/calvinklein

In this 2023 Calvin Klein shoot, Kendall Jenner embodied the brand’s iconic simplicity, wearing a classic white tee paired with matching logo briefs.

Sleek Black Dress

Kendall Jenner in a sleek black dress paired with cowboy boots
Image: Instagram/calvinklein

In this 2023 Calvin Klein shoot, Kendall Jenner embraced a modern Western-inspired look, featuring a sleek black dress paired with cowboy boots. The cutout detail of the dress added a touch of sophistication.

Power Suit Statement

Kendall Jenner goes bra less in power suit for official Calvin Klein campaign
Image: Instagram/calvinklein

Kendall redefined power dressing in this Calvin Klein campaign, modeling an oversized suit without a shirt underneath. The structured jacket and loose-fit trousers contrasted with her daring pose, showcasing both strength and vulnerability. The monochrome palette highlighted the modern edge of the look, blending elegance with a bold fashion statement.

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