Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants.

Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants.

      There are few outfit combinations that have the enduring appeal of cropped black trousers paired with minimal loafers. Recent images from the set of *American Love Story* have reminded me exactly why this pairing is so timeless. In freshly released photographs from the filming, Sarah Pidgeon, who plays Carolyn Bessette-Kennedy—one of the most captivating style icons of the '90s—displays a classic look: black cropped trousers, a black roll-neck top, and sleek black loafers, inspired by an outfit Bessette-Kennedy wore while in New York in 1995. It exemplifies '90s minimalism at its finest, and yet, it feels incredibly relevant today.

      In *American Love Story*, Sarah Pidgeon films scenes portraying Carolyn Bessette-Kennedy, an American fashion publicist and style icon known for her marriage to John F. Kennedy Jr. While the outfit draws from Bessette-Kennedy's iconic style, it remains popular among fashion enthusiasts today, and there’s a reason for its longevity. I believe it’s all about balance. Ballet flats, though chic and stylish, can occasionally feel too delicate when paired with sharply tailored black cropped trousers. Conversely, loafers provide the perfect amount of structure and weight, anchoring the overall look.

      Bessette-Kennedy (right) is seen in 1995 wearing a navy jumper, black cropped trousers, and black loafers in New York. Loafers inherently carry a certain elegance, especially when they feature a minimalistic design—no bulky soles or flashy embellishments, just clean lines and soft leather that hint at classic style. When teamed with black cropped trousers, the outcome is an effortlessly sophisticated and timeless appearance that has transcended three decades.

      Whether you're intentionally channeling Bessette-Kennedy or simply seeking a reliable outfit for both urban outings and evening events, this combination is difficult to critique. Keep scrolling to view and shop my selection of the chicest black cropped trousers and loafers available.

      **Shop Black Cropped Trousers and Sleek Loafers**

      - **ZARA**: Cropped Darted Trousers

       The wide-leg design offers these trousers a lovely sense of movement.

      - **Whistles**: Black Manny Slim Loafer

       The sleekest loafers I've found.

      - **Marks & Spencer**: Jersey Slim Fit Ankle Grazer Trousers

       If you prefer a straighter leg, this M&S pair is for you.

      - **Reformation**: Kat Soft Loafer

       Suede adds a stylish touch to this outfit.

      - **& Other Stories**: Slim Press-Crease Trousers

      - **M&S Collection**: Leather Loafers

       It's rare to find leather loafers in this price range, but M&S has succeeded.

      - **Whistles**: Black Camilla Wide Leg Trouser

       The high waist will replicate Bessette-Kennedy's original streamlined look.

      - **CHURCH'S**: Pembrey W Leather Loafers

       A top-tier loafer brand.

      - **Reiss**: Pintuck Tapered Trousers in Black

       These cigarette cropped trousers are also available in petite sizes.

      - **MANGO**: Straight-Cut Crop Trousers

       This style can be easily dressed up or down depending on your top choice.

      - **Anthropologie**: Intentionally Blank Pinky Loafers

       Give your loafers a fun twist by pairing them with white socks.

      - **COS**: Cropped Tailored Trousers

       COS consistently excels in tailoring.

      - **AEYDE**: Vanna Leather Loafers

       These loafers represent minimalism at its best.

Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants. Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants.

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Since the 1990s, the most stylish women have paired this shoe trend with cropped black pants.

And no, it's not ballet shoes.