If you stepped off the train at Piccadilly Station in London, you would find yourself in what is considered the birthplace of the modern loafer. According to one version, in the 1920s, Wildsmith Shoes created a pair of casual, buckle-less loafers for King George VI, a comfortable shoe for relaxing after a weekend of hunting. Within a few decades, loafers had become a favorite among everyone from Ivy League students to Manhattan financiers. By the 1990s, they had become a stylish, casual, and versatile everyday shoe.
Carolyn Bessette-Kennedy and John F. Kennedy Jr.
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In 2026, it's the 1990s-style loafers that are making a comeback. They're to this year what sneakers were to 2024 and ballet flats were to 2025: a shoe that goes with everything and everywhere. They're most often paired with straight-leg jeans or dress pants. Still, if you want to recreate the 90s aesthetic, you should turn to those who set the tone. Below are five ways to wear loafers from 90s style icons.
Preppy style
Sarah Jessica Parker
Focus on Sarah Jessica Parker from the early 1990s or the looks from the 1996 film “The Witcher.” However, you shouldn't copy this style literally – it's better to adapt it to modern times: a shorter skirt, a looser jacket, a less formal shirt, high socks, and loafers.
Bright color accent
Cameron Diaz
Colorful loafers are back in the spotlight this year. At Loewe's Spring/Summer 2026 collection, tomato-red, square-toed loafers were styled with a collarless leather jacket and little else. If you're not ready for such a bright shoe, opt for a more subdued option: a muted burgundy or olive green shade.
Classic straight jeans
Carolyn Bessette-Kennedy and John F. Kennedy Jr.
There's no need to explain the benefits of perfect straight jeans and classic loafers. Just watch the TV series “Love Story.” Carolyn Bessette-Kennedy wore this flawless combination in real life. Add a cashmere turtleneck or a white shirt to make the look work completely.
Suit
Cindy Crawford
Is there a more timeless look than a loose, baggy suit and a pair of loafers? In the 1990s, this combination was loved by Wall Street financiers and supermodel Cindy Crawford. In 2026, the baggy suit and loafers combination works for almost any situation: from a business lunch to a club.
Floral prints
Julia Roberts
To keep the look from looking too romantic, wear a floral dress with loafers, cotton socks, and small sunglasses. This way you’ll get a 1990s Julia Roberts look. If the floral print seems too cute for you, swap it for a plain mini dress. The loafers will still make the look sharper and more modern.
Based on material from vogue.co.uk