The preppy trend in menswear is set to remain a dominant force for the next two years, supported by a renewed appetite for classic dressing and reinforced by the influence of designers such as Jonathan Anderson. As consumers continue to prioritise longevity, versatility and quality, preppy style is increasingly seen as a safe and relevant choice rather than a nostalgic throwback.

Rooted in Ivy League and American sportswear traditions, preppy fashion has long been defined by staples like button-down shirts, blazers, knit polos, chinos, loafers and cable-knit sweaters. In recent seasons, these pieces have returned with updated proportions, softer tailoring and more relaxed styling, making them feel current without losing their heritage appeal.

Jonathan Anderson’s growing presence in menswear has played a significant role in pushing the trend forward. Through his work at Dior Men and his broader cultural influence, Anderson has reframed preppy dressing as expressive and modern. His approach blends traditional tailoring with playful experimentation, mixing formal elements with casual details and unexpected styling choices. This balance has helped strip preppy fashion of its stiff reputation and reposition it as creative and fluid.

The impact of this shift is being felt across the industry. Luxury houses are increasingly embracing classic menswear codes, while contemporary and heritage brands alike are leaning into preppy aesthetics. Labels such as Brooks Brothers, J.Crew and J.Press, which are closely associated with Ivy style, are benefiting from renewed interest as shoppers rediscover timeless silhouettes and fabrics.

At the same time, these brands are adapting to changing consumer expectations. Fits are becoming looser, fabrics lighter and styling more flexible, allowing traditional pieces to work in casual, work and social settings. This evolution has helped preppy fashion appeal to younger consumers who value comfort and individuality alongside structure.

The trend is also being amplified by the broader return of tailoring, albeit in a softer form. Rather than rigid suits, today’s tailoring favours relaxed jackets, pleated trousers and layered looks that feel effortless. Preppy dressing naturally aligns with this movement, offering polished looks that do not feel overly formal.

Retail buyers have taken notice. Many are prioritising merchandise that can perform well across seasons and occasions, reducing reliance on fast-moving trends. Preppy staples fit neatly into this strategy, as they tend to have longer shelf lives and consistent demand. In an environment where brands are cautious about overproduction and markdowns, classic pieces provide greater commercial stability.

Economic uncertainty has also influenced the trend’s staying power. As consumers become more selective with spending, there is a growing preference for items that feel like investments. Preppy clothing, with its emphasis on durability and timeless design, meets this need. Shoppers are increasingly drawn to pieces they can wear repeatedly without feeling dated.

Cultural shifts have further softened the image of preppy fashion. Social media, film and television have reintroduced preppy visuals in more relaxed and inclusive ways. Styling now often mixes classic pieces with casual footwear, denim or streetwear elements, making the look feel approachable rather than exclusive.

Younger designers and brands are also contributing to the trend’s evolution. By borrowing preppy codes and reworking them through modern lenses, they are expanding its reach beyond traditional audiences. This cross-pollination has helped keep the style dynamic and relevant, rather than static or predictable.

Jonathan Anderson’s influence remains central to this momentum. His ability to bridge heritage and innovation has positioned him as a key tastemaker in menswear. By treating classic clothing as a foundation rather than a constraint, he has encouraged a more playful and open interpretation of preppy style.

Industry insiders expect this influence to continue shaping collections across both luxury and accessible price points. As more designers adopt similar approaches, preppy fashion is likely to remain visible on runways and in stores, reinforcing its position as a long-term trend rather than a short-lived revival.

From a strategic standpoint, the endurance of preppy style also reflects a wider recalibration within fashion. Brands are increasingly focused on building strong core offerings that can support growth over time. Preppy essentials, with their broad appeal and adaptability, are well suited to this goal.

Overall, the outlook for preppy menswear remains strong. With continued support from influential designers, evolving consumer tastes and favourable retail dynamics, the trend is expected to stay relevant for at least the next two years. Rather than fading, preppy fashion is settling into a new phase one that values tradition, but embraces change.