7 shirt and jeans outfits that are far from boring

Every generation seems to go through a rite of passage where they “discover” trends—like the classic shirt and jeans combo—and ideas already recognized by those who came before them. Among these, fashion is a particularly vulnerable area. The entire fashion trend cycle can often feel like a long exercise in collective forgetfulness. So, let’s take a moment to acknowledge that the outfit formula that fashion experts claim will be the trend for spring 2025 is neither original nor new. It is not particularly interesting or, as Miranda Priestly would put it, “groundbreaking.” However, perhaps that lack of originality is precisely what makes it appealing.

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Yes, a shirt and jeans broke the internet when Kate Moss traversed the runway for Bottega Veneta’s Spring/Summer 2023 show. And yes, Charli XCX may have donned a striped shirt and skinny jeans for her big Billboard shoot in 2024. But they did so because this simple pairing has a long-standing pedigree in the It-girl’s wardrobe.

In the ’70s, it was the Jane Birkins and Farrah Fawcetts who put the nonchalant pairing through its paces, opting for free-loving flares and slim-fitting shirts. Fast forward to the ’90s, and it was Naomi Campbell, Princess Diana, and Cindy Crawford who repped double denim and waist-cinching silhouettes with their dashing-through-the-airport style. Then, in the Noughties, we flipped back to flares—except this time they came with pubic bone-grazing waistbands, boho button-ups, and ballet pumps. Kate Moss, we salute you.

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For 2025? Oversized is king. This fashion week, off-duty models and fashion editors alike sported oversized, corporate-coded shirting that looked like it had been swiped from a junior associate at JP Morgan. The colours? Crisp whites, pale pinks, classic stripes, and city-boy blues reigned supreme.

Denim-wise, despite fashion’s ongoing attempts to (re)discover skinny jeans, it’s clear the mantra remains: the baggier, the better. But whatever you do, skip the heels—take your cues from the ’90s jet-setting supers and stick to low-key flats like sneakers, loafers, or ballet pumps. Less Posh and Becks, more Sofia Coppola.

Silhouettes may shift and colourways come and go, but in its purest form, a shirt and jeans is the so-basic-it’s-brilliant outfit pairing that has become a gold standard for a reason. And as they say—if it ain’t broke…