Ciao! With fashion turning its attention to the Italian sartorial capital for Milan Fashion Week, the birthplace of Prada and the Negroni Sbagliato has become a hotbed for impeccable street style. Within its ringed walls, local haunts like the Via Monte Napoleone and Palazzo del Senato have been transformed into runways in their own right.
Whilst it’s not unusual for the city’s natives to deliver a masterclass in everyday elegance—this is the place that pioneered dressing archetypes like the well-heeled and glamorous “sciura”, after all—the convergence of star-studded guests and incredibly sophisticated denizens have certainly dialled things up a notch. In fact, you could say that the outfits are nothing short of molto benne.
But given this is the place that hosts collection presentations from the likes of Fiorucci and Diesel, the one category that has piqued our interest the most has certainly been the denim. From dark blue Gucci Giglio tote bags to the ivory Bermuda shorts, denim of all varieties has been saturating the city faster than you could order an Aperol Spritz.
With this category being one of the most useful in any well-edited wardrobe, we thought it best to spotlight the notable looks that are actually wearable now and chronicle the key denim street style trends taking over Milan Fashion Week. Though the autumn/winter 2026 shows might be far more stirring in terms of what’s shown, it would be remiss of us to not to devote a little time to discussing the looks that are already turning heads.
From new washes approved by editors to the silhouettes adored by off-duty supermodels, keep scrolling through for the key denim trends defining Milan Fashion Week.
1. Upturned Cuffs
Style Notes: Take it from the best in the business. When needing to add an element of visual contrast, simply take the cuff of your jeans and turn it up a few inches. If it’s good enough for Bella Hadid—who achieved a major career milestone this week by walking Prada’s show four times—it’s good enough for me.
Shop the Trend:
Take the fuss out of styling with this pre-rolled option from Mango.
Damson Madder has quickly become London's go-to brand for anything-but-basic basics.
Pair with wardrobe staples like structured flats and weighty jackets.
2. Ultra-Baggy Silhouettes
Style Notes: The off-duty wardrobes of models have always served as inspiration. However, for those who pay close attention, you’ll notice that these ensembles are always the least flamboyant. Featuring practical details like oversized tote bags, functional flats and baggy denim that’s easy to slip in and out of backstage, you can always rely on this set to leave the more ostentatious displays to the collections themselves.
Shop the Trend:
Italian's might have a preference for the slim-cut cigarette trousers synonymous with Gucci and Giorgio Armani, but when the international crowd is in town, expect hemlines to get extra wide.
These jeans are so slouchy that they can double as a pleated wide-leg trouser, making them a perfect wardrobe for any editor or tastemaker who does the entire fashion month circuit. Because when you need to visit four cities in less than a month and with one checked bag, versatility is imperative.
Citizens of Humanity's Ayla jeans are one of the brand's best sellers because of their comfort, buttery soft feel and ultra-slouchy silhouette.
3. Stovepipe Shapes
Style Notes: The Carolyn Bessette Kennedy effect has hit Milan. Fashion people aren’t immune to the whims of popular culture, so it’s no surprise to see attendees taking a page out of the beloved fashion icon’s handbook and sauntering through the city in her preferred cut of jeans—stovepipe.
Shop the Trend:
The razor-sharp silhouette makes this style look incredibly sophisticated.
Whilst the Italians certainly have their merits, I personally can't overlook French denim.
Perfect proportions and fabrics are the cardinal rules of anything Catherine Holstein designs, meaning this style will be immaculate in both material and fit.
4. Barrel Legs
Style Notes: If the 1990s had razor-sharp shapes, then the 2020s have barrel legs. Slouchy through the thigh and tapered around the ankle, this horseshoe-esque silhouette injects a sculptural touch to outfits crafted from well-edited basics.
Shop the Trend:
So effortlessly elegant.
Slouchy enough to feel comfortable, structured enough to look chic.
You can just imagine how casually cool you'll appear trotting around in these.
5. Split Hemlines
Style Notes: The beauty of fashion week is being on the pulse of what’s to come next. Before collections hit boutiques, the style that’s displayed indicates the ways we will be dressing for months to come. Consider, then, split hem jeans to be the next frontier of denim. Despite this being a design element mostly relegated to trousers or ponte leggings, it’s refreshing to see this sliced edge being applied to your favourite pair of baby blues.
Shop the Trend:
Because why hide your boots away when you can show them off?
This style puddles around the floor so beautifully.
Blending Scandinavian simplicity with American attitude, this Anine Bing pair strikes the right chord.
6. Indigo Washes
Style Notes: We might finally have an answer for Leonard Cohen, who asked over a decade ago whether we wanted it darker. According to the Milan Fashion Week street style set, we do, with the chicest denim styles boasting a deep indigo wash. Featured on Khaite’s recent runway and the colour of the world’s first-ever pair of jeans designed by Levi’s all the way back 1873, as the weather warms, expect the dyes we wear to only get cooler.
Shop the Trend:
Deep tones will always look more considered, in my humble opinion.
High-waisted and wide-leg jeans are such a go-to silhouette for the fashion set.
There's not a white t-shirt or black blouse going that wouldn't pair nicely with this Agolde style.