One of fashion’s “big four”, Milan is easily one of the most stylish cities in the world. Home to the biannual Milan Fashion Week and major fashion houses including Gucci, Versace, Dolce and Gabbana and Armani, there’s no shortage of style inspiration to be found in the vibrant Italian city.
Thanks to its rich manufacturing history, Milan emerged as a leader in ready-to-wear fashion in the 1970s and Milanese fashion became synonymous with elegance and practicality, with a strong focus on craftsmanship. This legacy lives on to this day, and some of the best looks during Milan Fashion Week can be found off the runway and on the city’s streets.
Here we look at the best Milan street style looks from across the years, ranging from quirky trend-led ensembles to pieces made up of capsule wardrobe staples.
The best Milan street style from across the years
Tortoiseshell and tan
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Brown has never exactly been out of fashion, but it’s had a renaissance in the last few years. The neutral shade is incredibly versatile and pairs well with a huge range of tones, but it also looks brilliant with other shades of brown. By mixing shades and patterns, this look feels super cohesive but interesting.
Sheer details
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A surprisingly wearable piece, an organza skirt can be worn over a slip or slinky top in the evening for a sophisticated look, or styled with casual pieces during the day. The white tank top and oversized white shirt inject a bit of casual flair into this look.
Paint the town red
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If you can’t wear a pair of statement shoes during Milan Fashion Week, then when can you? We love this head-to-toe red Ferragamo look from fashion blogger Leonie Hanne. By opting for different red and burgundy tones, the outfit feels super directional and the complementary colour scheme ensures attention isn’t pulled from her fringed shoes.
Keeping it classy
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Keeping it understated in an elegant black maxi dress, chef and writer Sophia Roe proves that sometimes less is more. Simple silvery jewellery and classic black sunglasses give this look a refined, polished finish.
A swish moment
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Unsure how to style black tights during those transitional months? Then take style notes from one of Milan’s most iconic fashion fixtures, Tamu McPherson. Her pleated black and white maxi dress pairs beautifully with a pair of sheer black tights and classic heels for an elegant, minimalistic outfit that makes maximum impact, without feeling fussy or complicated.
True blue
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In the sea of black sunglasses spotted at every fashion week, you’d be mistaken for thinking it’s part of the uniform. That’s what we love so much about these blue sunglasses; they completely transform this outfit from a classic evening look to something a little more kooky.
Wear your greens
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If you have a statement coat like this fabulous oversized Ferragamo leather trench coat, then you really don’t need much additional styling. By pairing it with a dark brown headscarf, black boots and a bag, this statement outfit looks super impactful without feeling too OTT.
Statement skirt
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Maxi skirts are a great capsule wardrobe staple, whatever the season. In summer, they pair beautifully with fitted tank tops or a boxy t-shirt, in spring and autumn, all you need is a fine knit or blazer, and in winter, team them with a heavier knit and trench coat. We love the feathered details on this one, which add an unconventional edge to a classic outfit formula.
An enviable ‘blazer and jeans’ look
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This look from Attico co-founder and creative director Giorgia Tordini shows the importance of investing in a few great staple pieces. In essence, it’s just a pair of great-fitting jeans, a classic blazer and an everyday white t-shirt. But as we all know, finding those pieces is much harder than it sounds, as the fit is everything.
Layers of polka dot
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Polka dots are a classic print, but that doesn’t mean they need to be styled traditionally. This layered polka dot top brings together an abstract design with a classic black-and-white print underneath for a quirky-but-chic look.
Sleek staples
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This all-black look from fashion designer Anastasja Trajkovska contrasts beautifully with her ash-blonde hair and proves that – when done right – black outfits are anything but boring.
If you find yourself struggling to style wide-leg trousers, then take notes from Trajkovska; her belt and fitted polo-neck add definition, while her elegant black heels gently lift her trouser hems from the ground.
An edgy lace look
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Mesh and lace materials don’t always see much daylight as they’re often reserved for evening wear. But they’re actually really easy to style for a cool but ultra-feminine daytime look. A knitted jumper, boxy t-shirt or casual leather jacket will create an effortlessly cool look that still feels quite special.
Suited in green
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On paper, a green leather suit sounds like a tricky outfit to pull off. However, the fitted blazer, straight-leg trousers and bottle-green colour make for a fabulously coordinated look that is making us green-eyed with envy.
A leopard print moment
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For some, fashion week provides an opportunity to pull out all the stops and to step out in statement pieces that otherwise don’t get much of an airing. However, sometimes simple (and ultra-wearable looks) can be just as impactful – like this classic leopard-print A-line skirt and black leather jacket.
Structured silhouette
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This navy blue outfit from Vogue vintage shopping columnist Jenny Walton is delightfully minimalistic, but her maxi-length peplum skirt gives it a beautiful silhouette. A short navy knitted tank top and leather bag complete the co-ordinated look.
Mix and match
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Stylist Nina Suess plays with texture and print in this layered ensemble, combining a silky beige slip dress with an oversized checked blazer. Her mesh flats and oversized sunglasses add an effortlessly cool edge, while also making it feel more directional.
Fringe appeal
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We adore this playful but glam outfit from model and influencer Livia Nunes Marques. Her brown oversized belted Ferragamo jacket adds a relaxed touch to her deep red tasselled Ferragamo maxi dress and towering olive-coloured heels.
Pillarbox red
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This all-red ensemble isn’t for shrinking violets but we love how vibrant it is. While it’s a bit ‘out there’, the red turtleneck, trousers, coat and shoes are all the same hue, making it perfectly harmonious and cohesive.
A timeless combo
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No one does smart-classic quite like the ladies of Milan, who often favour chic, well-tailored basics and thoughtful accessories for a glamourous look, rather than the urban aesthetic seen in New York.
Case in point, this ultra-chic all-navy look, complete with a pair of elegant cream heels. It’s timeless, and polished and every detail is on point.
Back to front
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An easy but often-overlooked styling hack, consider wearing your garms backwards for a completely different look. By styling this blazer back to front, it becomes a completely different piece, with a unique neckline and silhouette. A silk scarf cinches in the waist and makes it feel directional.
Daytime denim
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One of our favourite over 40 fashion bloggers, Grece Ghanem is a regular fixture at international fashion weeks where she’s often snapped in bold get-ups and playful yet glam ensembles. And this look is no exception; we love the unexpected pairing of a strapless denim dress with a white shirt. Her buttercup-yellow Bottega Veneta bag is also giving us serious envy.
Collegiate style – with twist
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No longer the preserve of high school footballers and jocks, varsity jackets have had something of a resurgence over the last few years. We’re taking style notes from one of Instagram’s most stylish women, Renia Jazz, who has slung hers over a checked midi skirt, fitted tank and some super fun fluffy black heels.
Statement gold jewellery
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Fashion trends come and go, but you can never go wrong with a navy-and-gold combo. Like so many great Milanese looks, this outfit brings together classic cuts with thoughtful accessories – in this case, gold earrings, a statement necklace and mixed metal bracelets.
All-ochre
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A silky maxi skirt and oversized knit are easily one of our favourite outfit combinations – particularly when they’re in matching tones. This look from model and influencer Tatyana Kodzayeva strikes the perfect balance between polished and cosy.
A lush minimalist look
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This classic Jil Sander co-ord oozes quiet luxury, with its clean silhouette, lush green colour and sophisticated cut. Minimal accessories and a slicked-back ‘do give an effortless edge to the look.
Dopamine dressing
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Bringing a burst of sunshine to a grey September day, this fabulous orange mesh dress is delightfully maximalist. Eschewing rules about how clothes are supposed to be worn, this fashionable street styler has opted to wear the dress open, with a pair of olive-green wide-legged trousers.
Denim and florals
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A relaxed co-ord set, made up of a top and trousers, can be tricky to style – often veering into pyjama or uniform territory if they’re not carefully put together. Here, the oversized denim jacket and platform boots add a bit of edge and elevate the look into something special and fashion week-ready.
Back to basics
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A classic black trouser suit is one of the most hard-working pieces you can have in your wardrobe. Appropriate for just about any occasion, the separates can be easily dressed up or down or adapted for the occasion. Here, an oversized brown jacket adds an effortlessly laid-back edge, creating an interesting, relaxed silhouette.
Sparkly sunnies
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These embellished brown sunglasses and shiny pink heels inject a bit of bling into an otherwise classic outfit, comprised of a slouchy burgundy knitted jumper and burnt orange skirt.
Socks and heels
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Filipino actress Heart Evangelista shows how dopamine dressing should be done with this vibrant red, grey and purple outfit. Her socks-and-heels combo adds an unfussy, modern touch.
A boho city look
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This look isn’t your typical Milanese style; the frills and wide-leg jeans give off a more boho vibe, leaning away from the sleek, city-dweller aesthetic. That’s not to say we don’t love it though – just look at those ruffles and the delicate gold accessories!
A statement bag
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We love Angela Rozas’s choice of accessories here; the oversized green Philosophy bag, knee-high socks and bow-adorned shoes elevate the classic grey dropped midi dress into something a little more quirky.
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