Advertisment

Milan Fashion Week: Best Street Style Looks From Outside The Menswear Shows

The first fashion week of the year is setting a fresh style precedent for the 12 months to come, when serving winter looks like these, it deserves some attention.

Milan fashion week

And just like that... the first fashion week of 2025 has arrived. Hot off the heels of the new year are the Milan Fashion Week shows presenting the AW25 menswear collections, with brands like Prada, Armani and Dolce & Gabbana on the schedule. Sure, there's much to glean from what's trending on the catwalk for our own wardrobes, but the offer is much richer for right here, right now with what's happening outdoors. Street style is back and there's a lot to take in.

From the stylish Milanese set to the fashion editors jetted in for a short, sharp visit, the trends that will go on to define 2025 are being presented here first along the Italian fashion capital's rather damp strade. Some have kept it top-to-toe for one singular designer whereas others have mixed things up so much so that odd shoes have even been spotted and, dare we say it, convincingly so. So, while we more than appreciate what's happening for the guys on the catwalk, it's the women attending the shows that are giving us the style inspiration we need to take on winter dressing with aplomb right now.

 

Milan Fashion Week Menswear Street Style A/W '25

1. Milan Fashion Week Menswear Street Style A/W 25

milan, italy january 19 a guest wears a grey coat with black fur applications, a light blue knitted turtle neck oversized sweater, a black skirt, a black leather bag and black leather knee high boots outside prada show during the milan fashion week menswear fallwinter 2025 2026 on january 19, 2025 in milan, italy photo by valentina frugiuelegetty images

An old favourite done a new way makes for a stylish shake-up,  like a classic Aran jumper in Yves Klein blue.

2. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

More proof that a classic pair of jeans never goes out of style.

3. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

Clever details like pinstripe jeans elevate a simple outfit combination.

4. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

White accessories make for a surprising, but valuable, winter wardrobe player.

5. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

Classic tailoring doubles in impact when worn layered.

6. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

A clash in textures is a fail-safe head-turning trick favoured by seasoned showgoers.

7. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

Immaculate execution played out in two different colourways.

 

8. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

Proof that no one formula works for every street-style star.

9. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

Functional trainers continue to be a fashion girl's favourite sneakers. 

10. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

A great coat - and sunglasses - will never go out of style.

11. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

In January, slouchy knitwear is always the answer. Note this colour combination and pay close attention to the socks, too. 

12. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

Returning to one's personal archive (Prada SS14 in ADR's case) is the latest fashion flex favoured by the style crowd.

13. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

An all-black background allows this Prada coat to sing.

14. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

A great padded coat is not just for winter walks through the local park. Take yours for a spin with a pencil skirt and pointed pumps.

15. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

The oversized blazer trend shows no sign of slipping away. And the same goes for Margiela Tabis, in whatever form.

16. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

A trench coat feels best at home when worn with a colour palette that leans into its autumn-like hue. 

17. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

Bright-coloured knits are a sure way to lift the spirits.

18. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

A voluminous pair of trousers with a natty jacket makes for an easy outfit proposition. Sky-high heels are optional.

19. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

Pink feels at its most peppy when set against January's obligatory dreary skies.

20. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

Intricate details go the distance when it comes to standout outerwear.

21. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

A voluminous winter coat not only makes a statement but allows for plenty of layers under.

22. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

Make the most of winter's cool temperatures by layering knitwear in interesting new ways.

23. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

A clever palette offers louche silhouettes a sharp execution.

24. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

Some things never change: the fashion still set loves an oversized coat.

25. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

How to do the bonnet the Milanese way. 

26. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

Can you? Would you? Will you try a mix-match shoe combination this season?

27. Milan Fashion Week Menswear Street Style A/W 25

milan fashion week street style outfits

An oversized menswear-style jacket offers the right amount of confident fashion discourse.

ELLE Collective is a new community of fashion, beauty and culture lovers. For access to exclusive content, events, inspiring advice from our Editors and industry experts, as well the opportunity to meet designers, thought-leaders and stylists, become a member today HERE.

Read the original article in ELLE UK.

Read more:

ELLE Exclusive: Onitsuka Tiger x Astro Boy 2.0 Is Here, We've Got The First Look!

Drip Check: Homegrown Sneaker Brands Redefining The Game

Related stories