What Streetwear Guys Are Wearing in Milan

Milan’s streetwear style is bold, layered, and steeped in luxury. You’ll see classic tailoring mixed with cutting-edge sneakers, statement outerwear, and premium basics. It’s less hype, more refinement—with strong silhouettes and designer heritage front and centre. Here’s what Milan’s best-dressed guys are wearing on the street right now, and how to match the look with the right fit using Tellar.co.uk.

1. Tailored Jackets Over Track Sets

• Look for: Oversized blazers layered over knit sets or techwear

• Brands: Fear of God, Our Legacy, JW Anderson

2. Luxe Logo Bombers

• Look for: Monogrammed puffers, varsity jackets, MA-1 cuts

• Brands: AMIRI, Moncler, Balmain

3. Designer Denim + Chelsea Boots

• Look for: Slim jeans, stacked hems, Western stitching

• Brands: Rick Owens, Represent, Dsquared2

4. Soft Tailoring + Streetwear Tees

• Look for: Double-pleated trousers with streetwear branding layered underneath

• Brands: AMI Paris, Palace, Off-White

5. Bucket Hats, Loafers & Unexpected Mixes

• Look for: Accessories like shoulder bags, oversized scarves, leather accents

• Brands: Jacquemus, Kenzo, Prada

6. Smart Layering Meets Statement Cuts

• Look for: Collared shirts under cropped bombers, hoodies under wool coats

• Brands: Marni, Fendi, Zegna

How to Get the Milan Fit Right with Tellar

Luxury streetwear cuts vary by brand. Tellar.co.uk gives you accurate sizing for both oversized and structured silhouettes.

1. Enter chest, waist, hips—or a brand you already wear

2. See real-time size results in AMIRI, Moncler, Prada & more

Try it now: Tellar Store Size LookupNeed help? Men’s Measuring Guide

More Fit Tips from the Tellar Fashion Hub

• Best Jeans Brands

• Smart, Casual & Comfortable

Final Word

Milanese streetwear is fearless, polished, and layered with intent. Whether you're in denim or wool, Tellar.co.uk helps you size every piece to perfection—no guesswork, no returns.

Find your size in 1,500+ brands real-time. It’s free & easy.