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How To Master Milan Style

21 September 2023
by Natasha Wynnyk
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Everything you need to know about how to dress in Italy’s fashion capital.

Milan is a place where fashion isn’t just a hobby, but a way of life. To navigate the sartorial aspects of the city, we turned to our team's creative powerhouse, Natasha, whose effortlessly-cool taste and trendsetting style make her the perfect person to give a bit of fashion advice. Join us as she shares her insider tips on packing and what to wear in this high-end destination.

Before I even visited Milan for the first time, I knew I was going to love it - and being there only confirmed my intuition. Not only is it a mecca for those who love fashion and design, but it has such a vibrant youthful energy. I loved perusing all the little boutiques and shops, knowing that everything the trendsetters were wearing in Milan were likely all the things I’d see people wearing back in the US in a few months. Even sitting for a glass of wine and people-watching is an inspirational fashion activity in itself in Milan.

If you want to fit in with the fashion-forward folks of the city, abide by these tips.


1. Embrace the Italian dress code with elevated everyday basics.

In Milan, fashion is a language spoken by everyone, anytime, anywhere. Italians have mastered the art of dressing up and dressing for the season, whether it's morning, noon, or night. Don't be afraid to step up your game and embrace the elevated aesthetic of Milan.



2. Rethink your pants game.

Jeans are perfectly acceptable in Milan for a casual look, but to make it a bit more refined, opt for non-ripped versions. Pair your jeans with an over-sized blazer or leather jacket to get that effortlessly chic look.

I also love to embrace different silhouettes, like these wide-leg trousers from Aritzia, or these Dr. Denim Wide Leg JeansPair them with a basic tee or tank top (I also love to throw in a stripe!) and then accent the entire look with jewelry. I love to do a chunky gold necklace (option 2) and gold earrings (option 2). I also always wear delicate rings and a few delicate bracelets. These small touches add so much to an outfit.


Aritzia Wide Leg Trousers


3. The shorts conundrum.

Calling all guys! While warm weather may tempt you to don a pair of shorts, take a cue from Italian men who usually opt for trousers, even during scorching summers. If you're set on wearing shorts, choose a more tailored and structured pair.

Everlane Performance Chino


4. The magic of a statement jacket.

A versatile item like an oversized blazer or a leather jacket can elevate any outfit in Milan. I’ve also been into leather blazers lately and this leather shirt jacket goes with almost every outfit. Throw one of these options over a simple dress, a jeans-and-tee combo, or even a jumpsuit. Play with the silhouettes- if you accentuate your waist with wide-legged high-waisted pants, then play around with doing a tighter top and pair it all with an oversized jacket. The addition of a statement jacket instantly adds a touch of refinement and sophistication.


GRLFRND Oversized Leather Bomber


5. Complete the fit with a statement purse.

I love to do a simple outfit- like a wide-legged trouser and white t-shirt- and tie it all together with a purse. I have this one from APC and I love it. It’s dark green and always gets a ton of compliments. The structure of it helps pull together a more loose fitting outfit. Reformation also just launched a line of bags and they're so cute. Loving this one

Reformation Mini Chiara Convertible Bag


6. Fashion forward footwear.

Footwear is crucial to completing your Milanese look. Opt for chunky heeled or lug sole boots or moto boots to effortlessly elevate your outfit, or a chunky sneaker. During the warmer months, leave the flip flops behind and embrace a a chunky loafer.


Reebok White & Green Club C Sneakers


7. More accessories? Why not!

I always bring multiple pairs of sunglasses on any trip to Italy. For me, sunglasses are the final touch and really define the whole outfit. Crap Eyewear has a ton of trendy options, but I also recommend perusing vintage stores around Milan for some unique options (that goes for bags as well!)


Crap Eyewear Supa Phreek Sunglasses


Milan is the epicenter of fashion in Italy, where the boldest style statements find their home. This is the time to pull out all those pieces from your closet that feel daring, but you never wear. In this city, there are no limits to expressing your personal style. Step it up with an oversized suit or go for a full monochromatic look. Always wanted to dress in all pink? Now is the time to do it!



From opting for refined denim to donning statement jackets and stylish footwear, these tips will help you navigate the fashion capital with confidence and style. So pack your bags, embrace the allure of Milan, and prepare to make some statements!


1 comment

  • Author's avatar image
    Lisa G Moss - Jun 19

    I want to know which stores are the best for the following, Leather clothing and purses, Clothing of all kinds, Silver picture frames and tea sets, etc; the best shoes, winter coats, Laser cut leather items, Jewelry finds, 18 carat gold. Glassware, and venetian chandeliers.

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