How to Dress With Intention in 2025

With examples from the masters of intentional style - the Milanese ;)

It’s 7:16AM here in Milan; it’s still dark. I’ve been asked to reflect on my time in Italy for another creator’s newsletter (I’ll let you know when the post goes up), and what I can conclude with absolute certainty is that Milan is elegant. I’ve always felt this, but the idea was underscored after spending two weeks in Rome over the holidays with family. Rome is colourful, it’s chaotic, and open. It exposes all parts of itself to you when you first meet; the good, the bad, the ancient. Milan keeps her cards close, and her style is always impeccable. Even in the winter.

Milanese style is direct, to the point. It’s thoughtful and sophisticated, whether trend-driven or not. And while we can find the best inspiration and the smartest styling tips; we won’t capture the essence of our style if we don’t know who we are and follow it with clarity and creativity. And consideration.

Ok that’s a lot of things but I like an alliteration.

Clothes are the visual part of the story that we tell ourselves. The sweet spot is when our internal and external narratives are aligned.

So in the spirit of a new calendar year, I’ve got some of my favourite style intentions to get you started. Think of them less as goals and more as guideposts if you’re feeling lost with your style or mindless in your shopping. These intentions may seem simple, but small tweaks add up to great change. Take what you need or create your own! These are some that my clients find most useful, and which we discuss in the community!

1 - develop a style routine: it doesn’t have to be complex. It could simply be to take a picture of your outfit before you leave the house so you have a bank of outfits to pull from when you’re stuck. I have a video that digs deeper into what a style routine looks like - even if you only have 5 minutes to spare in a day!

2 - develop a style identity: there are lots of ways to do this, and we are always changing - so nothing is set in stone! Helpful tools are descriptors like the 3 word method, but we can also dress with joy simply by knowing how we want to show up in life. What do we want to present to the world? This can look different every day, and it’s why I LOVE elements of style, because then our style isn’t prescribed to us by an item of clothing. Instead, our clothes become tools that we can manipulate to suit a mood or aesthetic we want to show. This video is an intro to this concept.

3 - determine and focus on your values: fashion has so many issues because it touches almost every other industry on the planet. So those industry issues become fashion’s issues. (think environment, fair labour, social justice, inclusion, animal welfare, plastics, fossil fuels, copyright, tech, the list goes ON). It is VERY easy to get overwhelmed. The best way to avoid overwhelm is to choose 3 to 4 values and shop with those in mind. I’ve been saying this for a while, but it’s always good to re-visit if we’ve been shopping with our values in mind or if they’ve changed.

4 - stay tidy: it’s simple, but keeping your closet and clothes organized, visible, and accessible will do wonders for your style. Maintaining it can be part of your style routine!

5 - practice gratitude: I’m a broken record here, but this small daily practice can help shift your mindset from one of scarcity to abundance. It can be as simple as making a mental list of 3 things you’re grateful for at the end of the day. What I love about this is that it affects every aspect of our lives.

6 - shop your closet: the intention here can be as simple as; “going forward, if i think i need to buy something or I want a new outfit, I’m going to check my closet first.” If you want help in this department, I have a Youtube Channel dedicated almost exclusively to the subject. I know shopping your closet is a trend now (YAY!) but here we’ve been at it since 2017 - so you have LOTS of examples in this playlist)

7 - maintenance: the way we take care of our clothes has a significant impact on their carbon footprint. The intention here can be as simple as; “I will take the time to mend (or take to a tailor/seamstress) or clean this properly instead of decluttering it”

When we do this legwork on the inside, our style benefits. Here are some examples of intentional dressing that I’ve found online and that I’ve snapped in real life from the masters of intentional dressers; the Milanese :)

At the market. This look feels easy but also pulled together. I love the intentionality behind the colour choices: tonal accessories to harmonize with the coat, and a dark classic shoe to offset the whole thing. I like how the black loafer adds definition through colour but also silhouette. This is a good kind of tension, and functional too!

℅; the OG of street style photography: The Sartorialist! Sneakers with tailored separates or elevated dresses are very common here, but I like how this gentleman made a very deliberate choice to make his sneakers stand out. What tells me it was deliberate is the size of the bag - it acts as a nice counterweight to the visual heft of the sneakers. This is what I mean when I talk about visual balance! It can be done with colour AND proportions.

I love a monochromatic look, and this one stood out to me. Dressing tonal in a colour that is not black takes consideration. I like the mix of textures and the layering - especially the turtleneck! It’s a great choice for an oversized and floufy collar. There’s no competing detail, and it allows the tonal palette to be the star. I also like the deliberate choice of a chunky boot which is another good counterweight to the voluminous coat. Balance again!

Another look from the Sartorialist in Milan. As simple as this look is, the shoe choice (it’s always about the shoes!!) is unexpected for a track pant, which makes this look thoughtful. It doesn’t feel overstyled - likely because of the loose silhouettes and functional bag. The tension in the shoe/pant combo is enough, you see? A perfect balance of intention / ease. Sometimes if we try too hard the whole look can feel forced!

Let me know what you thought of my first newsletter! I wanted to cover both the internal and external parts of style since you can’t have one without the other.

Thank you for being here!

Alyssa

xx