How do you wear the one shoe that’s the most comfortable but also the least stylish?
That’s the question millions of women ask themselves every day. Some eventually crack it. Others just give up and reach for another shoe instead.
If you’re here, it means you’re still figuring it out, and that’s exactly what I want to help with.
I’ve spent time observing women in Milan, hunting for sneaker outfits that actually work. It wasn’t easy, but I pulled together 20 looks to inspire you. These are proof that you can wear sneakers and still have that effortlessly chic, put-together style Italian women are known for.
If they can make trainers look this polished, so can you.
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Sneakers With Skirts
Since we’re moving into the end of Summer, let’s talk about an outfit that works great for that, especially if you’re going on a trip.
This outfit is what most of us look for when travelling – comfortable but chic, lightweight but layerable, ageless, and easy to make yours.
It’s also the perfect answer to all of those looking for ways to style sneakers with skirts.
Shop White Sneakers
Tips for styling sneakers with skirts:
- Start with casual tailored pieces like a linen shirt or a more structured skirt.
- Keep the outfit and the layers simple.
- Opt for either white or skin color sneakers.
- Choose less bulky styles, especially if you’re petite.
- If you’re short, you might want to wear a shorter skirt with straight silhouette.
- Keeping a tonal outfit can also make the look put together.
Sneakers with Sets & Suits
Let’s dig deeper into that tonal tip I just shared with you. Monochrome outfits instantly make you look more dressed up because they create cohesion, and that looks chicer and more put together.
When you add the tailoring element to all of that you get the suit effect, which is probably exactly why these are so popular for work and business.
Nowadays, we’re also wearing them more casually, and that’s where sneakers find their perfect role. When you wear sneakers with a set or a suit, you immediately shift the tone of the outfit from serious to casual, from work to play.
This balance creates a very casual chic outfit, and that’s exactly why Italian women love wearing sneakers this way so much, way more than with skirts and dresses. This also explains why this section has so many examples, because I kept spotting them. So let’s see them.
We’re starting with the sleeveless linen option, because it’s the perfect season to wear this. Whether you’re going on one last Summer vacation or a warm fall trip, or have a more casual work environment, or want to wear sneakers to work and then swap into heels. Of course, these outfits also work for the weekend, if you love this vibe.
The next one is the perfect burnt orange set for fall, again in linen. We’re seeing the top part tied around the woman’s waist. While I can’t see it, I’d guess that’s a shacket style. Italian women love layering these over a white shirt. You’re essentially getting a double shirt moment.
The pink suit is what most people stop at when they’re trying the casual suit with sneakers. They take a more casual suit, in a light fabric and with a pop of color, and pair it with white sneakers and a simple t-shirt. It could be white or it could be in the same color family. If you’re going to go this route, just make sure you’re adding in your personality through your outfit details: the fabric, the cut, the buttons, the bag, the shoes, the jewelry, a hat, or not. Otherwise, you risk looking like anyone else trying this very popular look.
This next outfit is the perfect example. The woman has chosen a casual silk suit in a unique print. Even though she’s styling it very similarly to the previous look, those details make the outfit stand out.
Sneakers With Dresses
How to wear sneakers with dresses is the most asked question, so let’s see how Italian women do it.
This happens to be a pregnant lady outfit, but you could easily wear this with no bump. It works for traveling or a day on your feet running errands. And if you’re a chic mom, you could also wear this to drive your kids around.
You’ve got a white cotton straight line dress paired with a lightweight black blazer and white sneakers. The woman has rolled up the sleeves and she’s wearing a minimalist black shoulder bag.
Jeans and Sneakers
Most people think that this is the easiest pairing. It can, however, also be the easiest to get wrong, because it’s the easiest to go underdressed, too casual, and sloppy.
I think looking at how Italian women do it will give you a good idea of the important anchor pieces a jeans and sneakers outfit needs.
PS: I am not saying that these sneaker outfits are perfect, or that I love them all. There are actually very few I like and would try to recreate. I am also aware that these won’t look the same on me because I am petite, though the right pair of sneakers might be the thing my wardrobe is missing.
Let’s start with the type of jeans and sneakers outfit I have tried myself while traveling. It’s a pair of wide leg jeans with a chunkier cooler sneaker, a tshirt tucked in and a blazer.
Shop Cool Milan Girl Sneakers
Here are my tips:
- The jeans shouldn’t be too long but definitely not cropped. It should cover most of the sneakers and be wide leg enough to fall over the shoe without bulging.
- Avoid tshirts that look too fitted; they don’t look as chic. Learn more about how to pick the right white tshirt here.
- The blazer should be a little oversized, with a tailored structure but a more casual vibe. Think your boyfriend’s blazer but the women’s version. Of course, it’s important it doesn’t swamp you.
- You can also wear this outfit with a shirt, as you can see in example 2.
- The bag can shift the tone of the outfit – tote for more casual or smaller top hand for more feminine.
All these tips also apply to a straight leg pair of jeans with the classic Italian crop. Here’s an outfit like that. This woman is even showing the white socks and it still works.
Next, is a pair of white jeans. This is a great travel or casual outfit. The utilitarian jacket over the classic blue shirt makes it feel comfortable but put together. Without that shirt, the vibe would shift completely. The structured bucket bag is doing two things: adding more structure to the outfit and also adding personality. It’s not your usual tote bag!
Shop Italian Designer Sneakers
Finally, I’d like to show you an outfit that makes me cringe, not because it’s a bad one but because it has fringes. And that’s coming from someone who begged her parents to buy her this tan suede skirt and vest set that was so expensive and came with fringes. I was under 7 and that was very out of character for me but it still makes me laugh.
Do you like fringes and how much is too much for you?
Would you wear this?
Aside from the fact that I really don’t like that jacket and the sneakers color, let’s look at why this outfit works.
- The jeans have the perfect cut.
- The jacket has a good height and width when paired with those jeans.
- That ankle crop is the element that saves this outfit from looking out of balance.
- The platform element works in this case, and so do those socks. It helps that they fit the beige color palette.
Gorgeous Suede Sneakers
Sneakers With Cropped Pants
Want to know which clothing pieces I think make dressing up sneakers easy?
You guessed it.. It’s cropped pants, but also blazers.
If you pair them together, you’ve got a great outfit.
In this section, we’re looking at how Milanese women style their cropped pants with sneakers.
Let’s start with my favorite. It’s an end of fall, early Winter outfit, when you can endure having your ankle out. It’s tonal and feels very chic. You could wear this on a trip, especially near the mountains, though it works equally well for a casual city life day.
The next one is clearly being worn on an errand day. In fact, the woman is carrying her pets in a carrier bag, likely going to the vet.
Outfit three features a very interesting shacket with fur elements.
And the final one shows a chic woman over 50 wearing cropped pants with sneakers.
What do all 4 have in common?
- Tailored cropped pants that fit perfectly and have the right crop height.
- Designer sneakers that don’t look sloppy.
- A well thought out color palette.
- In some cases, a nice bag that elevates the entire look.
- And most importantly, structure on top. Whether it’a shorter or longer jacket, a shacket or a blouse, they all have some structure, and that makes the outfit look dressier, which in turn balances the casual shoes.
Sneakers With Wide Leg Pants
Finally, I’d like us to look at more sneaker outfits featuring wide leg pants. I have already shown you two with jeans.
Let’s start with my favorite. It’s a classic blue and striped blue outfit with dramatic sleeves (I’m not so keen on those, but it works) and a very wide leg silhouette.
It’s exactly that wide leg that makes the outfit look dressier than it is, and even suitable for work. And that’s because the pants are covering most of the sneakers.
This gives you a very practical solution if you’re someone who really dislikes this shoe. Hide them under palazzo pants.
The next two looks both feature leather but they are very different. One is very chic and dressy. The other is more casual and lived in. Both are tonal with a contrast leather jacket.
In both cases, the leather jacket dresses things up. However, in the second one it feels less so, and it’s because of the type of leather and the cut of the jacket.
The top choice also matters. A button up dresses up the outfit, while the roll neck makes it look more casual.
Can you see how it’s not just about the sneakers?
If you choose everything else to look put together and dressy, even your sneakers can feel that way. Obviously, they won’t ever give the look a heel would, but you get my point.
Finally, let’s see two more casual outfits and have a more relaxed airy top part.
Neither of them has much definition going on. There’s no clearly cinched in waist, there’s no ankle crop, but there’s still something to balance each.
For the first one, it’s the open shirt collar that shows a lot of skin, helping avoid the outfit feeling like it’s swamping the woman, and also adding femininity. The fact that the pants have a minimal wide leg also helps.
For the over 50 look, it’s the tapered waist detail in the jacket and the scarf that make it look more put together and add that definition we’re missing from all these generous layers.
More Italian Style Inspo
So, did you find an outfit formula or two that might make sneaker outfits work for you?
I hope this truly helps you put together that sneaker outfit you have been struggling with, whether it’s for a vacation you’ve got coming up, or a casual day with the family.
If you’re still not sold, or would like another casual shoe option, consider loafers.
Read this next: How To Style Loafers Like An Italian Woman: 35 Outfit Ideas
For more casual chic style inspiration, check out these other guides:
15 Blue Jeans Outfits From Milan – Effortless & Chic
How To Style A White Shirt Like An Italian Woman
11 Ways Italian Women Wear Comfy Fall Outfits
How To Style A White T-shirt The Italian Way
If you’d like to chat directly with me about Italian fashion, life, travel, and food, come join my Italian newsletter – Buona Settimana. I send one email every Sunday and it’s the best way for us to connect. You can join through one of the boxes on this page.
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A presto,
Alessia
