You’ve come looking for old money summer outfits because you love the aesthetic and want to dress that way, maybe you already do.
That’s perfectly fine, and that’s exactly the inspiration I am going to provide you with in this post.
But I also think we can take things a step further.
Hello and welcome. I’m Alessia, the writer and founder behind Italy with an Italian.
In addition to sharing 20 gorgeous outfits inspired by Milan’s Summer street style, I’d also like to challenge you to do more than simply recreate a quiet luxury aesthetic.
Keep reading if you’re intrigued.
Table of Contents
The Best Old Money Summer Outfits Spotted In Milan
A good way to start this interesting conversation is to answer this common question – what is old money style?
Ask yourself first, and answer it. Then, read my answer.
The way you perceive old money really matters, because it clearly indicates why you like it, and that’s something you always want to lean into when working on your personal style.
To me old money style is more than just an aesthetic, and that’s precisely why I want to start this more deeper conversation than just finding and copying the best old money outfits online.
When you see someone walking in Milan and you immediately think she looks old money, what do you actually see?
This is what I see:
- a beautiful woman, not just because she looks beautiful but because she carries herself beautifully. There’s a key difference!
- a confident woman, but it’s more of an inner confidence than a bold in your face energy. There’s nothing bold about the old money aesthetic.
- an outfit that looks curated but not overdone; it truly embodies the effortless chic element of Italian style.
- a woman that looks expensive, and it’s not necessarily because she is wearing expensive brands.
Let’s see the outfits that woman could be wearing. And remember that woman could be you, but it’s not just about recreating the same look!
Why Old Money Is More Than Just Style?
If your next question is what would I wear these outfits for, my answer is that it doesn’t really matter.
Real old money women don’t just dress that way to go shopping or to a fancy restaurant. They do it every day, whether they are going to work or grocery shopping. Many of them put on a chic outfit even when they are at home.
This is how you want to start thinking if you want to embrace more than just the temporary outfit aesthetic of this timeless style.
Here’s the challenge I hinted to in my intro: rather than just striving to recreate old money outfits why don’t you try to embody the typical old money woman.
When I explained what I think an old money woman looks like, did you notice I focused on these more than on her outfit:
- she carries herself beautifully
- she has natural grace and elegance
- she is confident but also feminine
If I go one step further, and think about what she would sound like, I can imagine her having a soft confident voice, be well spoken, well educated and cultured. She has interesting hobbies, and probably a well defined set of skills or career path.
And while that is certainly partly thanks to the fortunate financial position she was born into, that doesn’t mean you can’t get there without that.
Let’s continue seeing the outfits, and we’ll keep chatting about it.
How To Embody An Old Money Woman
I know that’s probably more than what you came here for, but you can take it just as food for thought, especially if you really love that aesthetic beyond the outfit but also the whole lifestyle aspect.
The easiest way to wrap your head around what I am telling you is this: if you embody her even just a little, you will find it so much easier to create the same type of outfits she would.
And it’s not about the outfits alone..
Imagine copying this next outfit, and then having a tacky phone case, or pretty charm bracelets, or braided hair. Can you see how that would go against the aesthetic?
That’s why thinking like her is going to make it so much easier, because you will also be curating the right hairstyle, makeup look, jewellery, etc.
I don’t want you to think you have to change yourself to look old money, far from it. I actually think you like the old money look because it looks sophisticated but in a very effortless and modern way. And that sophistication starts before the outfit.
Old Money But Colorful
These outfits all match the classic old money color palette we’re used to – the whites and creams, the dark colors, the brown, beige, and blues. It’s all very soft, and when there’s contrast it’s a clean one.
I’d like to challenge that and show you how adding a little bit of color can still feel quiet luxury, if you focus on ticking all the other boxes.
Do you agree?
Old Money Summer Outfits For Men
If your partner shares the love for this aesthetic, or maybe you’re the one styling him, I’d like to leave you with four outfit ideas for him.
All I said for the woman applies to men too.
It might just be gold instead of tennis, when it comes to those hobbies..
More Timeless Sophisticated Fashion Inspiration
This is not my first old money styling guide. I am really proud of my other one, and you can find a lot of great outfit ideas there. Go check it out:
20 Italian Old Money Outfits You’ll Love
Most of my fashion guides will include various old money outfit ideas, but I think you’re going to really enjoy these ones I have selected for you:
How To Style A White Shirt Like An Italian Woman
Travel Outfits For Women Over 50
Blazer Outfits For Women You Can Wear Beyond The Office
And if you’d like to build the kind of closet that’s at the basis of every old money Italian woman, start here:
Tailored Style Explained: The Italian Way To Dress Chic
Italian Women Style: 20 Pieces To Dress Like An Italian Woman
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Thank you for reading. Please give this a heart and share it with your friends.
A presto,
Alessia
