Style Stories: from Rome to Milan & Lake Como

Italy is synonymous with rich history, world-class fashion, and an unmistakable allure that you can’t simply put into words. For my birthday this year, I had the pleasure of soaking up every bit of its magic. Italian style is renowned for its deep roots in craftsmanship, style and elegance, blending centuries-old traditions from the Renaissance with modern, avant-garde fashion – they are the innovators of elegant chic. When planning “What to Wear’ for this trip, I knew I wanted to stay true to my style, but also dress appropriately for each city I was in. Because after all, what is Italy without a few looks to match its amazing scenery?

Roman Romance: Classy and Sexy

Rome, with its ancient ruins and grand piazzas, inspired a look that whispered classic elegance. This year is all about ‘giving myself my flowers’, and I’m obsessed with roses – which inspired this look for a night out on the town in Rome. I previously purchased this dress from SHEIN, and was just waiting for the perfect moment to bring her to life. I paired this with my favorite black sandals from Kurt Geiger (theee most comfortable designer heels) and paired it with an early birthday gift: this beautiful bag from Jacquemeus.

This was perfect for our night out in Rome, where we enjoyed pasta from Osteria: a MUST try restaurant in Rome, ending the night at a Hookah Bar my boyfriend found – it was a vibeee.

This was actually one of my favorite looks, nothing like feeling sexy, full with amazing food, and drunk off the best Italian wine with the love of your life.

Milan & Lake Como: Old and New Money

In contrast, Lake Como called for something soft and sophisticated, after all, it is an hour outside of the capital of high fashion. For our day trip from Milan to Lake Como, I opted for a simple A-line polka dot dress, paired with my favorite Dolce & Gabbana sandals (these hurt like HELLL when I first got them, but after breaking them in, I have to stop myself from wearing them so much), and the cutest white sunglasses I found in Mango when we were shopping in Milan. I can’t find this exact pair on their website, but I linked a similar brand below. And clearly, I also couldn’t get enough of my new Jacquemus handbag – so that completed the look, emphasizing Italy’s reputation for elevated and luxury design.

The Intersection of Classic and Contemporary

What I loved most about experiencing Rome, Milan and Lake Como through fashion was how the outfits spoke to the spirit of each city. Rome, with its ancient charm, called for a look with a timeless appeal. Milan, modern and buzzing with energy, invited a touch of avant-garde flair, while Lake Como inspired an effortlessly sophisticated style that mirrored its serene and luxurious atmosphere.

Both outfits, however, shared one thing: I was confident in them. When deciding what to wear, this is the NUMBER ONE FACTOR. I don’t care if your favorite influencer wore it and it was cute on her, ask yourself do YOU love it and do YOU feel good in it?

Italy definitely has a way of transforming how you see fashion—it’s a reminder that every piece you choose can be part of your own story. Whether walking along Rome’s historic cobblestones or Milan’s sleek streets, or soaking in the serene elegance of Lake Como’s lakeside – the right outfit is about owning who you are and expressing it boldly.

Have you ever visited a place that made you rethink your style? Tell me in the comments, and don’t forget to check out my Rome and Milan/Lake Como looks linked above!