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  • Writer's pictureSyd

An American Fashion Designer's Roman Holiday

What I wore, where I shopped, and what you're not going to want to miss!

Sustainable fashion designer Sydney Duncan in the stylish city of Rome, posing in front of the Trevi Fountain,

When I got the text that my dear friend Brenda, an Indian born women who I had met 5 years ago in Switzerland, would be returning to Europe just as I moved to Milan - it was certain that our friendship-long dream of visiting Rome together would become a realty...

and it did not disappoint!

Join me (and Brenda!) in our three days of exploring Rome's most stunning neighborhoods - from ancient ruins to alleyways brimming with vintage shops. I'll let you in on what to wear/not to wear to fit in with the locals (including Vatican City appropriate attire), show you where to shop sustainable and vintage fashion, and of course let you in on my favorite Gelateria!

First, a Quick Intro to Italian Style

Italian fashion at its peak is exactly what I had come to expect.

Women of Rome, similar to those of my new home of Milan, displayed a stunning collection of heirloom furs layered over neutral colors, prominent designer brands fitted from head to toe, well tailored and timeless. The most style conscious of the men were also groomed to a T, their hair freshly trimmed and gelled, long scarves tucked into structured wool coats, and feet cradled in high end leather shoes.

It is a fashion show on the streets - and an obvious flaunting of status. Though I'll admit, in a country so infatuated with designer this and designer that, I am finding it hard not to drink the kool-aid.

* I am not advocating for the modern day production of furs, leathers, unethical wool, etc. It's 2024, we can do better people!

Shoe: Form vs Function

While it is dangerously tempting to pack your chicest of stilettos, my advice is to avoid heels unless you have arranged for transportation for the day/evening.

For the amount of walking you'll likely be doing, your best bet is sticking comfortable shoes. It feels worth noting that I have seen several blogs warning against the tourist drenched horror of tennis shoes and sneakers, claiming that you'll stand out like a sore thumb. News flash, modern day big city dwelling Italians do in fact wear them on the regular. Take a chill pill, other bloggers.

On the other hand, don't go too casual - flip flops are a no. Aesthetics aside, they aren't fit for this amount of walking either, especially with crowds of people stomping around those vulnerable toes of yours (yes I realize it's a winter travel guide, but it needs to be said).

Let's Go to Rome!

My Personal Rome Packing List

When deciding what to wear in Rome, I concluded that chic and comfortable clothing would be, per usual, the way to go. My suitcase included:

  • A pair of sneakers (beige Converse Run Star Motions)

  • Two pairs of trousers

  • Two button up blouses

  • A long sleeve midi dress

  • Pajamas

  • Undergarments

  • Toiletries

  • Camera + Vintage camera bag

Finally, knowing that I may be visiting religious sites, I thought safe to toss in a more conservative outfit:

  • A black turtleneck

  • A full length black skirt

Day 1

Today's Look: Monochromatic red blouse, trousers, and belt. Beige converse platform sneakers. Vintage Pentax camera bag. Madonnina scarf tied in classic style around neck.

Sydney posing in front of a fountain, wearing one of her travel outfits, a monochromatic red shirt and pants with a vegan silk scarf around the neck.

Our first evening in Rome was spent weaving through the alleyways of Trevi District, a tourist saturated, but truly stunning area of the city. Our stroll took us to a neighborhood called Pigna, where we sat for hours over an bottle of inexpensive wine at pizzeria and restaurant Hostaria Pantheon, smack-dab right in front of the Pantheon (unreal), out of this world gelato from my favorite gelateria in the city, Gioliotti, and then back to Trevi District to end the evening with a photoshoot in front of the world famous Trevi Fountain.

Brenda holding bottle of red wine.

Brenda holding coats and smiling, standing in front of Rome Pantheon at night.

Best gelato in Rome, Giolitti, in green cup being held up by hand.
Don't be like me, don't get a disposable plastic spoon and plastic lined paper cup! I was tired and not thinking... cones are the way to go!

Sustainable fashion designer Sydney Duncan wearing monochromatic red outfit with white driving gloves, tencel scarf, and vintage camera bag, posing in front of Trevi Fountain at night.

Man taking photo stepping in front of Sydney.  they are wearing matching red outfits.

It wasn't until my return to the hostel, that I realized I had spent most of the evening with chocolate gelato on my face. Thanks Brenda.

Sydney with gelato on face.

Day 2

Today's Look: Monochromatic structured vintage coat, high neck blouse, and high waisted trousers. Vintage cream driving gloves. Beige converse platform sneakers. Vintage Pentax camera bag. Rodin's Inferno scarf tied old Hollywood style around head.

Sustainable fashion designer Sydney Duncan wears one of her Rome outfits, a monochromatic cream ensemble with a hand hemmed dragon print scarf tied around head.   She stands in front of a roman church.

When Brenda woke up feeling unwell, I realized that day 2 would be filled with solo adventures.

No stress, I love a little me time. I walked to the Monti District, one of Rome's most fashionable neighborhoods, and explored their beautiful arrangement of shops and cafes.

Rome's most fashionable neighborhood, Monti.

 It was here that I wandered into Little America, a relaxed street style clothing store that puts strong emphasis on keeping fashion slow and sustainable. I had a great chat with Jim, the gentleman manning the shop. We discussed the importance of being thoughtful in what we buy, the clean and cool aesthetic of Little America's brand image, and even a bit about photography.

Little America Monti Rome Storefront, with man posing in front of vespas.

From here, I walked until the colosseum was in view, and then turned along a statue lined road taking me up through the ancient ruins of Foro Romano. The weather was impossibly perfect, and of all of the paths I've taken since leaving the US 5 years ago, this was one of the most enchanting.

Stunning view in Rome of green statue holding scroll.

I eventually made my way to Via Del Governo Vecchio, a narrow street absolutely brimming with charm. Here I found two of my favorite vintage stores in the city: Ciao Luxury Vintage, the perfect stop for high end treasures, and Vestiti Usati Cinzia, a more eclectic and eccentric vintage shop.

inside of Rome vintage store Ciao vintage, which sells luxury brands.  On the wall hangs a green coat and portrait of a nude woman.
Ciao Luxury Vintage, Rome

For a full guide to Rome's best vintage clothing stores, check out the link below:

By nightfall, I had traveled miles upon miles on foot, and had explored nearly every vintage store the city had to offer. I returned to the hostel to meet a well rested Brenda, we grabbed dinner across the street, and then closed the night with gelato.

Sydney wearing monochromatic white outfit with purple dragon headscarf in front of orange tree and Rome church at night.

Brenda modeling super stylish scarf in the Rome streets.

Day 3

Today's Look: Monochromatic red knit midi dress and unbuttoned blouse. Beige converse platform sneakers. Vintage Pentax camera bag. Mauve North Face beanie. Rodin's Inferno scarf tied around waist.

Sydney in cool and trendy Rome neighborhood wearing street style outfit.

Our final day in Rome, Brenda and I woke up early and headed towards the one, the only, Vatican City.

What to Wear to Vatican city

Rooftop view from St Peters Basilica of Vatican City

In Vatican City, modest dress is essential to adhere to their strict dress code.

Appropriate clothing should cover bare legs (do not wear shorts) and shoulders and should include close toed shoes (do not wear flip flops). It is also respectful to remove hats and sunglasses when entering religious sites.

My visit to the Vatican, as it so turned out, fell on the morning of New Years Eve.

Initially I had laid out the all black ensemble, the one which I had packed especially for this occasion - a sleek turtleneck with a sophisticated full length skirt. A modest, church appropriate outfit. In the end, my heart couldn't bare to bring in the new year without color, and so I landed on a scheme of bold colors and print. It wasn't exactly the sort of look one would expect walking through St. Peter's Basilica - but I concluded that there is nothing in the dress code that says modesty means abandoning personal style (actually, in hindsight there might be, but the risk felt well calculated).

Sydney wears Modest clothing for Vatican City.

We lucked out beyond belief, because just as we reached the overhead view of the Basilica, Pope Francis himself stepped into view and began mass! This was in no way planned on our part, and it was a surreal way to bring in the new year, to say the least.

Birds Eye view of pop Francis giving mass inside of Rome's St Peter's Basilica

Close up of Pope Francis giving Mass


From The Vatican, we walked until reaching the winding cobblestone streets of Trastevere. This was without a doubt, one of the coolest neighborhoods in the city. It's trendy arrangement of shops, vintage stores, and cafes were, collectively, the cherry on top of my experience in this beautiful city.

Unlike the day prior, the weather of day 3 was not so ideal. We ducked and dodged to avoid the bouts of rain that would downpour every half our or so. Regardless, Trastevere was well worth the visit, and I'll absolutely be back on my next visit to Rome!

Brenda giving peace sign in front of entrance to Trastevere, one of the best neighborhoods to visit in Rome.

Tables, chairs, and umbrellas on the streets of Trastevere

vintage shoes and bags in Rome Italy's Twice Vintage Shop
Twice Vintage Shop, Rome Italy

As we made our way back to the hostel, we stumbled upon Groovin, a retail concept store mixing fashion, art and music - all to the tune of eco friendly trends and innovations. It's a high end shopping experience no doubt, featuring an impressive collection of boundary breaking fashions from a number of sustainable emerging designers. For the true fashion connoisseurs passing through Rome, Groovin is a must visit.

Rome's emerging fashion boutique, Groovin's storefront as viewed from outside.  There is a plush coat hanging in the window.

Ci vediamo dopo, Roma

When all was said and done, mine and Brenda's three days in Rome had played out like an absolute dream. This is one city that lives up to every bit of hype, and if you are reading this itinerary in preparation for your own Roman Holiday, I could not be more thrilled for you! Take my suggestions, and incorporate what feels right to you - but there is no need to over plan. Simply let the city guide you, and you'll be amazed by all of the incredible places that it takes you.

One last tip: Always keep in mind what an incredible honor it is to explore these stunning places, and do your best to travel conscientiously - shop second hand at stores and markets, minimize those single use plastics, walk instead of drive when it makes sense to, and take trains instead of planes when possible. It is this intentional mindset, that in my experience, has made the journey even that much sweeter!

Thank you so much for reading, and cheers to a sensational Roman Holiday of your own!


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