The Story Behind My First Luxury Starter Bag

I hadn’t envisioned buying a luxury bag in 2023. After all, I was excited enough to be traveling to Europe for the first time in six years. However, as my dreamy trip to Italy got closer, I started to play around with the possibility. It would be a lovely gift-to-self after a few hard-earned years of work. And more specially, the purchase would be tied to beautiful travel memories. While I did not want to ‘force‘ the experience, I did my research a few months before to see if anything would catch my eye. And surely, I saw the YSL Cassandra. Purchasing this bag was not so straightforward. But I am so excited to finally share the story behind my first luxury starter bag.

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For my complete guide to buying your first luxury bag in Europe, read my post HERE.

The Research: How I Decided Which Bag I Wanted

There is much debate out there on which luxury bags are ‘truly’ worth it. But all debates aside, I think there is only one simple rule to follow: buy something you will genuinely love and cherish. When I started my research, I laid out a few key characteristics I loved in the bags I wear the most: structured, feminine, classic, fits everything I need…

After browsing a few designer websites, there was no bag that I felt truly captured these characteristics better than the YSL Cassandra. I adored that it could be worn as a top handle and crossbody, with my eyes set on the Beige. Additionally, I thought this style would be well-suited for work and everyday wear.

Buying my First Luxury Starter Bag in Italy

With a busy itinerary ahead of us, I made sure to carve time out for shopping. Luckily in Florence, we stayed at the Hotel de la Ville, which was conveniently situated between all the major luxury shops. I didn’t realize this part when I first booked it, but I am glad it worked out that way!

After a tiring afternoon of sightseeing, I decided to ‘take a break’ and pop into the YSL store that was just blocks away from the hotel. My intentions were to first see the bag, decide if I actually liked it, and maybe seal the deal in Milan when I had a few more days to sleep on it.

But once I stepped into the Florence store, things happened pretty quickly from there. The associate escorted me to the back where all the Cassandra bags were, and I tried on the mini size. I immediately noticed an issue…

The Mini Size was too Small!

The first hurdle I faced was that the Cassandra Mini was much smaller and flatter than I envisioned. Because the bag is sturdy and trapezoidal in shape, it fits less than it looks and there is not much wiggle room. Next, I tried their Medium size and I must have paced around the store several times before deciding it was the better option. I was not used to a bag of this size, even though from the pictures, it doesn’t look that big at all!

Popular colors sell out fast!

But one more curveball…The bag was all sold out in Beige at this location, as was the situation in Milan and Rome, where we would be at next. I learned from the associate that light neutrals (beiges, taupe) are very popular choices, which is something to keep in mind for the future.

There was an option of purchasing it in Florence, then having it shipped to Rome (our last city), so I could pick it up in-time before our return flight. The decision was not one I took lightly. While I didn’t regret my choices, it came with a few risks:

• YSL does not ship the bag until you purchase it. In other words, I didn’t have time to sleep on the decision. With the shipping times (2-4 days), it would arrive just around the time I get to Rome. And had I waited even a day, I may not have received it in time.
• I would buy a bag I’ve never seen in its actual color! This part would have felt safer with a shade like black or white. But with beige, I was a bit nervous: what if it was too dark, or too light? Or too yellow? My associate provided two YSL card cases to compare the color. The one I bought would be close to the top shade. I went off of this information, and took the leap.

• I would have to re-arrange the travel itinerary to pick-up a bag I may not like in the end. I was prepared for the fact that my feelings towards the bag might change once I saw it in full-form. In that case, I did not really have any other back-up styles I liked. And it also meant forfeiting some precious travel time to get back to Rome early for the pick-up.

I trusted my instincts.

Ultimately, I trusted my instincts and purchased my bag in Florence. I even returned to the store the next day to give all the other styles another look. At that point, I felt confident of my decision because there was no other bag I really felt drawn to.

Here are some other styles I tried, but I didn’t buy:

Left: YSL Solferino Medium Satchel (Taupe) | YSL Loulou (Greyish Brown)

Next stop: Milan. I, of course, stopped inside the YSL store inside the famous Galleria. But to my surprise, the store was much smaller! (I later learned there is another bigger store just walking distance from here.) As the associate shared with me in Florence, they did not have stock in the beige Cassandra.

Our time in Milan was a lot shorter. So overall, I was glad I made my decision earlier on without the added time pressure. That opened up time in Milan for some more relaxing activities, such as visiting QC Termemilano (well-known spa).

The Big Day: Picking Up My First Luxury Starter Bag

Two days before I arrived in Rome, my associate in Florence sent me a Whatsapp that the bag was delivered. The transit time was as promised (~3-days), and I was super grateful by how helpful she was even after my purchase. Once I entered the YSL store for the pick-up, the store associate brought out a giant brown box. From there, we took out the contents for a quick quality inspection.

A part of me wishes I could save the unboxing until I was home, peeling away the pristine layers of tissue paper for the first time. But with an international flight to catch the next day, I had to forego some luxuries. Luckily, the bag was stunning, and an even lovelier shade than I remembered. It came brand new, and because it was shipped from their HQ, the bag had never been touched on the sales floor!

Bringing my Beauty Home

The journey bringing back my first luxury starter bag was not a straight-forward one. But the final hurdle to cross was fitting everything for the ride back. I nested my YSL bag inside my trusty MZ Wallace Metro Tote (review HERE), which I carried onto the plane as my personal item. Then I stuffed my box and packaging inside my friend’s hardshell suitcase. We touched down in NYC, and everything arrived safe and sound 🙂 I couldn’t be more excited to wear this investment out soon.

Coming up soon: a review of this bag once I’ve given it a few months of wear, and what I learned when buying my first luxury starter bag. In the meantime, let me know if you have any tips for maintaining one!