In this blog post, I’m sharing the story of an undercover shopping mission along Chicago’s Gold Coast, a day of undercover shopping in Chicago focused on Chicago Gold Coast shopping and luxury handbag shopping. What follows is my personal experience, in the exact order I visited each location: Hermès at 25 East Oak Street, Prada at 30 East Oak Street, Fendi inside Neiman Marcus at 737 N. Michigan Avenue, and finally Gucci at 900 N. Michigan.
Hermès — 25 East Oak Street
My walk began at Hermès on East Oak Street, where the moment I stepped inside I felt as though I had entered a quiet, sunlit gallery. The interior was exceptionally clean and well maintained. The marble floors were immaculate, shining without a single scuff in sight, and the glass display cases looked like jewel boxes, each one carefully curated and spotless. A staircase rose to another level, adding to the sense that there was always something more to discover just out of view.
The employees were professionally dressed and carried themselves with an effortless calm. No one hovered, but I never felt ignored. When I began to browse the handbags, a sales associate approached with a warm, unhurried greeting and asked how she could help. Her manner was welcoming without being pushy, and she seemed genuinely interested in what I liked rather than what she wanted to sell.
When I mentioned I was looking for a crossbody bag, she immediately suggested the Hermès Evelyne Mini. She presented it with care, pointing out the perforated Hermès logo on the front and the long strap that allows the bag to sit comfortably crossbody. The leather felt supple and luxurious beneath my fingers, and the size was perfect for daily essentials without ever feeling bulky.
As we talked, it was clear she knew the product line inside and out. She answered my questions about leather types, wear over time, and how to care for the bag in a straightforward, knowledgeable way. There was no scripted sales pitch, just calm expertise and an easy confidence that made me trust her recommendations.
Although I didn’t make a purchase that day, the entire experience felt considered and effortless from beginning to end. When I asked about pricing and availability, the associate walked me through my options with patience and clarity, making sure I had all the information I needed to think it over without any pressure. The Evelyne Mini was carefully returned to its display, and I never felt rushed or dismissed for choosing to wait.
From cleanliness to product quality to customer service, Hermès delivered on every point of my undercover evaluation. I left feeling genuinely welcomed and well taken care of, still thinking about the Evelyne Mini but deciding to give myself time before making a purchase, and I would happily recommend this location to anyone considering a visit.
Prada — 30 East Oak Street
From Hermès, it was only a short walk down East Oak Street to Prada. Even before stepping inside, the store made a statement. The display windows were immaculate, featuring mannequins styled like they had just stepped off the runway, each look precisely put together and free of any distracting clutter or fingerprints on the glass.
Inside, Prada’s distinctive aesthetic took over. The walls were a fresh, unmistakable green, and the black-and-white checkerboard flooring gave the space a crisp, graphic energy. It was bright, orderly, and polished—every surface and fixture felt intentional and well cared for. Beautiful dresses hung in careful arrangements, adding to the sense that this was a place where fashion and presentation are taken seriously.
The employees were all well dressed in black, moving through the store with a quiet professionalism. I was greeted promptly, and when I made my way toward the handbags, a sales associate stepped in with the right balance of attentiveness and space. She asked thoughtful questions about what I was looking for and then introduced me to a bag that immediately caught my attention: the Prada Carry Mini.
She walked me through its details with clear product knowledge. The Carry Mini featured detachable leather handles and a removable key ring, which added both function and a subtle touch of personality. The front pocket gave it a practical edge, while the magnetic closure kept the silhouette clean and streamlined. What struck me most was the leather itself—very soft to the touch, with that refined pliability that suggests it would age beautifully.
I took my time examining the bag and imagining how it would fit into my wardrobe. The associate never rushed me or tried to push the sale. Instead, she offered information when I asked, then stepped back to let me decide. Ultimately, I chose to think about the purchase rather than buy it on the spot, especially after my investment at Hermès. She responded graciously, handed me her business card, and invited me to return anytime if I had more questions.
Between the polished environment, thoughtful design, and high level of professionalism, I left Prada feeling welcomed and respected as a client, even without a shopping bag in hand. I would absolutely recommend this store for its customer service, distinctive aesthetic, and well-crafted pieces.
Fendi Inside Neiman Marcus — 737 N. Michigan Avenue
From Oak Street, I made my way toward Michigan Avenue and stepped into Neiman Marcus at 737 N. Michigan. The overall store was immaculate and well organized, with wide, clear walkways and thoughtfully arranged displays. It had the feeling of a carefully edited department store where each brand still retains its own identity within the larger space.
The Fendi area occupied its own dedicated section, immediately signaling a shift in mood. The focus here was on leather goods for women, with bags arranged in a way that made browsing easy, not overwhelming. Everything appeared clean, orderly, and considered—no clutter, no disarray, just a calm presentation of Fendi’s designs.
A sales associate greeted me promptly and asked what I was interested in. When I told her I was exploring handbags, she led me straight to one of Fendi’s icons: the Peekaboo. The bag was secured on a wire for security, but that didn’t detract from its appeal. She carefully brought it closer and began to explain the features with clear familiarity.
The Peekaboo she showed me had a soft calfskin exterior that felt luxurious but structured, with tone-on-tone lining that kept the overall look subtle and refined. Inside, two separate compartments were divided by a central partition, making it easy to imagine how a day’s worth of essentials could be neatly organized. The twist-lock closure added a satisfying, tactile moment to opening and closing the bag, and the gold-tone hardware complemented the design without overpowering it. The interior was lined with lambskin, which gave the inside an unexpectedly plush, almost secret softness.
I was genuinely tempted. The Peekaboo has a quiet confidence about it—classic, but never boring. However, with my new Hermès Evelyne Mini already on my mind (and my credit card statement), I decided not to purchase another bag that day. The associate responded with understanding, handed me her business card, and thanked me for stopping by.
Between Neiman Marcus’s overall organization and the dedicated Fendi section’s thoughtful presentation and product quality, the experience felt polished from start to finish. I left feeling welcomed, not pressured, and impressed by both the handbag design and the associate’s knowledge.
Gucci — 900 N. Michigan
My final stop was Gucci at 900 N. Michigan. Even from a distance, the building’s facade caught my eye—striking and elegant, setting a glamorous tone before I even reached the doors. In the windows, handbags were displayed like art pieces, each one given enough space to stand out.
Inside, the store was clean, bright, and immediately welcoming. The layout felt open, and the overall atmosphere was polished but not intimidating. A sales associate approached with a friendly greeting and asked what brought me in. When I mentioned I was exploring shoulder bags, he led me to an all-black Gucci shoulder bag that instantly stood out.
The bag was large enough to be practical without feeling oversized, crafted from goatskin that caught the light in a subtle, refined way. It featured palladium-toned Double G hardware on the front, a detail that gave it a recognizable Gucci signature without being overly flashy. The interior was lined with black cotton, keeping the inside durable and easy to care for while maintaining a sleek, monochromatic look.
When I tried it on, the bag seemed to shine like a gem against my outfit—understated, yet undeniably special. The associate answered my questions thoughtfully and never rushed me, allowing me to step in front of a mirror and really consider how it fit my style and my needs.
As much as I admired it, I ultimately decided to think about the purchase rather than commit right away. The associate responded graciously, handed me his business card, and encouraged me to return if I decided the bag was right for me. His attentiveness and product knowledge left a strong positive impression, even without a sale.
Based on this visit, I would recommend Gucci at 900 N. Michigan for anyone seeking attentive, informed service in a clean and beautifully presented environment.
Reflections on a Day of Undercover Luxury
By the end of my walk, I had not only a new Hermès Evelyne Mini on my shoulder, but also a clear sense of how each store measured up in terms of cleanliness, product quality, product knowledge, and customer service.
Hermès stood out for its pristine, gallery-like atmosphere and exceptionally knowledgeable, welcoming associate who guided me to a purchase I truly love. Prada impressed me with its runway-worthy window displays, striking green walls, and employees who balanced professionalism with warmth, even when I chose not to buy. Fendi, within the polished setting of Neiman Marcus, offered beautifully designed leather goods and a tempting Peekaboo presented by an associate who knew every thoughtful detail. Gucci closed the day with an elegant facade, an all-black goatskin shoulder bag that felt like a hidden treasure, and staff whose attentiveness made it easy to imagine returning.
Each stop along this undercover assignment delivered its own version of luxury. Together, they turned a day of evaluation into something more personal: a reminder that the best shopping experiences aren’t just about the bags themselves, but about how you feel while discovering them—seen, welcomed, and never rushed.
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