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Ashley Graham · Feb 21, 2026

Eat the pasta, drink the wine, trade the pins

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Ashley Graham · Ashley Graham

There’s an energy when the whole world comes together in one city that you just can’t replicate. Being there reminded me that greatness takes time—whether it’s an athlete training for four years, a brand building for decades, or a bottle of Lambrusco years in the making.

The last time I was in Milan, I fell asleep during a content shoot. That’s Fashion Month for you—long days, quick changes, running on adrenaline. Going back for the Olympics felt like a completely different energy. No chaos. Just incredible food, global pride, and some of the fastest people I’ve ever seen in my life.

I was in Milan with my OMEGA family—you guys know I’ve been a partner of theirs for a bit, and seeing them in their element as the Official Timekeeper was really special. They’ve been doing this since 1932! I got to wear the Seamaster Diver 300M Milano Cortina 2026 edition, and the dial actually had this laser-engraved “frosting” that looks like ice. If you’re going to the Winter Olympics, you’ve got to nail the look.

You also have to commit to the vibe, and I couldn’t head to the heart of Italy without bringing my new baby along. As a newly self-minted Lucci Ambassador, I took one for the team and traveled with a custom wine suitcase full of Lambrusco. (When I say custom, I just mean that my business partner, Danny, put this personalized metal plate on it with “AG” and the Lucci logo.)

Traveling with a suitcase full of sparkling red was honestly my version of Olympic training. I originally planned to carry the Lucci case on with me, but after doing the research realized that wasn’t going to work. I always travel with a carry-on full of backup clothes (because you just never know), so I had to make a call: which bag was boarding with me and which one was getting checked?

Eight bottles went into the Lucci case. I padded them like precious cargo, zipped it up, and sent it down the belt. And when that suitcase came around at baggage claim, I have never stared at luggage so intensely in my life. No leaks. No ruby-red catastrophe. Not one bottle broke.

Gold medal energy.

There is something so surreal about pouring a glass of my own wine — born in the nearby Emilia-Romagna countryside — back in Milan, where it all began. I shared bottles with the OMEGA team, gifted a few to friends in town, and even popped one open during glam with my squad before an event. It felt really special to finally be able to talk about it openly and pour something I’ve been building quietly for so long.

When you work on something for years behind the scenes, there’s this shift that happens when it moves from private to public. From “my little project” to something you can place on a table, share, and sip. Watching people taste it, react to it, ask questions — that’s when it stops being an idea and starts feeling real.

⛸️ Queen Pin

Usually, I’m in Milan running between fittings and shows, squeezing in work during every spare second. This time, I actually got to slow down and immerse myself in the Olympics experience.

For instance, I fully got sucked into the pin trading tradition. Long story short: OMEGA gave us a set of pins to wear on our lanyards, and apparently trading them is its own Olympic sport. Different brands and companies design these beautiful little enamel pins, and you swap them with people throughout the Games. By the end, your lanyard is basically a scrapbook of tiny, colorful trinkets from around the world. I even found a security guard at the speed skating competition who was down to trade with me — there’s a video below. I was locked in.

And while I was there, I watched one of the wildest finishes I’ve ever seen — the Italian speed skater who literally crossed the line on his butt. The crowd lost it.

Speaking of speed skating, the athleticism was unreal. I consider myself an elite rollerblader (in my own mind), but watching those skaters move made me realize that if I want my butt to round out like that, I might need to get back on my blades. 😂

Truly though, I felt so lucky to be able to actually stop and watch these people who have worked their entire lives for one moment of impact.

It reminded me of the message I heard at church on Justin’s birthday recently: “What impact are you making in your world?” When we eventually go, the world keeps spinning. People move on. But the impact we leave endures.

These athletes are truly dedicated to their craft, and it was exciting to see them push their bodies, and themselves. Whatever your craft is—athletic or not—it’s so motivating to see how far we can take things when we really lock in. It makes me check my own “why” all over again. Does it match the impact I want to leave behind?

❄️ A Moment for the Dress

I looove winter fashion, so I was very happy piling on layers for the daytime events. OMEGA’s merch was thick, cozy, and honestly perfect for running around Milan in February. But one night was a whole different vibe.

OMEGA House is essentially OMEGA’s version of Soho House — a pop-up space in Milan where their ambassadors, clients, and friends of the brand can come hang, eat, lounge, and reset between events. It becomes this little home base during the Games. And every few nights, when an ambassador is in town, they host a party. This time, I got to host!

It was such a fun night — great music, amazing energy, and food from a Michelin-starred chef that we are still talking about. The dress code was “winter cocktail attire with a touch of frost,” so naturally… I had to crank up the drama.

I wore a GORGEOUS white hand-knitted dress from Zuleyha Kuru with a ponytail that hit my butt—the inches, honey! I felt like a figure skater on her way to snatch a gold medal. Huge thank you to my glam squad—Giannandrea Marongiu, and Maddalena Brando—for helping me pull off the ice queen vibe. Can’t wait to channel it again in the Alps 😉

🍝 Where to “Ciao Down” in Milan

Since I wasn’t running between shows, I actually got to visit some of my favorite spots (and try a few new ones). If you are in Milan, run, don’t walk:

  • Locanda alla Scala: We had an incredible lunch here. I highly recommend the Milanese risotto with veal sauce — it was phenomenal. I absolutely scarfed it down. For dessert, they brought out an affogato, and the ice cream is scooped from this massive, 1.5-foot mound of gelato that they scrape right in front of you 😭. I’ve been trying to cut back on caffeine, but that espresso was 1000% worth it.

  • Bice: It’s been family-owned since 1926 (so you know it’s real), and their homemade pasta is unbelievable.

    Al Baretto San Marco: This was such a vibe. We had rigatoni and wagyu that was out of this world. (We actually swapped eggplant pasta for the rigatoni at the last minute and it was the best choice of the trip.)

  • Ristorante Cracco: This is where the OMEGA House was, right inside the Galleria Vittorio Emanuele II. That place… I felt like I was in the Renaissance. I’d been there in September for a Marina Rinaldi dinner (we went the wrong way and I accidentally got a tour of the Galleria, which was spectacular). I was just as blown away this time around. We had an amazing meal that was SO clean and fresh. It honestly makes me a little sad about all the preservatives we have in food in the States—you can really taste the difference when the ingredients are this pure!

  • PIZ: For something more casual, this pizza spot is a must-visit. There are literally three things on the menu, so you can’t go wrong.

Ashley’s Final Thought Bubble 💭

There’s something about watching the Olympics that makes you zoom out. These athletes train for years — sometimes decades — for one moment. One race. One routine. One shot.

It reminded me that most things worth building take longer than we think they will. Whether that’s a body of work, a business, a family, a relationship, or your own confidence.

We’re all going for gold in our own ways. The timelines just look different.

If you were an Olympic athlete, what sport would you actually have a chance at?

I’m still claiming Rollerblading. 🛼

xo,

Ashley

A bible verse I love:
“Run in such a way as to get the prize.” — 1 Corinthians 9:24

My travel survival kit:
The OMEGA Seamaster (we love punctuality), my evolve together hydrating hand cream, original Beef stick from Anthem, Neuro gum, Revlon PhotoReady Rose Glow Face Mist, water, and a bottle of Lucci in the hotel minibar.

The Olympic sport I’m most obsessed with:
Short track speed skating

My Milan motto:
Eat the pasta, drink the wine, trade the pins.

Read the original on ashleygraham.substack.com

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