American Actor & Tommy Family Brand Ambassador Michael Rainey Jr. Takes Us Holiday Shopping at Tommy Hilfiger

SHARP & Tommy Hilfiger

This year, Power Book II star Michael Rainey Jr. is putting Tommy under the tree — Tommy Hilfiger, that is. An ambassador for the New York-founded fashion label, Rainey Jr. has a true Tommy Boy spirit: Inside the actor’s wardrobe, you’ll find a familiar balance between suave streetwear looks and enduring, heritage-inspired aesthetics. Like Tommy Hilfiger’s famously prep-school-ready silhouettes, Rainey Jr. is both elevated and effortlessly charming. Below, the Tommy family brand ambassador recalls his most memorable gifts from childhood and hands out a few tips on holiday styling.

What is the most memorable gift you’ve received during the holidays?

Back in 2007, I got two die-cast model cars — a Lamborghini Gallardo and a Murciélago. I was a kid obsessed with cars, so unwrapping those felt like receiving the real thing. I still remember how excited I was.

With so many parties and family gatherings, the holidays offer plenty of occasions to dress up. What are your favourite holiday looks?

Honestly, I’m a comfort-first guy during the holidays. Pyjamas or a cozy matching set — that’s my go-to holiday uniform when I’m relaxing with my family.

When you’re buying presents, do you shop for yourself, too?

No, not really. The holidays are when I focus on everyone else. I like making sure the people around me feel appreciated.

Tell us how you chose the gifts on this list. Did anyone specific — friends, family, etc. — inspire your choices?

I chose items I’d genuinely give to the people closest to me — things that feel personal, useful, and thoughtful. I think about what my friends and family actually enjoy and what fits their style or lifestyle.

What was your first encounter with Tommy Hilfiger? In the years since, how has your perception of the brand evolved?

My first Tommy piece was a classic polo tee. Over the years, I’ve watched the brand evolve with the times — embracing new influences, different cultures, and a more global point of view, while still staying true to that iconic Tommy style.

In your opinion, what makes Tommy products or pieces the perfect gifts?

You really can’t go wrong with Tommy. The pieces are timeless, easy to wear, and they work for everyone — whether you’re casual, preppy, or somewhere in the middle. It’s the type of gift that always lands.

Now, with New Year’s Eve just weeks away, we’ve reached the height of holiday shopping; luckily, at Tommy, it’s the ideal time to handpick this year’s hats, pants, and pyjamas. To celebrate the season of giving, Michael Rainey Jr. has come prepared with a curated guide to gift-giving. Taking us through the halls of Tommy Hilfiger, the actor shares which garments, gloves, and watches are on his family’s wish list. Find new favourites for the whole family below.