Photo: Yimmy Yayo

If you’re looking for the most powerful hair dryer or handiest chef’s knife, those things can be easy enough to find. Other objects of desire are a little more taste-based. What’s the next status water bottle or hand wash, for instance? Regular readers of the Strategist will know that we’ve previously turned to resident Cool Guy Chris Black (he’s a partner at brand consultancy Public Announcement) to help us answer both of those questions, and to get more of Chris’s advice, he’s now answering reader questions for us in a regular column. If you have a burning question about the next fanny pack or Noah rugby shirt, drop us an email with the subject line “Ask Chris” at strategist@nymag.com.

Father’s Day is coming up! What are you going to get your dad? What are you getting your dad friends? What would you want if you were a dad?

My dad, Gary L. Black, is simple. He works, he runs, he reads. He is not a Luddite but did have an iPhone 4 until very recently. Over the years, I have had some gift-giving success with Hoka One One running shoes, Blundstone boots, and Levi’s 501’s. My misses include Apple AirPods (unused, still in the box) and a classic Burberry button-up that I have never seen him wear (he doesn’t listen to the Stone Roses). My takeaway: Don’t get too flashy. My tastes are not his!

Patagonia 7” Baggies Short $55 $55 I’m also thinking a pair of long (seven-inch) Patagonia Baggies in a fun color (he likes to show less leg than his son) feels like a good option. The Britpop masterclass will have to wait until Christmas. $55 at Urban Outfitters Buy

Carlyle Hotel From $595 My dad friends? They get my pity year round for the shit they have to deal with! But maybe an hour in the Chillspace sensory -deprivation tank would help them de-stress. If I were a dad (I truly GASP at the thought) — I would want a weekend stay at the Carlyle so I could be alone with my thoughts for 48 hours, spend a fortune on room service, and watch Bar Rescue reruns in peace. From $595 at Carlyle Hotel Buy

Your take on how the Stone Island pants are great to travel in got me thinking, what is the ideal Chris Black Travel Fit™️? Preferably for a long flight.

Ah, yes, the travel look, a much-debated topic in certain circles. When you enter a major airport in the USA, most people look like shit. They are wearing Shrek pajama bottoms with Crocs and a neck pillow. The other look that is most represented is the tired businessman in a Hugo Boss suit clutching a Tumi carry-on. I like to land somewhere in the middle.

When I sashay through the Delta terminal at JFK, I am aiming for respectable but still comfortable. My trusty black Stone Island pants, a simple white T-shirt with a vintage navy Champion hoodie, a seasonally appropriate jacket if needed, clean white socks, and crispy grey New Balance 990 v4. I am not a total slob in sleepwear, but I am also not a bleary-eyed consultant four Heinekens deep at the Uptown Brasserie loosening his Hermès tie while fighting with his wife on wireless Bose headphones. Honestly, just keep your toes covered and you already look better than half of the airport population.

What should I get someone who just graduated from Brown as a graduation gift? He’s a cool guy who’s a little bit of a snob.

Although I dropped out of high school, I have also been called a “cool guy who’s a little bit of a snob.” A nice pen is a great graduation gift.

Montblanc Meisterstück Platinum-Coated Classique Ballpoint Pen $440 $440 A Montblanc Meisterstück Platinum-Coated Classique ballpoint pen is my favorite; definitely get it personalized — it will last a lifetime and serve him well as he ventures into the depressing world of post–Ivy League adulthood. $440 at Montblanc Buy

Hermès Tarmac Passport Holder $225 $225 Maybe he is a taking a gap year — what could be more useful than a passport holder? This one from Hermès in a striking royal blue will keep his passport safe while he is doing some drunk soul searching in Thailand. $225 at Hermès Buy

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