Michael Tennant is the founder and CEO of Actually Curious, a pocket-sized party game that uses the science and psychology of emotional connection to create meaningful conversations quickly.

Which is exactly what we need right now. I saw a great tweet that said something to the effect of, “We’re not doing any more small talk in 2021. The next time I’m at a party talking to a stranger, I’m asking them what’s keeping them from achieving their life goals?”

What better way to achieve this goal than by skipping Cards Against Humanity at your next shindig for a game that prompts players to discuss whether higher education is a right or a privilege?

Only deep conversations in 2021!

We asked the Boston, Massachusetts-based founder to share about the personal style that carries him through his day.

Below, five (chilly-looking!) days of style from Actually Curious’ Michael Tennant:

Monday

Michael says: It’s spring in New England and I’m learning that the weather can swing from slightly cold to slightly warm. Today is on the cold side.

I’ve chosen to wear all black, with a few fun pieces for accent, and a bag for utility.

We’re going on a long walk exploring the city and I wanted a look that gave me confidence and swagger for those in the know, but also allowed me to blend into the understated culture that exists in Boston and is pretty natural to my demeanor.

OUTFIT DETAILS

• hat: Balenciaga
• jacket: COS
• hoodie: Transparent & Black
• pants: Dickies
• bag: Calpak
• shoes: Jordan Brand

Tuesday

Michael says: A mix of old and new. I tend to seek and wear pieces that are timeless and will bring me joy when I put it on, today, and possibly till they fall apart.

The vintage Mike Tyson and Evander Holyfield 1996 original match t-shirt reminds me of my days as a kid in Bed Stuy Brooklyn watching the major boxing matches on Pay-Per-View as a family, with “mad” people over from the neighborhood.

The denim jacket has been with me through thick and thin and carries with it many stories from my 20s and early 30s.

These Publish pants and Yeezy 500 sneakers are new uniform pieces to my joyfully curated collection of casual streetwear attire.

OUTFIT DETAILS

• Malcolm X hat: vintage
• jacket: Levi’s
• Mike Tyson t-shirt: vintage
• pants: Publish
• sneakers: Yeezy – Adidas

Wednesday

Michael says: When people ask me who my style icons are, I often say Bill Gates and Larry David.

I like being understated and comfortable and I think they pull this off with an ironic elegance. It also works because I don’t enjoy spending a lot on my clothes.

On the flip side of that, now that I have a bit more resources, I like to treat myself to shoes that bring me joy. I have these Yeezy 500s in Black and Stone. They are the perfect sneaker for my vintage subdued dad vibes aesthetic.

OUTFIT DETAILS

• hat: Target
• jacket: COS
• shirt: vintage
• pants: Dockers
• sneakers: Yeezy – Adidas

Thursday

Michael says: I recently moved to Boston and I’m learning that the New England Spring’s can keep you on your toes.

This look gave me the versatility to move into lighter color palettes while also being prepared for the short stretches on the cool and windy shaded sides of the streets.

The vintage Upper Deck hat adds the right kind of sports nostalgia for me, in this sports loving city.

The Nike Blazers, up to the boxy green Dickie cargo panta gives me a bit of hipster on the bottom to offset the normy sweatshirt and preppy vintage Banana Republic outer layer.

OUTFIT DETAILS

• Upper Deck hat: vintage
• jacket: Banana Republic (similar)
• pants: Dickies
• Vegas logo sweatshirt: vintage
• sneakers: Nike Blazer

Friday

Michael says: “A fun time-machine through commercial nostalgia. The 90s Fila Spaghettis are like the ones I begged my mom for as a kid.

The Harley T-Shirt with the American flag sleeves reminds me both of a world I can imagine having fun being a part of, as well as a world I feel so far removed from.

The Volkswagen hat is aspirational for the four door Golf “first-car” this native new yorker is holding out from owning.

Finally, the vintage vest that I wear because this shade of green makes me smile. I find it nice wearing my fears, dreams and memories right on my sleeves.

OUTFIT DETAILS

• hat: Volkswagen “Drivers Wanted”
• vest: vintage
• long-sleeve shirt: Harley Davidson
• pants: Dickies
• sneakers: Fila – 90s Spaghetti

Check out Actually Curious’s newest edition focused on human rights!

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Want more real guy style? Discover what this SF-based stay at home dad wears in a week.