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Keegan-Michael Key Talks Style and Watches
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Keegan-Michael Key Talks Style and Watches
Stitch Fix

Keegan-Michael Key Talks Style and Watches

Keegan-Michael Key on His Personal Style and Holding Onto What Matters Most

Keegan-Michael Key is a busy guy.

The multidisciplinary actor and comedian recently announced the Detroit Lions’ second round draft pick at the NFL draft. He’s reportedly involved in several projects, including a reunion with Jordan Peele for a new Netflix film and was bestowed as “a national treasure” by Mike Myers at a recent talk hosted by the streaming service.

On top of all of that, he also announced a partnership with personalized styling service Stitch Fix as part of a larger effort to help guys update their wardrobe. Key says that prior to partnering with Stitch Fix, his wife (film producer, director and actress) Elle helped him craft his daily style, which he says leans towards comfort and “basic, clean lines”.

As we caught up with Key by phone, it became clear that he shares more of a pragmatic relationship with clothing and style. While he collects a few particular things, it’s more about having reliable looks that get him out the door and complement those specific items he wants to highlight.

The following interview was edited for brevity and clarity.

AskMen: How do you define your personal style?

Keegan-Michael Key: I’d say it’s comfort first, followed by clean, basic, easy and soft lines. I'm a person who enjoys things that are simple and timeless. I like to be stylish in an understated way. Professionally, I think (actor) Ryan Reynolds is a master at red carpet style. He’ll often wear a three-piece suit with no tie, and he’ll add something a little extra that has a nice classic feel. I like classic with a bit of new, like dressing up a suit with a simple accoutrement, like a pocket watch or a watch with matching cufflinks. I like any kind of pop, maybe a pocket square every now and again. If it’s a suit compared to a tuxedo, I may turn to a sock to complement another piece. I’m the one who wears a shoe that’s one solid color, and has 2-3 different colors to choose from.

You mentioned watches a couple of times. Do you turn to a specific brand or style?

I’m more of a wristwatch guy, but if I’m wearing a tux, I won’t wear a watch. I remember someone telling me that ‘when one is wearing evening wear, there’s no need to wear a watch as you’re going out for the whole evening’. Essentially meaning that you’ll be out all night, so you don’t need to know the time. However, I do have one watch that I might wear with a black leather strap, and with suits I like to wear an alligator strap. I have a good number of watches.

So would you say you’re a watch collector?

I’d say I’m a wristwatch enthusiast and a collector. I have a large collection of Shinola watches as I’m from Detroit and it’s a great way to represent my hometown. That's probably the brand that I’m most loyal to – I connect to their watches from a point of nostalgia and emotionality. I also own a couple of Rolexes and a Patek Phillipe, and I like other kinds of watches, too. I’m that guy who goes on sites and looks at apps and thinks about which watches I like. I’ll buy a watch to commemorate an occasion like a graduation, winning an award, career milestone or an anniversary.

Is there anything in particular that inspires your personal style?

I have always resonated with the Rat Pack era in Vegas. There’s something about the Rat Pack and that nice, clean classic 1960s look, even though I wear clothes with a sprouty square. You see a black and white photo of Frank Sinatra in Palm Springs on a casual day: he’s wearing a casual polo and really nice slacks and you think, ‘he clearly looks comfortable and at ease, but he also seems to be stylish.’ He’s not just on stage doing revue and looking sharp. That era influences me now, even with denim, especially how clean, classic and comfortable that look is.

In the midst of my recent life, I would sometimes get overwhelmed, and I’m fortunate that Elle has a very good sense of style, so she helps me decide (what to wear). Now, I have her and Stitch Fix to help me find items that match.

In some of the materials around the partnership launch, you mentioned that you were hoping to help men finally let go of clothing they no longer need. Are there any other categories where you think this could apply?

That’s a good question. I wouldn’t call myself a huge collector of things. I do collect graphic tees representing different points of my life. I think that a t-shirt can be like a bumper sticker, showing sentimentality or overriding that with other values. However, I can also jettison some of these from my experience — it’s time to let go because where I am on my journey now. I think about it as, ‘Does it belong in the storage space in the basement or is there another human that would enjoy this demarcation of a moment in time?’

Especially in this digital age, you can purchase anything in the blink of an eye. That’s an interesting thing — that doesn't mean one should possess it, but I think for me personally I can figure out what matters most.

Is there anything that falls under that description — that matters to you?

I have a Lions lapel button that used to have a magnet, but it doesn’t have it anymore. This one pin is really important (to me). Lions president Rod Wood gave me that button and I’ve had it for about 5-6 years. It's something that reminds me of where I’m from, reminds me of my relationship with my wife and our shared love of sports and her support of me. She’s done so much to help me have this more intimate connection with the team. (Ed note: at this point, we asked Keegan-Michael if he had a photo of this pin, and he didn’t, so he paused the interview to stop and take a photo of it, which you can see below).

It’s just this tactile thing, but there’s something also classic about it. It brings me a certain amount of enjoyment. When I got the pin, we got to watch the game that day from the box and I’ve been friendly with the president ever since. To have an experience with an object or a piece of clothing … hundreds of endorphins pop when you have that physical feeling.

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