Style Strategies
⇾ Michael Hill, Creative Director
of Drake’s
The creative director on the importance of small self-indulgences and sustainable shopping hacks
In the evenings, I’ll do a deep dive on the internet to discover new brands and pull different sources of inspiration on how to dress. One brand that I constantly hit the refresh button on is Drake's. Besides their pristine neckties, suits and footwear, the brand's editorial page is one of the best lifestyle journals from any clothing company. Whether the team is at the famed U.K. restaurant St. JOHN or shooting their latest seasonal campaign, the Drake's gang demonstrates that great clothes are an essential part of a life well lived. And the man bringing this all together is creative director Michael Hill.
Drake's was founded in 1977 by Michael's father, Charles Hill, and Michael Drake. The duo built the brand's foundation on bespoke ties and eye-catching scarves, which remain staples in the collection today. Growing up, young Michael tagged along with his dad on appointments and factory visits, so it was all but inevitable he'd take over at some point. He officially became creative director for the brand back in 2010, but his journey in gaining that position came from learning in his hometown and abroad, “I spent time in Italy learning the ropes and on Savile Row with Richard James—learning on the job is essential,” says Hill.
For a brand that's been around for over four decades, they're still relatively new in the States. Did you know Drake's has only been available in the U.S. for the past six years? One thing is for sure: They've helped set the tone for the Ivy/Prep resurgence with their made-in-England shirting and Casentino fleeces—not because it's a trend for them, but more of a principle of dressing well in timeless garments. The brand's look books mirror Michael's style with a sensibility of elegance and approachability. A guy wearing a soft-shouldered blazer, well-tailored trousers, and some well-shined Alden's looks both sharp and like he'd be easy to talk to. We caught up with him to see how he shops these days.
How has your taste evolved over the years?
It's constantly evolving, but I think it's about having an eye and an appreciation for things that are made well and have stood the test of time.
Wool flannel
tailored jacket,
$1,795 by Drake’s
What’s one item that every man needs in his closet?
You can never go wrong with a great navy blazer.
How would you describe your style in five words or less?
I'd say, 'off classic.' I'm going over the word count here, but something rooted in the last 100 years of men's clothing but made slightly different with my eye and approach.
Spots wool-silk
pocket square,
$115 by Drake’s
One item that you
cannot part with?
One of our classic squares. It's such a useful accessory. Keep it in your bag or pocket, wear it as a scarf, dress it up, dress it down, or tie it around a handle. I've always got one on me.
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Das Opera et Dust (2021),
price on request by Paul Housely
What’s something you’re looking to buy at the moment?
A small painting by the artist Paul Housely.
Three favorite brands, currently?
Rocky Mountain Featherbed, Anatomica and Mogi Folk Art, a beautiful textile, ceramics and art shop/brand started by my friend Terry Ellis in Japan.
Do you shop more online or in person?
Always in person when I can.
What city has the best shopping?
It has to be Tokyo. A weekend there and you can do the whole season. There's nowhere quite like it.
What’s a necessary extravagance
for you?
It might sound corny, but the real luxury is something small. Make yourself a cocktail in the evening, a bit of time to yourself, a routine. I don't do anything too extravagant, although I do like the Alden modified last too—but that's a shoe that will last a lifetime. Eating well but with simple ingredients is another luxury. Local and fresh, but not necessarily expensive.
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What is something you like to save money on or refuse to spend a lot for?
I wouldn't buy an upgrade for a flight; I wouldn't buy a really expensive car or a five-star hotel. If it costs a lot of money, you have to get a lot for it, and often you don't. I try my best not to waste money now.
Classic boxer shorts,
$65 by Sunspel
What’s something you in buy multiples?
Most things, actually! Drawings and paintings. White boxer shorts, chambray shirts and Drake's Games blazers.
Which do you experience more: buyer’s remorse or regret for not buying something?
I've gotten a lot better at buyer's remorse. I know what I like and rarely buy something and regret it. At this point, if I want something, I usually find a way—even if I have to sell something to get there. There's nothing I want or need—apart from that Paul Housley painting.
What’s one shopping hack that you can let everyone know about?
Bring your own bag.
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