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Gifts for Modern Mad Men

By Jonathan Sposato

Jonathan Sposato is the chairman and co-founder of Geekwire, as well as a prolific startup investor and former CEO of photo editing and design service, PicMonkey. He’s also an outspoken champion of gender equality, having penned Better Together: 8 Ways Working with Women Leads to Extraordinary Products and Profit, and an advocate against homelessness as co-chair of United Way King County. And he does it all while being a supremely snappy dresser with a keen eye for design and style. Jonathan is a bit of a modern mad man, and here he shares his best kept secrets for gifts that are sure to impress the stylish guy on your list this year.

Gifts for Modern Mad Men
Tuesday December 15th

Jonathan Sposato is the chairman and co-founder of Geekwire, as well as a prolific startup investor and former CEO of photo editing and design service, PicMonkey. He’s also an outspoken champion of gender equality, having penned Better Together: 8 Ways Working with Women Leads to Extraordinary Products and Profit, and an advocate against homelessness as co-chair of United Way King County. And he does it all while being a supremely snappy dresser with a keen eye for design and style. Jonathan is a bit of a modern mad man, and here he shares his best kept secrets for gifts that are sure to impress the stylish guy on your list this year.

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Q Timex Reissue 38mm Stainless Steel Bracelet Watch

$179
Jonathan Sposato

“If you know something about watches you'll know this classic 'Pepsi' bezel is an homage to one of the most famous watches in the world, the venerable Rolex GMT. But even if you can't care less about watches, this new Timex reboot is simply a great durable timepiece for $175 bucks. If you wear it, you signal to the world that you know what you're doing, have great taste, and are smart with your money. The vintage nods in the design warm my heart, and at 38mm width it will look good on everyone.”

Jonathan Sposato
Q Timex Reissue 38mm Stainless Steel Bracelet Watch

Biker Jacket from Lewis Leathers

$1,015
Jonathan Sposato

“The best leather biker jackets ever made. These hearty, classic, and always stylish jackets are about as original as you can get, next to their American equivalent, the famed Schott Perfecto. Rumor has it that seminal punk band the Ramones ditched their Schott Perfecto's in favor of Lewis Leathers. And because these are British, you can even get them tailor fitted to you. I am embarrassed to admit I have three of them—two vintage and one new. Try the horsehide over cow for a stiffer 'slicker' look. One of my vintage ones dates back to the late 50's and it looks amazing.”

Jonathan Sposato
Lewis Leathers
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Sweater from Elder Statesman

$1,795
Jonathan Sposato

“Words cannot describe the unbelievable softness and craftsmanship of a handmade Elder Statesman sweater. I would venture to say that these are bar none the most beautifully made sweaters for either men or women in all of existence. This is a small volume boutique weaver that started out making gorgeous blankets originally, and recently transitioned to sweaters. Minimalist in shape and complexity, but oh so incredibly rich in detail and color. If I was only allowed one versatile piece of outer wear on a weekend trip, this would be the only thing I need. You have to feel these to believe.”

Jonathan Sposato
Elder Statesman Smoking Jacket (Cashmere)
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Vintage Korean War Era M65 Field Jacket

$100
Jonathan Sposato

“I don't know what it is about a classic M65, but I've yet to meet a man who doesn't look handsome in one. Doesn't matter if you're too tall or too short, fat, or the hunchback of Notre Dame, a properly fitted M65 will always look leading-man. And if you’re inclined to pick one up, go for a vintage one from Korean war era to Vietnam period (prices range from $19 to $500 dollars depending on patches and condition) because they were the most hearty and look like they served their country with distinction and lived to tell about it. My own father's M65 from Vietnam is long gone, but I managed to pick up a couple at vintage clothing stores years ago and they are truly among the most special pieces in my own wardrobe. You can wear them working out in the yard and use the myriad of pockets to store gloves, keys, tools, etc. You can go punk like Travis Bickle or hipster like kids in Harajuku.”

Jonathan Sposato
Vintage Korean War M65 Field Jacket

The Boiler Suit

$58
Jonathan Sposato

“Commonly referred to as overalls or 'onesies,' the boiler suit was actually put into heavy rotation by none other than Sir Winston Churchill himself. Legend has it that he walked into his Savile Row tailor asking that they make him something he can jump in and out of in emergency situations. He also wanted to look 'smart' navigating the rubbled streets of war torn London, protected from mud and rain. Thus was born the onesie as a suit alternative. Personally, I think the good old navy blue ones from Army Navy Surplus are best, as they are always available in military colors favored by pilots. This one from Australian luxury denim brand One Teaspoon is also pretty cool because of its relaxed cut. Notice the drop crotch and inseam length to peg and roll them for a great look.”

Jonathan Sposato
One Teaspoon Khaki Utility Suit
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This Guide Supports

United Way of King County

720 2nd Ave, Seattle, WA 98104
Jonathan Sposato

Fresh Chalk has partnered with Jonathan to support the United Way of King County. “The United Way of King County helps more people in our region than literally any other philanthropic agency combined,” says Jonathan. “They impact the lives of hundreds of thousands of people throughout King County through rental assistance, housing the homeless, and keeping families financially stable. What's more, $0.95 of every dollar you give goes directly to someone in need. You simply can't get a better ROI on your good money anywhere else.”

Jonathan Sposato