Everyday Style
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May 24, 2018
Quiet Soles: Clarks And Crepe-soled Shoes
The current ugly footwear movement has roots in comfort footwear: shoes that marketed themselves as valuing orthopedic health over elegance,…
May 21, 2018
Five Starting Places For Building A Casual Wardrobe, Part One
It’s hard to talk about casualwear in the way you can talk about tailoring because you have to think about…
May 8, 2018
Five Shoe Styles I’ve Found Useful — And You May Too
Style is personal, very much connected to your lifestyle and personality. Which is why, even though we have some posts…
May 2, 2018
What You Can Really Afford: Dickies Work Pants
A significant influence on my personal style was a joke-y name tag sticker from an early 2000s magazine whose title…
April 30, 2018
Your Workhorse Casual Shirt, Chambray
Every once in a while, we’ll get an email from a reader asking if we have suggestions for how to…
April 27, 2018
Is Your Tshirt Cooler Than You?
Remember the “Jesus is my homeboy” tshirt? For a long time, when I thought of graphic tshirts, I thought of…
April 12, 2018
The Most Practical Impractical Jacket: The Denim Jacket (part 2)
Yesterday I talked a bit about the different styles of denim jacket that are out there, and what makes a…
April 12, 2018
The Most Practical Impractical Jacket: The Denim Jacket (Part One)
On balance, denim sort of sucks, especially for outerwear. It’s stiff when new and wears out reliably, ripping at stress…
April 5, 2018
Ten Great Sneakers For Spring
The weather is starting to heat up again in California, reminding me it’s almost time for camp collar shirts and…
April 4, 2018
Feeling Pretty Psyched: The Style Of Michael Stipe
Rock stars weren’t meant to stick around. They ignite, burn, and burn out. Rock music as a genre is reaching…
March 22, 2018
Transitioning Out Of Dress Codes Altogether
I’ve always paid attention to what I wear — I specifically remember the floral tie and pegged pants I wore…
March 15, 2018
Flyin’ The Flannel: A Comparison Of Five Affordable Gray Flannel Trousers
No one wants to be a flâneur anymore. It sounds too dandy, too affected. Even if the idea of strolling…
March 12, 2018
Ugly Shoes That Are Actually Kind Of Great
If you haven’t heard, ugliness is back in fashion. The sort of ill-fitting, cheaply made clothes that inspires your dad…
March 5, 2018
Q & Answer: Can Undershirts Show?
Jason writes to ask: Jesse recently said on his podcast that undershirts shouldn’t show. Is this a view shared by other PTO…
March 1, 2018
Five Sneakers To Consider Right Now
I just got back from a trip to Florida during which I wore sneakers almost exclusively (the versatile, relatively anonymous J….
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