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Five Starting Places for Building a Casual Wardrobe, Part One

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…

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Five Shoe Styles I've Found Useful -- and You May Too

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…

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What You Can Really Afford: Dickies Work Pants

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…

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Your Workhorse Casual Shirt, Chambray

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…

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Is Your Tshirt Cooler Than You?

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…

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The Most Practical Impractical Jacket: The Denim Jacket (part 2)

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…

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The Most Practical Impractical Jacket: The Denim Jacket (Part One)

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…

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Ten Great Sneakers for Spring

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…

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Feeling Pretty Psyched: The Style of Michael Stipe

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…

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Transitioning out of Dress Codes Altogether

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…

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Flyin’ the Flannel: A Comparison of Five Affordable Gray Flannel Trousers

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…

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Ugly Shoes That are Actually Kind of Great

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…

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Q & Answer: Can Undershirts Show?

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…

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Five Sneakers to Consider Right Now

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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How to Put Together a Successful Outfit

February 25, 2018

How To Put Together A Successful Outfit

Bruce Boyer, one of my favorite writers on men’s style, has a great intro to one of his chapters in Eminently…

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