Ralph Lauren Plaid Shirt
October 8, 2014

Checkers & Balances – Guide to Plaid

Do's and Dont's

Being, as it is, past Labor Day, we are in prime plaid shirting season. Yet wearing this staple is trickier than you might think, fraught with unseen risks. Before you button down, read up. There are three kinds of plaid: vintage, mod plaid of the kind found on Don Draper’s casual jackets, which I lack [...]

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summer seersucker no tie
May 20, 2014

Summer Seersucker

How to Wear This Classic Cloth

With Memorial Day approaching, a whole host of sartorial chestnuts will soon be available to the fashion-conscious man until Labor Day, including summer seersucker. Here’s how to avoid looking like a wrong-side-of-history extra in Django Unchained.   Seersucker was first introduced to Americans via British India, the puckered fabric keeping the cloth away from the skin, facilitating [...]

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Dress Sweat Pants
April 7, 2014

Dress Pant Sweatpants: Workplace Etiquette

All Work No Play?

I spent a little over two years as a pretty strict raw vegan, another as a regular, not-insane vegan. Now I’m a lapsed vegan, but during that time, I’d eat very simple meals, made of whole foods. It was a great time for me, nutritionally; I always felt energetic, and was never sick. I ate a [...]

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how not to wear a tie
July 12, 2013

How To Not Wear a Tie

How To Stay Classic In the Heat, Part 2

If you read my article on cashmere, you’ll know I’m unafraid of statements that might make most Woosterians howl and fray their handlebar mustaches; here’s another: take off your tie. Take it off; gently drape it over a hook; whisper that everything will be okay; smooth its tired, wrinkled neck; and pop open your second button. Really, it’s a [...]

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Jay Gatsby Straw Hat Style
June 16, 2013

Jay Gatsby Upgrades Your Look

Classic Sir

  There was once a time in history when every man dressed to the nines all the time. When ladies were dolls and guys were dapper gentlemen. That lavish and extravagant era became commonly known as the Roaring 20′s. Heralded by one of this summer’s biggest blockbusters, The Great Gatsby, starring Leonardo Di Caprio, the [...]

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the art of shaving like a gentleman
June 3, 2013

How to Shave Like a Gentleman

The Art of the Shave

Only a true gentleman understands importance of a close shave. It’s no easy feat given that it gives lie to the idea that practice always makes perfect: you could shave day in and day out and still be left with results that simply don’t meet your standards. The truth is, a plain old razor and [...]

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stay stylish and warm during the summer months
May 11, 2013

How to Stay Classic in the Heat

Dressing for the Summer

I understand, I really do: you’ve forgotten what it feels like to be warm, it’s been cold for so long, and warm-weather-euphoria is bubbling through your bloodstream like champagne.  At this point in spring every Classic Sir looks forward to grilling and hitting the beach, but so often I’ve observed even the most level-headed sartorialist [...]

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Don Draper - Mad Men
April 14, 2013

Mad Men Yourself

Why Men Love Don: Part 2

I don’t claim to have as many problems as Don. Heck, I’m not even sure I’m as psychologically real. I do, though, know that there is something immensely comforting about wearing a uniform; you know who you are, because you know what you’re wearing, and vice versa. Oscar Wilde wrote in his essay 1891 essay [...]

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Don Draper
April 6, 2013

Mad Men Yourself

Why Men Love Don: Part 1

If you’re anything like me–and because you’re reading this I assume you are–you made a kindergarten-style paper chain to mark the days until the premiere of season six of Mad Men. Few cultural artifacts have made such an impact on contemporary public consciousness as this show has, and few creations have had as great an [...]

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8afcdd0404021770b77e04c7e7200d4a
March 19, 2013

The Basics of the Bow Tie Knot

Learn How to Tie a Bow Tie

Simply knowing when to wear a bow tie is just not enough. Knowing how to tie a bow tie separates you from the masses who don’t know the finer points of tying one, let alone the basics. If you are a first time buyer, remember that there are two variations of bow ties. The more [...]

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