mens scarves
August 31, 2015

The Fall Guide to Mens Scarves

classic sir

Fall generally brings back loving memories of my childhood wardrobe. When the humid summer air turned brisk, and the wafting odor of rotting pumpkins on the neighbor’s doorstep lingered in the air, my bedroom closet would swell with rigid corduroys starched to perfection and a colorful bouquet of Cosby-esque sweaters for the coming school year. [...]

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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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photo courtesy of wikimedia commons
May 25, 2013

Iconic Watch Resurfaces After 50-Year Hiatus

Classic Sir

A watch sported by Sean Connery when playing James Bond in the 1965 movie, Thunderball, was recently found in dramatic fashion after being missing for many years. The geiger counter watch hadn’t been seen for decades and was thought to have been passed on by a cast member or employee of Pinewood Studios, where the [...]

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Classic Sir wardrobe essentials
May 23, 2013

7 Classic Essentials for Every Man’s Wardrobe

classic sir

Most men might not spend much time pondering the relative value of heel height, or the slimming effects of vertical stripes or block colors, but that’s not to say they don’t want to put the effort in. Happily though, the world of men’s fashion is full of timeless classics that help to take the guess [...]

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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
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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