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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preview_harris-tweed-loop-scarf
March 4, 2013

On Cashmere

Too Soft?

Maybe it’s just me, maybe it’s my penchant for all things preppy, maybe it’s that fleece (the least preppy fabric) or anything resembling fleece gives me the howling fantods, but I have to finally come out and say it: I don’t like cashmere. I kind of hate it, actually. Put down your pitchfork. You, pocket [...]

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Corduroy-1
November 27, 2012

Corduroy Day

The Best Day Of The Year

Last Sunday, November 11 was, other than St. Crispin’s Day and Festivus, my favorite holiday. The wales align on Corduroy Day, the date that most resembles the “cloth of kings” (corduroy’s French translation). So, in homage, I’d like to spend a meditative moment or two in tribute to this classic autumnal fabric. No other fabric [...]

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MarcoFosterBanner_2
September 20, 2012

Mr. Marco A. Foster

September 2012

Classic Sir is proud to present September’s Gentleman of the Month, Mr. Marco Foster. He took some time to talk with us about Chicago Models, Fashion’s Night Out, and One Hope United. CS: You’ve been spotted at events all over Chicago. How do you stay socially active and keep in touch with what’s happening around [...]

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Jason Sebacher sporting a bow tie.
September 18, 2012

How, Where, and Why to Wear a Bow Tie

Ready to Wear

Bow ties have that unique quality of looking either completely fabulous or entirely dreadful without any middle ground.  And we’ve all seen them, haven’t we?  At a club or bar, or traipsing around downtown, there they are–rarities, like glints of gold glittering through an ash heap: a man sporting (and what other verb is there?) [...]

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Oscar Wilde
July 24, 2012

What to Wear to the Theatre

A Playwright's Perspective

Bertolt Brecht, the very, very German playwright who penned such works as Mother Courage and Ambien: The Musical, correctly wanted his audiences to attend the theater coming from the local pub.  In other words, he wanted the everyman, the fishmonger, the lowly tobacconist to go see plays.   Yet anyone who regularly attends the theatre [...]

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James Dean
May 9, 2012

James Dean Reloaded

Ready to Wear: Michael Bastian

“For his return, Bastian presented an homage to James Dean, whose squinting, moody visage, picked out in the designer’s logo, was splashed over the backdrop. The first model emerged, a fifties kid in dungarees, penny loafers (with pennies; Bastian is nothing if not detail-oriented), and windbreaker—the rebel without a cause of Roy Schatt’s famous photo. [...]

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