The Tailor Game feat. Rich Freshman

September 2nd, 2014

Meet my new friend Rich Freshman, West Hollywood tailor and clothier. Growing up in Memphis, he learned the value of dressing like a gentleman early in life.

“I taught myself to sew at 13 because of a crush I had on this girl. I was a kind of geeky kid, and i didn’t dress very well. From my middle-school observations I figured the easiest way to get her attention, and the attention of other pretty girls, was to: 1) become an athlete, 2) become an asshole, or 3) learn how to dress better than my competition. Athletics weren’t my thing, and I was a really nice shy kid, so being a jerk to women was out. I chose fashion and although things never worked out with my crush, I fell in love with menswear and tailoring.

That summer I was definitely my school’s ‘most improved’ in the fashion department. I went from knowing zero about fashion at 13 to being a student of Ralph Lauren and Brooks Brothers. I never wanted to be like Mike – I wanted to be like Ralph. I wanted to study architecture growing up, but fashion became my breakfast, lunch, and dinner. I found power and gained confidence from it. In a way this is my architecture. I design menswear, take measurements, draft patterns, create finished structures, and modify them as needed.”

Two things you need to know about Rich. 1) He often wears a (color coordinated) measuring tape as an accessory with his sharply tailored outfits. It’s a genius marketing play that has brought him some significant business. 2) He makes suits, but rarely wears them. He prefers the added creativity of separates.

Here he shares his story and shows us the art of the double-breasted blazer.

1. Colorful Cord

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“I don’t recall wanting to be a kid, really. I’ve always wanted to be an adult and to be treated as such. My dad was a pharmaceutical rep in the 90s… He was pretty fly and I observed how well people treated him, and how much they respected him. I wanted that identity.

I skipped over the baggy jeans and Jordans and went straight to polos, drivers, chinos, cable knits, etc. I was a broke kid, but I would save up and find good sales at Brooks Brothers… It would trip the sales staff out, I think, because here’s a 15 year-old black teen shopping with middle-aged white executive types. I can still recall the level of respect they showed me once they saw how serious I was. That’s what made me want to do this even more.”

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“I’ve always enjoyed color and pattern-mixing. I don’t do the over-the- top bedazzled stuff, but I’lll take a teal jacket, mix it with a muted-brown glen plaid trouser, and balance it off with a cognac shoe.”

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  • Blue corduroy jacket by Rich Freshman ·
  • Blue striped shirt by Rich Freshman ·
  • Yellow knit tie by Rich Freshman ·
  • Sunglasses by Ray-Ban ·
  • Brown loafers by Ferragamo ·
  • Red briefcase by Samsonite (Vintage)

2. Fresh Fall Salmon

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“After a year of studying architecture in Memphis, I dropped out to start my first tailoring business. It was an alteration outsourcing company. I would drive all over the city picking-up alterations from local dry cleaners, take them back to my loft, do the tailoring, and then take them to back to the cleaners. Eventually, the business grew, and the following year I opened a tailoring storefront in downtown Memphis.

I spent my off days hanging out with and assisting other tailors, trying to hone my craft. I’m a big believer in modeling. If you find someone with skillsets or traits that you admire, spend some time learning from them…  My buddy from high school introduced me to the tailor who would ultimately become my mentor; Michael C Thomas.

He was in his 30s when i was in my 20s, you know. He was young, he was cool, and he had impeccable style. His shop became a regular spot and he’s served as a mentor ever since.”

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“When my brother, my daughter, and I moved out to San Diego in 2010, I saw a void in mens’ style – especially tailoredwear. I recognized an opportunity to create what i felt was missing. So I developed my own aesthetic and shifted from alterations to made-to-measure. This was the natural course of my evolution as a tailor, I think.

Now I’m here in LA trying to make my mark in the industry and, like Dan, trying to show the world that tailoring is cool again baby! And this is what it looks like for us.”

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As a traveling tailor, Rich scores some points in my book for keeping his fabric swatches and measuring tools in vintage suitcases. More on that later…

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  • Salmon jacket by Rich Freshman ·
  • Grey dot shirt by Rich Freshman ·
  • Burgundy dot tie by Halston ·
  • Brown briefcase by Samsonite (Vintage) ·
  • Brown loafers by Ferragamo

3. Windowpane Jacketing

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“My clients in LA vary. I have male clients and female clients. From young talent managers to established Grammy winners. The common denominator is that they all wanted to improve their image at some point. Even the clients who initially weren’t very style conscious have become impeccably dressed men and women… It makes me proud.

My typical aesthetic is very clean, british, and inspired by 40s Americana. Think Vegas, Sinatra, Palm Springs. It’s clean and sexy, but it pops.”

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“Regarding what to look for in a clothier, treat it the same as if you were looking for a personal trainer. If my goal is to get jacked, i’m not going to look for the slim yoga trainer. I’m going for the biggest trainer available. I want the guy who is better than me and has the results I’m looking to achieve.

If you want a very conservative corporate style, find a conservative tailor/clothier. If you want to hit the red carpet circuit and grab attention, find a tailor who specializes in that. Ultimately it’s a relationship business and you want to make sure that your interests are aligned.”

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Windowpane jacket, trousers, shirt, pocket square and duffle bag by Rich Freshman. Glasses by Hickey Freeman. Monkstrap loafers by Zara Man. 

  • Brown windowpane jacket by Rich Freshman ·
  • Glasses by Hickey Freeman ·
  • Brown knit tie by Rich Freshman ·
  • Brown monkstrap loafers by Zara
  • · Grey trousers by Rich Freshman


Essential Light Gray Trouser

Thanks, as always, for reading and special thanks to Rich for participating!

Yours in style,

Dan Trepanier

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