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


    “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.”



    “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.”



    • 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


    “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.”



    “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.”


    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…



    • 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


    “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.”


    “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.”




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

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

    Yours in style,

    Dan Trepanier

    Shop Custom Menswear Made in America


    Take me to the Shop

    • CJ

      Great tailoring, especially the salmon blazer! Even more amazing story!

    • I nearly stopped reading

      Why do men think you have to be a jerk to get a woman’s attention? Please kill that myth in man world and stop making so many assumptions.

    • Alex

      Nice feature! One question: What’s with the pocket placement on that last DB sport coat? Looks like the pockets are inside of the button area and even covered on one side when the jacket is closed…

    • AdamE

      Awesome looks, I wanted to hate the pink blazer, electric blue pants combo, but it’s legit! I’ve always been a bit nervous about going with a suit in a really bold shade, but if you split them up as separates, it makes them more palatable and approachable, definite inspiration to try something a bit louder.

      I personally love the tailor’s tape as an accessory for a conversation starter. If you weren’t a tailor, I could see it as being off, but as a custom tailor, it’s a great signature, and I’m sure when paired with killer looks the 3 here could get you some business… Better than handing out business cards for sure!

    • Jen

      Incredible tailoring and such dapper style. Been a fan for a while now. Great shots, congrats!

    • Stuart

      Throwing seven different kinds of smoke. All the looks are fresh, thoughtful and brilliantly tailored.

      The advice on finding a tailor that matches your style is also spot on. As is the pseudo psycho-analysis of American middle school. Glad you opted for number three.

      • Rich Freshman

        Stuart, so am I. Can’t imagine how different my life would be if I had opted for 1 or 2. Thanks for the support chief.

        Follow me on IG.

        • Guccio1971

          Always so fresh, bro…..big ups!

    • Gazman

      Some daring pattern matching. But what’s with the measuring tape?

      • Rich Freshman

        I’m a tailor baby. Gotta represent my craft

        • Gazman

          Yes, and better to have it in every photo just to underline the point.

    • Zach_Trebalt

      Great Article Dan. Rich’s style is impeccable. My favorite was the 1st look with the corduroy jacket. You sir are one badass designer and the future of tailoring!

      • Rich Freshman

        Zach you are both a gentleman and a scholar. I just hope to inspire the future of tailoring. Thank you for the kind words chief

    • Steven Santander

      Nice post Rich! I always prefer separates also, perfect for the upcoming fall weather. Great use of color, pattern and texture!

      • Rich Freshman

        Preciate that Steven. The fall has always been my favorite season to dress in. Time to pull out the knits and flannels my man.

    • TimL

      I like the guy’s story and look but I think it’s tacky to walk around with a tape around your neck unless your in you work setting.

    • levijyron

      This guys looks good. I mean, really good.

    • John B

      Separates and especially DB jackets? Sign me up, especially for the plaid ones! Well done!
      Dan steals the show with his look in the last instagram post though!

      • Rich Freshman

        John, Dan’s always stealing the show. That man is one sharp cat. We play no games over here. Lol. And yeah man, plaids are huge right now, and the DB is back!

    • Hugh

      The light on the final photoset, beautiful Alex.

    • whowouldaguest

      All of these “unique” stories are starting to sound the same.

    • Karen King

      Nice job young man! You really got some good taste and wearing it well. Keep up the good work!

      • Rich Freshman

        Karen thanks as always for the kind words of support.

    • cam

      Dan, with regards to tailored separates, in what environment do you feel it’s ok to wear them versus a suit needed? I suppose I’m asking if you feel the rules have started to shift in a corporate environment where a suit is the norm. I know it probably depends mostly on the industry and city etc. thanks

    • Sean

      Guy can really rock a DB! Hard to get that streamlined V-shape when I try to rock one.

    • TO

      This guy is AWESOME!! Love his designs, story is awesome. Totally dig his inspirations, great execution of tremendous style, proportions ore perfect, great use of colour. What more could I say! (There’s probably more :)

      • Rich Freshman

        My man, you are both a gentleman and a scholar. And you actually said pretty much all of it. Thank you for that. We’re just having some fun man.

    • LouCaves

      I dig the measuring tape as a subtle marketing tool/conversation starter. And the fact Mr. Freshman is partial to separates. Well done, sir.

      Thanks, TSB.

    • Miguel

      I really love this post, I’m for one mostly use suit separates, I like his story and personal style…but those DB blazers are on point, they’re my favorites.

    • Brady

      Tailored separates are always my favorite, just adds more depth to the look. Well done Rich!

      • Rich Freshman

        Thanks Brady. I agree about the separates… tone-on-tone can sometimes be a bit plain jane. Gotta be cooler than that man.

    • tommyjohn_45

      Man… really digging your style. wish you were on the East Coast!

      • Rich Freshman

        Thanks chief. I’m in NY every other month, call or email me so we can align our schedules. 3238348308 /

    • Nate

      Great post Dan and team. this guy’s style, attitude and ambition is inspiring. I’ll even forgive him the tape as an accessory, seeing as how it relates directly to his role.
      The jackets in looks one and three are killer, as are the trousers in one.

    • Shawn

      First and last looks are dope. Definitively enjoy reading posts like this!

    • Josh

      The first and last looks are impressive as hell. He definitely takes plaid separates to a new level. I’d love to get something made by him.

      • Rich Freshman

        Thanks Josh. Gotta love separates. If you would like to more about my process and how you can become a client, send me an email and let’s start the dialogue.

        Talk soon

    • CordsABitch

      Corduroy is just one of those fabrics that’s hard to tailor well. As evidence by the collar gap in look 1. Not his fault though, it’s just a tough fabric to work into the shape of a tailored coat.

      • Shawn

        Probably due to his arm position, no? In the first picture, where he stands more neutral/relaxed, the gap is much less noticeable.

    • Massimo


    • Dan

      I can totally relate to him. When I was 13 I wore my first collared shirt. I noticed girls talking to me more and that I had more confidence. Over the next year. I would become one of the best dressed people at my school. If it wer’nt for that shirt, I would probably still be wearing ill fitting clothing and sweatpants with everything

    • ftony

      Great post fly ass dude

      • Rich Freshman

        Gracias my man. It’s only getting better