Functionally Fly feat. Jason Andrew

February 5th, 2015

As much as I love a story about an emerging menswear designer, style editor, or custom clothier, I find this one even more inspiring.

Jason Andrew doesn’t work in fashion, although people often assume he does based on his impeccable style and taste in menswear. Instead, he works in hospitals and the homes of sick people who need his help. He’s a speech pathologist with two degrees currently working on his doctorate who works with autistic children, cerebral palsy patients, and stroke victims who have difficulty speaking.

We first met Andrew at the Liberty Fairs show, where he stood out from the style crowd with one of the best outfits in the joint (check out #7). After the show we linked up on a cold and windy NYC day to share a little more about his style and story, and how the two interact.

    On Learning from London

    mensstylejasonandrews (1 of 16)

    “I was raised in London. Early on I learned the foundations of menswear and the value of dressing well.

    The first thing I learned was the importance of using clothes as a uniform to be taken seriously in a professional setting. After showing up to work in a ‘casual cool’ blazer-over- t-shirt, my first boss asked me: ‘Did you come to work today?’. He taught me that if you’re not carrying yourself a certain way (in this case, dressing in a proper shirt and tie) then you weren’t going to be ready for success or taken seriously by your patients/clients/peers.

    When I came to NYC it seemed that everyone was more into sneakers, logos, and brands. There was little focus on fit or longevity of design – things that I learned were most important in London… Also in London the idea of mixing high-end with low-end is right there in your face. You have Asos and Topman right next to Selfridges and Savile Row. I found that the best-dressed men usually mixed and matched from both.”

    mensstylejasonandrew (30 of 1)mensstylejasonandrews (2 of 16) mensstylejasonandrews (3 of 16)

    Another classic London move: protecting fine leather shoes with rubber galoshes in the rain or snow.

    mensstylejasonandrews (4 of 16)

    • Wayfarer Sunglasses by Persol
    • Blackwatch Suit
    • White Button Down Shirt by Gitman Bros.
    • Black Turtleneck by Polo Ralph Lauren
    • Black leather gloves by Polo Ralph Lauren
    • Watch by Raymond Weil
    • Shoes by Magnanni
    • Rubber Galoshes/Overshoes by SWIMS

    On Fit & Function

    mensstylejasonandrews (6 of 16)

    “As a result of my athletic 6’4″ 240 lb frame I have difficulty finding the right fit off-the-rack. Mainly, the length of shirt sleeves (longest available is usually 35″, while I’m closer to 40”) and the fullness in the trousers in the thighs. For these reasons I have an affinity for brands like Club Monaco and other diffusions of Ralph Lauren, because they usually give enough allowance to let-out their garments at the tailor.

    Once you find the right fit, in my opinion, style all comes back to function. It doesn’t make sense to have a necktie getting in the way when I’m feeding an old man who recently had a stroke, for example. And I might intimidate some of my south-side Jamaica Queens patients if I show up in a suit looking like a government agent… Knowing your audience and choosing clothing that is functional for your environment are the first keys to dressing for success.”


    mensstylejasonandrews (9 of 16)WesDB (1 of 1)

    • Teardrop Fedora by Bailey’s of Hollywood
    • Navy Double-Breasted Blazer by RL Purple Label
    • Cutaway Collar Shirt by Kamakura
    • Aviator Sunglasses by Persol
    • Gloves by Brooks Brothers
    • Tie by Gitman Bros.
    • Green Double Breasted Overcoat by Club Monaco
    • Wool Herringbone Pants by Club Monaco
    • Chelsea Boots by Magnanni

    On Style & Perception

    mensstylejasonandrews (11 of 16)

    “Dressing well is about being a man and taking care of responsibilities. It’s about consistency and continuity in everything you do. Your style can make people trust you and believe in your ability as a professional…

    Interestingly, though, it can also have the reverse effect. Going too hard, or being too flashy, can be off-putting in a professional setting (especially a medical setting). In some cases people might think that you take dressing too seriously, or that you care more about looking good than being a professional and performing at the highest level.

    I see many different perspectives, because I work with young children as well as older patients and medical professionals. With children, style can convey authority and keep attention. Kids often think my style is “cool”, so they want to listen to me because they want to be like me. It’s an effective tool. However, I find that some of the more seasoned medical professionals in the hospital can be skeptical of an overly stylized outfit, as it if takes away from my focus or ability to do my job… It’s like the first-year Wall Street banker who shows up in the full Gordon Gekko kit, and gets sent home. In the workplace, some things have to be earned with age and experience.

    In the end, what’s most important about dressing is knowing your audience, and your perception within that audience. Style is a very effective tool, but it’s up to you to use it to your advantage.”

    mensstylejasonandrews (15 of 16)


    mensstylejasonandrews (16 of 16)mensstylejasonandrews (14 of 16)

    • Teardrop Fedora by Bailey’s of Hollywood
    • Sunglasees by Ralph Lauren
    • Faux Fur Collar Overcoat by Gant Rugger
    • Cable Knit Shawl Belted Cardigan by Club Monaco
    • Cutaway Collar Shirt by Kamakura Shirts
    • Watch by Raymond Weil
    • Moleskin Jeans by Polo Ralph Lauren
    • Chelsea Boots by Magnanni

    Thanks, as always, for reading.

    Yours in style,

    Dan Trepanier

    Shop Custom Menswear Made in America


    Take me to the Shop

    • disqus_jm3MdOCAo4

      Wow, this is one of the best posts I’ve seen on this website. I have been reading this blog for the past 4 years and this is the first article that compelled me to post. Two quick comments
      1. Jason, whats your shoe size ? Looks like you are a 13 / 14 which works well for Magnanni because they carry larger sizes (I am a 14)
      2. Dan, wanted to commend you on the great work you have been doing on this website ! One of the best style blog on the web.

    • Terrified T

      Those tight armholes though… phew, do not look comfy.

    • Agentslife

      Great Job,
      I’ve known Jason for a few years and watched his sense of style grow over time. We always share ideas and our views on fashion trends and life. It is good to see him getting the shine he deserves.

    • Jack

      One of the best posts on TSB/AOS.

    • Das Chaussures

      One thing I love about this site is that is features different ethnicities. It’s truly about style. But why is it important to feature different ethnicities? It helps me to vividly imagine myself wearing these outfits.

    • Ishandev

      I see myself wearing everything in this post. That’s the highest compliment I can think off. ;)
      What’s up TSBmen crew? Six pack Dos Equis aka Ishan

    • Unseen Flirtations

      One of the most important features on this site. The philosophy of form and function and genuine purpose of style is rich food for thought. What I love about this is the humility of style he displays, while expressing himself through thoughtful style choices. It’s not dandyism, but it stands out, for the right reasons. It’s a life lived well

    • Dave Coakley

      Flawless. Great attitude towards it all too.

    • MaleStylePro

      A great example of using accessible brands to create interesting and well put together looks. The second look is my favourite, even though I own the same suit in the 1st image. I agree with you Jason, that you should know your audience. The colours and hues of the second look, demonstrates your keen eye for details. Well done.

    • Randy

      Excellent post! Effortless style from Jason and appreciated his commentary on dressing professionally and for your audience.

    • Jason Andrew

      Appreciated Miguel.

    • Jason Andrew

      Thanks a lot Eddy.

    • John

      Jason, who’s your tailor?

      • Jason Andrew

        I use my grandfathers tailor. Just a little old gentleman who works in his basement.

    • Jaytonb

      Oh Dan, autoplay video ads? For shame.

    • Jeanscuffed

      This dude KILLS!! I’m not gonna lie, after seeing his outfit on the Liberty Fairs post, I tracked his Instagram to see more fly shit. The first outfit of his with the SWIMS just pops! His style is definitely inspiring and just screams Risk Taker. Job well done Jason and Alex for his photography!

    • Matt

      What’s even more noteworthy is that this is not another “blogger” or “sartorialist” or any other vain street style zero but a guy who actually is Someone and does something meaningful for a leaving.

      • Jason Andrew

        Humbled by your words Matt.

    • JohnnyK

      Love this guy because he buys clothes from brands that we aspiring style aficionados actually shop at. Club Monaco, Ralph Lauren, Kamakura. Keeping it pragmatic. Definitely going to check out some pants from Club Monaco now.

    • TimL

      Wow…. great looks all around.
      Love look number 3. So amazing and natural.
      Also… props to Alex for great background and photo work
      Best post I’ve seen in months!!!

    • Jason Andrew

      Thanks Adam.

    • Jason Andrew

      Thanks man. Invest in a pair perhaps green or blue you’d not be disappointed.

    • Ben

      Fantastic outfits, and a well-considered approach to dressing well within the real world. I also love the use of colour; the greens and oranges really compliment your skin tone.

      Would be great to see more “real” people being featured! ;)

      • Jason Andrew

        Thanks Ben. I try to think about Sallie Mae before any purchase. I try to envision the use of an item long after a season passes.

    • Andrew

      A lot of inspiration here! I’m also 6’4, although a little bigger than 240 lbs. However, Jason and I have a similar frame. The dude has great style.

    • Shawn

      I meant “normal” as in “other professions than the big 3 we often see or hear in #menswear”. Hope no offend was taken, it was really meant in a good way.

      • tommyjohn_45

        Haha naw, just bustin’ your balls

    • Alex Crawford

      Thanks man!

    • TO

      Glad he mentioned that Club Monaco is good for thigh and other allowances, I have a pair of winter trousers from them being let out in the thigh right now at the tailor… More brands should do this, regardless of the cost of the “extra” fabric. Athletic-types certainly appreciate it! Good to know that RL does it often too, I will pay more attention to this now. Dude’s style is impeccable and lux, he layers like he invented it. Thanks AOS for this one!

      • TO

        Oh and Alex, the third shot in “On Fit and Function” is one of the most impressive you’ve ever done! Love that snap.

      • tommyjohn_45

        Yes! Very useful info. Will be checking these brands out more closely for sure.

    • cuponoodles

      Walked behind this dude at the Atlantic-Barclays subway a day or two ago. Had the same orange rubbers on over the black DBs at least.

      Nice looks!

    • Shawn

      Love the article, guy has a very nice style! I also appreciate the fact that he’s a health care professional (as I am, although I work with patients suffering from cardiopulmonary-based illnesses); we are often used to see features of CEOs, lawyers or some sort of designers. Nice to see that other people with “normal” professions can dress well too (if we can call two degrees and almost a doctorate “normal”)!

      • tommyjohn_45

        Designers and lawyers aren’t normal?

    • Miguel

      Great article,

      Love the work that he does but also love his style, he looks like he’s not even trying, great separates and combinations.

      • Dan Trepanier

        Thanks for the continued support Miguel!

    • eddy

      wow great post and one i can relate to. impressive outfits from top to bottom especially in an industry thats not so tolerant to good style without being considered too flashy. thumbs up man

    • AdamE

      Nailed it. Great example of great situational dressing (the art of always being the best dressed man in the room, but never appearing to be overdressed…). Some awesome pieces and texture play throughout the looks…
      Nice to see someone keeping it real nailing the looks without being overly peacocky…

    • tommyjohn_45

      Great looks, Jason. Great examples of stand out outfits without going overboard. Look two is my personal favorite. That coat/hat/glove combo on the navy blazer backdrop just pops. Love the texture of the pants too, especially with the perfectly tailored cuff.

      • Jason Andrew

        Thanks a lot, I like having fun with separates, letting the subtlety with texture and tones do the talking.

    • Papi Moscow

      Impeccable style. 10/10. Great to see someone on this blog whose not pushing an agenda just an extremely well dressed guy who deserves to be spotlighted.

      • Jason Andrew

        Thank you.

    • cam

      Holy shit…look 3 may be the best use of color and texture that I’ve ever seen on the site or anywhere for that matter.

      • Jason Andrew

        Humbled and very much appreciated.

        • cam

          hey jason, where did you get the tartan barn coat?

          • Jason Andrew

            It’s Polo deadstock now but go to Ralph Lauren he has a oilcloth version otherwise scour eBay. He’s made denim versions of the same coat as well.

            • cam

              thank u sir

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