About me: Rupert Trendall

My story

I’m Rupert Trendall. My style journey began in the mid-2010s. Up to that point I had never been happy with the way I dressed and decided to do something about it. Over the next few years I hit the high street, the books and the internet, learned all I could about men’s style and became totally hooked on the endeavour. Once I had my eye in I found that dressing well brought me great deal of happiness and was a no small boon to my mental health and self-confidence. Both of which I have always struggled with. 

One day I realised I had likely learnt enough to turn professional, could help others with their style aspirations, and share this joy that I had found. And that’s precisely what I did, launching OutSmart in 2017.  

Prior to, and in the early days of my styling career, I worked in the events industry as a steel-climber, stage-builder and crewman. Building everything from small corporate events to major music festivals. Personal shopping makes quite the contrast from a day’s work spent harnessed to a structure, thirty metres in the air, swinging a hammer against cold steel. I do miss the old work but the new is very much more comfortable and rewarding.

Also prior to and in the early days of my styling career, I was a high-functioning alcoholic and substance addict. I eventually attained sobriety in 2019 but that was on the backdrop of a mental health crisis. A depressive episode so severe it robbed me of the ability to attend to my styling career. At that point I put the business into indefinite hiatus and pursued other business interests, until the relaunch of OutSmart in mid-2022. I remain content and steadfast in my sobriety and my mental health is much improved. 

Outside of styling I am a dedicated weightlifter, terrible runner, extremely keen hiker and aspiring alpine mountaineer; all of which are also very helpful for one’s mental health.