Confidence is entirely relative. I always made a point of following Woody Allen's advice that 80% of success is showing up, but once I got there I didn't always seize opportunities as best I could. For example: I did the Milan and Paris menswear shows for three or four years in a row, but it wasn't until my seventh season that I got up the guts to go and interview all the industry guys who'd been my heroes for years and years. When I did, I kicked myself for not doing it earlier – not only did I realise how approachable people are, but the contacts I made were instrumental in my moving to New York and getting a lot of the work I'm doing now.
For as long as I can remember I've had a silly tendency to put people up on pedestals – especially those people whose work I admire. When I'm a fan, I want to know everything about someone (I'm that guy). So I'd be in positions where I'd get to meet one of my heroes and I'd literally know the freakiest details about their lives, plus every single piece of work they'd done since the beginning of their career, and I'd overthink the situation and end up being too nervous to make conversation or a good impression.
At the risk of sounding cringey, people often ask me why I'm friends with so many models. The answer is simple: They were the only other guys who were a similar age to me at the shows, and they were always far easier to talk to than any of the pretentious fashion people on the scene.
In this industry you do sometimes feel like the only way to succeed is by getting in with the cool crowd, and it's true that networking goes a long way. The main thing to remember is that people aren't nearly as intimidating as you imagine they'll be. At the end of the day, we all have the same hopes, fears and insecurities, and I've seen the most successful menswear guys get all nervous and adjust their clothes in the hopes that Tommy Ton or Scott Schuman will take their picture – just like an intern would.
The most important thing is to be friendly, to work hard and to tirelessly pursue your ambitions. Insecurities are self-imposed and you're better off getting rid of them, it's as simple as that. Also, a smile goes a long way. Shyness is often misinterpreted as rudeness, so you're better to be cute and quiet than cool and aloof.
* I used a photo of Hedi Slimane on this post because by all accounts he's an incredibly shy person who has had an insanely successful career in fashion.
Best of luck!
I LIKE YOU!