QUESTIONS FOR THE WOOSTER
Via The Sartorialist
You’re a fashion role model and Internet style icon, what do you think others see in you that has inspired this?
I can only imagine it’s because I’m willing to ‘go there’ and take chances. Getting dressed is really the only area in my life that I can say I am fearless; I’m terrified of so many things, yet am somehow not afraid to wear anything. For me, it’s always been rather innate. As a 5 year old I was specific about the way everything fit, even a t-shirt.
What do you find is the biggest challenge for guys who want to look good, but don’t know where to start?
Whenever it’s out of their comfort zone, guys need a blueprint– they have an event: what do I wear? They’re going to a black tie: what does that mean? They’re going to meet their in-laws: how do I impress? I think that overall guys are interested in acquiring a wardrobe based on problem solving; finding something cool that fits into their lives.
All the young bloggers geek out about double monk strap shoes and tailoring– very old school, traditional elements. Cool doesn’t necessarily mean avant-garde.
The thing that started it all was probably casual Friday; the thing that was supposed to be liberating fucked things up more than anything.
Are you now more aware of how you approach getting dressed every day?
I really don’t think about what I’m going to wear until I jump in the shower. However, I feel that the stakes are higher each time I make a purchase or decision about what I’m going to wear, because there are several chances that it will be amplified.
I like to take risks and not everything I wear is going to be everyone’s cup of tea. That also means I cart around gigantic overweight trunks, because I never know how I’m going to feel on a given morning. Airport check-in desks are the bane of my existence, absolute hell.
Has the amplified attention affected your self-esteem?
If anything, it’s made my self-esteem worse… I am my own harshest critic. As much as I love to wear something that’s a bit off, I’m terrified that I will be made fun of. It’s a frightening conundrum.
I love clothes, but as the season approaches I always feel the need to add new things. It’s natural because I have the opportunity to see more, which makes me want to buy more– a very expensive occupational hazard.
If I’m wearing something it’s nearly always because I bought it. I’ve certainly accepted things a long the way, but I never feel obligated to wear them. I have to intrinsically love something in order to wear it. I’m grateful to be constantly surrounded by many of the things I love.
Thanks to The Sartorialist