Five other finalists from more than 900 entries joined the 25-year-old and they attended a styling session, professional photo shoot and dinner in Auckland.
"It was such a good experience for me as I have wanted to do something in modelling for a while but I still never thought I would win it."
Weeks later Mr Hobson received the call that he was crowned New Zealand's most stylish and confident glasses wearer.
"It has literally gone from the announcement to almost boarding a plane. I leave on Saturday, I cannot believe it."
The most exciting part for Mr Hobson is meeting his celebrity idol and discussing what frames work best with certain outfits.
He has always taken real pride in the way his specs express his individual style and how they work to compliment what he is wearing.
"When the time comes to buy a new frame it is a huge process, it takes me three to four hours in the store then another day showing friends. I can't wait to hear what she thinks about dress style according to frame."
According to the star judge and competition ambassador, Kim Cattrall, Mr Hobson stood out as the overall winner as soon as she saw the finalist photos.
"Brian's charming and quietly confident personality really comes through from behind his frames and I love his classy look."
She said he was just what they were looking for in the search, as his personality shone through as soon as he put his specs on.
"It's going to be great to spend time with Brian in New York. As a proud spec-wearer myself it's been great to see so many people who make their specs the ultimate fashion accessory."