If you want to look cool when wearing the pair of hipster glasses, I strongly suggest you to wear a hat which will make you look so cool and handsome. You could also wear the clothing more like the hipster style. The whole effect will be so attractive and modern. Hope this help.
Hipster glasses usually match some free-style clothes. You shall avoid to wear business suit and some fashion style clothes. You can wear clothes in many ways. For example, you can wear T-shirt, shorts, slipper, worn out jeans. You can even wear sports style clothes. Besides, you shall avoid to wear some tight style clothes. You shall try to wear some loose style clothes.
As far as I know, hipster glasses are similar to nerd glasses in shape. So, I myself think they are amazing and could make you appear to be cool. So, here I can recommend that maybe casual clothes could fit your glasses, not suite or lady dress. I see a lot of people wear hipster glasses in casual clothes, jeans and sports shoes, that is awesome. Why not give it a try?