I've never liked boat shoes, doubt I ever will. Honestly in the summer, I just wear flip-flops 24/7. I don't care if it's not fashionable, I love them (and summer in Seattle is 2 months long).
Naked & Famous are highly recommended in this thread because of a number of reasons: lots of style options, great fit, quality construction and perhaps the biggest reason, extremely affordable price point.
Nudie is alright but they're definitely not my favorite. What's your price range like? Also what style of jean are you looking for? If you can afford them, brands like Momotaro and Pure Blue Japan are some of the best you can get. Below that (price wise) I'd reccomend Naked & Famous and 3Sixteen. On the cheap end (below $100) the only thing you should pay attention to is Unbranded (which is actually made in the same factory as APC, believe it or not). Hope that helps.
I know what you're trying to say, maybe 'gay' wasn't the right word. Perhaps, uncomfortable? Stiff? I know a lot of guys who refuse to tuck in their shirts cite the "I don't want to look like I just came from work" excuse.
While I'm fully on board with #teamtucked, there are definitely situations where an untucked shirt looks better. It really depends on the cut of the shirt and the outfit.