How Can I Develop This Look?

[Xenu]

I'm wondering if some of you could help me flesh out a style that I'd like to put together. I'm thinking of something that's a blend of artsy, nerdy, Bohemian, and beach bum. Below are a couple of photos that have hints of what I'm going for: the first one has the artsy/nerdy vibe to me; the second one looks kind of like a beach bum or possibly Bohemian.

What would you do to expand on this and blend these together? What sorts of pieces would you look for? What brands?

 

[Anachronist]

Steal some of Grandpa's old underwear, pillage an old clothing collection for jacket and trousers, put the stuff on, sleep in it and wear it with pride the next day, preferably after the consumption of enough dope for a relaxed look

Joke aside: this look is okay for a beach or pool party in summer or maybe to a club/disco, but apart from that there's hardly a place you can pull this off without bordering on looking sloppy (which I do understand is the rebellious intention of this look, but perception is reality). It is pretty simple to put together: find yourself some chinos or shorts in light khaki or non-denim colors (be bold here and go with unusual colors such as red or green) and choose shirts and jackets preferably made of or with linen as these create a crumpled and very relaxed look quickly. No socks is the motto, you may even want to roll up the hem of your trousers to show a bit of ancle (linen trousers are an option too) and shoe wise I'd probably choose canvas sneakers or boat shoes. Get yourself a light straw trilby hat (narrow brim, err on the smaller size), unbutton the top 2-3 buttons of your shirt, grab yourself a drink and have fun

Personally, I'd stay away from wearing undershirts like in the first picture because I just think this is just the step too far into making a joke of oneself, but this is just me. If you have the guts for this, do it by all means and see how it is perceived. A better choice might be a striped sailor's T-shirt à la Jean-Paul Gaultier, but it helps to have a bit of muscle to make that one look good... see an example here: https://www.hallensteins.com/clothing/tops/t-shirts/kit-sailor-stripe-t-shirt-8939837?c=BLUE/WHITE

Hope this helps for a start!

 

[Jan Capek]

I am going to be even less helpful than Freund Anachronist. Why would you want to imitate someone else's style? Don't you know that "when two do the same, it's never quite the same?" Don't you know that being a Bohemian or a nerd is not a result of a conscious decision? There is a chance that the styles of these two lads were shaped by their upbringing, self-esteem, position in society (self-perceived or otherwise). The first one might (or might not) suffer a low self-esteem, the other may (or may not) be gay. What if both of these guys play 10 musical instruments each, while you are an IT specialist?

There is nothing wrong with seeking inspiration in the outside world, and it is indeed a sign of being cultured to actively learn about human achievement in various areas (be it food, coffee, tailoring, fine arts...) and to refine one's knowledge and taste, but why copy anyone?

Still, if you insist, it would be helpful to state where you live so that other members can give you concrete tips. Generally, you should try the indy shops found on those eclectic, "artsy" streets any big city offers, or attend social functions the objects of your interest frequent. Ask about and in no time you will know all their secrets, and make friends.

 

[Xenu]

Both great responses. Thank you. By the way, I live in Minnesota, so this would definitely be a summer look for me.