How do I begin to break away from the traditional shirt/pants/shoes/sometimes

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Start off with items that are wacky in a subtle manner (seaming, print/fabric, pocket placement, other small details) that can slowly and easily be introduced into your current wardrobe. One strange item can be balanced out/accentuated with an otherwise normal outfit, and tops are usually the most interchangeable item in someone's wardrobe. Don't get anything you don't 100% love, and maybe try thinking of at least three outfits you would enjoy wearing before you pull the trigger on something. Over time you can slowly up the ante as you grow more comfortable with weird clothes and further expand your personal style.

Pic related is kind of an example, the rolling stones print could be considered too extra for regular men's office wear but it's balanced out with simple pants.

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>>12400076
Another example, a dramatic jacket worn with a simple shirt and jeans.

>>12400085
that's pure autism, the outfit needs to make some bit of sense

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Could start working things that are considered odd like high waisted trousers, double denim or overalls. Because menswear is so simple you don't have to do much to seen as experimental.

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>>12400085

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>>12400135
Then you can slowly move into ridsnap/Tokyofashion levels of crazy

>>12399963
just wear a dress, missy.

>>12399963
>Men's fashion feels incredibly restrictive in terms of what's practical and socially acceptable
you are straight up wrong
the restrictions are in your head

>>12400142
literally just a hoodie and cargo shorts tho

>>12399963
Go full ricky

>>12400142
was this the inspiration for Sora in kingdom hearts?

>>12399963
I feel the same way and you're not going to find any helpful information on this shitty board. Just go out and try different things and if they don't work, then you've learned something. If they do work, there you go. That's just about all you can do