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How to look good in newsboy cap

Dan Dynamic

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I just watched The Greatest Game Ever Played and noticed everyone looked good in a newsboy cap. I thought this had to do with layering, the fuller cut and the choice of material, in other words a more vintage look (?). Compared with David Beckham, it just looks weird. At least, that is my opinion.

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Is it possible to look good in a newsboy cap without looking too customey, and if so, how? I am not sure if it would be appropriate to wear Shia's outfit today, considering the risk of looking like a neckbeard.
 
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rjc149

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If you're worried about looking costumey or like a hipster (or a "neckbeard"), wearing a newsboy cap isn't going to do you any favors.

If you're not worried about looking costumey or like a hipster, and you like newsboy caps, then wear one.

Choosing to wear a particular garment or style of garment will always pit these two approaches against each other -- "What is the image of myself I am presenting to others by wearing this" vs. "if that image is undesirable to me, do I like this garment enough disregard that undesirable element."
 

Dan Dynamic

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If you're worried about looking costumey or like a hipster (or a "neckbeard"), wearing a newsboy cap isn't going to do you any favors.

If you're not worried about looking costumey or like a hipster, and you like newsboy caps, then wear one.

Choosing to wear a particular garment or style of garment will always pit these two approaches against each other -- "What is the image of myself I am presenting to others by wearing this" vs. "if that image is undesirable to me, do I like this garment enough disregard that undesirable element."
I see your point and it is completely valid. I don't wanna base my outfit on one accessory, I want it to be a complement to my outfit.

However, I have grown tired of wearing baseball caps during bad hair days which is why I wanted to try something else. I am not sure simply exchanging my baseball cap for a newsboy cap would look good with my current wardrobe (workwear/ivy league). I really have no worries looking customey, but at the same time I wonder if Shia's look could be done in a more contemporary way by playing with material, cuts, fabrics, and layering (or lack thereof) - in other words, what are the fundamentals needed to look good in a newsboy cap? When would a newsboy cap be a flattering complement to my outfit? I figured it could be good to know the rules before experimenting.
 

bicycleradical

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I see your point and it is completely valid. I don't wanna base my outfit on one accessory, I want it to be a complement to my outfit.

However, I have grown tired of wearing baseball caps during bad hair days which is why I wanted to try something else. I am not sure simply exchanging my baseball cap for a newsboy cap would look good with my current wardrobe (workwear/ivy league). I really have no worries looking customey, but at the same time I wonder if Shia's look could be done in a more contemporary way by playing with material, cuts, fabrics, and layering (or lack thereof) - in other words, what are the fundamentals needed to look good in a newsboy cap? When would a newsboy cap be a flattering complement to my outfit? I figured it could be good to know the rules before experimenting.

Perhaps you could try a flat cap instead of the newsboy cap?


Some of those could work with your style. I have a couple of things from Lock and Co and enjoy them both.
 

Dan Dynamic

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Perhaps you could try a flat cap instead of the newsboy cap?


Some of those could work with your style. I have a couple of things from Lock and Co and enjoy them both.
Thanks for the suggestion. I have thought about flat caps but I never really liked the shape of them. Perhaps I should reconsider.
 

Mercurio

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I have to cover my head from the sun as per dermatologist instruction, so I wear flat caps very often, as I feel more comfortable with them than with baseball caps or with proper hats. I believe that the newsboy cap and its fuller cut make a different statement.

d38b5291-94bc-46df-8838-85c91c1d41de-jpeg.1602190
 
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Dan Dynamic

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I have to cover my head from the sun as per dermatologist instruction, so I wear flat caps very often, as I feel more comfortable with them than with baseball caps or with proper hats. I feel that the newsboy cap and its fuller cut make a different statement.

d38b5291-94bc-46df-8838-85c91c1d41de-jpeg.1602190
Nice. I also agree with you.
 

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