A big issue I see with the average man's style is immaturity.
Baggy jeans, hoodies, ball caps...most guys in their 30s still dress like they're in high school or college...not good.
Here are some quick pointers on how to mature your style without making you look "old"...
First, upgrade your flimsy zip hoodies for luxe options in cashmere or fine wool. Wear these hoodies straight up on their own with your denim jeans and chinos. Go for a nice FITTED look like you see on the right.
Second - your jeans should be dark and fitted. Avoid anything excessively baggy or with stylized back pockets which lean more youthful and trendy.
The one exception here would be something like a pair of Levi's - their back pockets have a design but they are within good taste.
Third - if you're going to wear a ball cap go for a higher end, PLAIN option. The ball cap you see on the right is in a wool/cotton blend with a subtle check pattern (perfect for the fall/winter). This is what a grown man's baseball cap looks like.
Fourth - mesh style sneakers should be tossed in the bin and replaced with full grain leather, leather lined sneakers instead. These will look 100x better with your jeans. Mesh sneakers are better for the gym or your athleisure fits (when you know what you're doing).
Fifth - I get that you are a diehard fan of <insert sportsball team here> but aside from when you're watching the game I recommend sticking to PLAIN t-shirts for casual styling. It's a cleaner, stronger, more mature look.
The sad news is that the immaturity you see with most men's sartorial choices runs much deeper in their lives...it is in fact all pervasive. Men in their 30s today not only LOOK less mature then their fathers/grandfathers when they were the same age but they ARE less mature too.
Dressing like a grown up probably isn't the silver bullet here but it is surely a step in the right direction. When you start dressing like someone who has his shit together you're in essence pulling your own psychology towards maturity and real adulthood.
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