Reccomendations for styling a stocky build?

Often get told I have a stocky rugby player build by relatives and my dads work friends because i have big shoulders/arms and im a tad chubby. Have always thought my fashion sense was lacking a lot but I'm not sure what would look good on me and too scared to be aimlessly trying on clothes alone in a store. Usually I wear just a hoodie or polo and black jeans. Looking for affordable fashion with a budget of about $300. Also round or square framed glasses for my facial structure?
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