When looking for a baggier tee, search for phrases like "oversized" or "relaxed." If you get a slim-fit shirt a few sizes too large, you'll end up with something long and narrow, which has a high danger of looking dressy. You want something with a broader body and a looser fit in the sleeves.
In fact, to emphasise that your big T-shirt is a stylistic choice rather than an accident, you might want to wear jeans that are even skinnier than you're used to (without crossing into nut-busting area). A baggy T-shirt paired with baggy pants might make you look like you haven't changed your style since 1995, or even worse, like you've degraded into full-on Adam Sandler territory.
A little of old-school athleticism is put right into an enormous tee. So don't wear it with your most expensive wing-tips or loafers. Instead, go for a Sportscore vibe with a pair of your crispest, trendiest kicks. It'll make you look ready for anything, whether you're sprinting to the gym or avoiding photographers.
Go Vintage (and Rock On)
Band T-shirts from the late '80s and early '90s (think Metallica, Pearl Jam, Soundgarden, and Nirvana), like most clothes in the shoulder-padded suit era, were cut wide. These days, the worn-in graphics get you points with rock fans, and the easy-going fit comes will look as relevant as ever. That means it'll look less like you're trying to make a style statement, and more like you've just got a soft spot for angsty music.
It's an age-old concept to dress the way you want to be seen in society, not just for yourself. However, what you wear now determines your level of confidence
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