Cutler often sported basic T-shirts paired with jeans, embracing a simple, everyday look. He wasn’t typically seen in flashy or trendy outfits.ot!
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Especially in colder months, he could be seen wearing plaid or flannel shirts, which added a more rugged and relaxed vibe to his style.!
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He was often spotted in casual hoodies or sweatshirts, especially when attending practices, games, or informal events. This added to his reputation for dressing comfortably.
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Cutler was frequently seen wearing baseball caps, especially during his time in Chicago, fitting in with the sports-casual aesthetic
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When attending more formal events, Cutler would wear well-tailored suits, though even in these settings, he maintained a relatively conservative and simple style compared to other athletes.
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