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Tommy John's underwear is praised for its comfort and fit, especially highlighting the smooth waistband that doesn't feel too tight. The speaker emphasizes the enjoyment of wearing these undergarments, describing them as a luxury that enhances the overall sleeping experience. The softness and fit are touted as reasons for their preference, indicating that wearing quality products makes a difference in personal comfort. There’s a playful tone that conveys a strong personal affinity for the brand, suggesting that these items contribute significantly to comfortable living.