If you gravitate towards laid-back combos, why not consider this combo of a grey crew-neck t-shirt and grey skinny jeans? Put a different spin on this outfit by sporting a pair of dark brown leather casual boots. Many people suppose that just because you need to get bundled up you have to sacrifice good style, but it's just not true, and this look is proof. Dressing inspiration like this will help you stay incredibly fashionable as you progress through your 20s.