Pair a black and white plaid long sleeve shirt with charcoal jeans for a stylish and easy-going look. You can get a little creative when it comes to footwear and introduce a pair of black suede chelsea boots to this look. As you can see here, it's extremely easy to look sharp and stay comfy when chillier weather comes, all thanks to looks like this one. This outfit should encourage anyone who wasn't sure about relaxed dressing over 30.