Wear a crew-neck t-shirt with grey vertical striped chinos for a fuss-free menswear style that's also put together. Black dress boots will give an element of class to an otherwise too-common ensemble. If you're looking for a stylish winter-to-spring transition outfit, this is it. As you're getting to your 30s, you want to start dressing more professionally. If that's the case, getups like this are a never-failing option.