Why not try pairing a shearling jacket with a white and black crew-neck t-shirt? Both of these items are super comfortable and will look great when matched together. Dark green suede loafers will give a touch of sophistication to an otherwise simple ensemble. A cool outfit that will take you from summer to fall like this one makes it very easy to welcome the new season. After 30, you want to start dressing like a grown man. In this case, ensembles like this are perfect as inspiration.