This pairing of a navy crew-neck t-shirt and light blue ripped jeans is a safe bet for a ridiculously stylish look. To bring some extra definition to your look, complement your ensemble with a pair of black and white leather brogues. So as you can see, it's super easy to look on-trend and stay warm when colder weather hits, all thanks to outfits like this one. Laid-back ensembles for stylish 30-something guys aren't actually that hard, as you can see.