To pull together a laid-back outfit with a fashionable spin, make a crew-neck t-shirt and shorts your outfit choice. To bring a bit of fanciness to this ensemble, complete this ensemble with a pair of brown leather desert boots. When it comes to dressing for awkward transition weather, nothing beats a cool look that will keep you comfortable and looking your best. This combination illustrates how to keep killing it in the casual style department as a 30-something Millennial gent.