This sophisticated pairing of a double breasted blazer and navy dress pants will prove your sartorial prowess. For something more on the cool and casual side to complete this getup, introduce a pair of tobacco oxford shoes to this look. As you can see here, it's very easy to look on-trend and stay snug when fall arrives, all thanks to outfits like this. This pairing shows that after 40 you still have a wide range of dressing options.