This pairing of a waistcoat and chinos couldn't possibly come across as anything other than outrageously sharp and effortlessly smart. Take a more casual approach with footwear and introduce dark brown leather casual boots to the mix. Loving how great this one is for transitional weather. As you're transitioning from your 20s to your 30s, you probably want to start dressing maturely. If that's the case, ensembles like this prove useful as a source of inspo.