Try teaming an olive crew-neck t-shirt with grey plaid chinos to create a laid-back and practical look. You can get a little creative when it comes to shoes and spruce up this outfit by slipping into derby shoes. So so as you can see, it's a knockout, not to mention season-appropriate, look to have in your transeasonal arsenal. As you slip into your 30s, you probably want to start dressing like a grown-up. In this case, getups like this become very relevant.