For an effortlessly sleek look, consider teaming a grey plaid double breasted blazer with a black turtleneck — these pieces go really well together. Black leather derby shoes are an effortless way to infuse a dose of sophistication into your outfit. So so as you can see, it's a dapper, not to mention season-appropriate, combination to keep in your seasonal rotation. As you're moving through your late 20s, you probably want to start dressing maturely. In this case, inspo like this comes in very handy.