And luckily, we hit the jackpot at Gap Factory ... With an oversized silhouette and button front, you can easily transition this shirt from day to night. Wear it tucked into tailored trousers ...

It seemed like it flared out a little toward the bottom, but it might have just looked that way because the buttons threw off my sense of the balance of the shirt. My last stop was at Gap.

It’s what we like to call rich mom style, and right now, Gap is delivering that exact ... Espresso Run Shirt: This cropped button-down brings structure and volume in the chicest way.

Gap’s tees offer some of the best value ... from an undershirt that’s tucked in and covered with a button-up, polo, or other shirt. The neckline is also dependably flat, which is another ...

Snag similar tops from $11 at Amazon, Gap, and more Rob Kim / Getty ... consider channeling one of Gaines’ more casual shirt styles with this laid-back denim button-down from Amazon.