10 Occasions to Wear Your Best Shirt

An ode to that marvellous shirt sitting in your closet

BY

Published: 2 November 2025

1. The very next day. You’ve been quietly yearning for a shirt like this for a while, and now you finally have it. It broadens your shoulders and hangs off your back like no other shirt has before. It’s time to test out the fit.

2. On your birthday. It’s just dinner with your family—nothing too fancy. Your sister snaps a picture to remember the day you turned 26. It’s the first time you’ve been photographed in your best shirt.

3. Secondary school reunion. Intimidating. It’s been more than a decade since you last saw your classmates. You’ll need a confidence boost.

4. On a challenging day. You woke up crooked, the sun is blistering, and there are meetings upon meetings today. It’s going to be a bad one—you can feel it in your blood. You’ll need something to carry you through.

5. The first date. After seeing her at the reunion, you couldn’t help but ask her out to dinner to catch up. You’re a decade late, but you finally found the courage.

6. To the grocery store. You’ve been seeing her for a while now, and tonight, you finally decided to cook her that steak and egg recipe you’ve been talking about for months.

7. On your honeymoon. You’re spending the next few days in Versailles! It’s summer in Paris, and you need something breezy and easy while you walk slowly and eat cherries.

8. Housewarming party. Your shirt was just lying around, as it always is, but it no longer fits you like it once did. Your shoulders are broad enough now, and the shirt no longer hangs off your back the way it once did.

9. Your child’s first day of school. You wear the shirt without thinking. By the time you’re driving home with your wife, there are small wet patches on the bottom of your shirt.

10. For the last time. You won’t remember the last time you put it on, nor will you remember where you last left it. The goodbye won’t be grand. It’ll appear in photographs from time to time. An uncontrollable warmth will weigh heavily on your heart before settling into a dull ache. The feeling will show itself on your face with a smile, and no one will ask why.