I Only Want to Wear Button-Downs Right Now (& These Are the Best Ones)

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I was surprised when the edit team asked me to write this story, unaware I had developed a reputation as an aficionado of the button-down shirt. As I sat down to write, though, I realized that my ardor for these shirts had grown over time, without my even noticing it—basically, it’s the plot of all the best love stories. 

Here’s where it starts: When I was a child, my mother drilled into me the importance of keeping your shoes shined and having a smart coat. Maybe this is an English obsession—this longing to look “smart.” Carrying anything (besides groceries) in a plastic carrier bag was forbidden. Smart—never sloppy or schlumpy—was always the goal. 

The other factor is my weight. Throughout my adult life, it’s fluctuated up and down, along a 50-pound range. Sometimes I can wear my most beloved garments—and sometimes I can’t. By this point, I’ve developed a filing system of “too small right now” and “too big right now.” My most cherished items are the ones that I can wear at both ends of the spectrum, and oversized button-down shirts fit firmly in this category. (Along with Pleats Please and Chantelle Soft Stretch Underwear, which are also the shapeshifter’s friend.) Now, in my sixth month of pregnancy, I’m experiencing an entirely different kind of weight gain. I’m now at the point where I’ve maxed out even my biggest pants, but the button-down shirts still fit. 

Pregnant or not, I still maintain that the button-down shirt may be the most valuable player in your work-from-home wardrobe. If you’re shopping right now, adding a button-down to your cart can provide flexibility, comfort, and pizzazz in one, tidy package. (If you’re not shopping presently, I bet you have one at the back of your closet that’s due for a reevaluation.) Here, some advice for how to style it like a pro.

The First Date

My shirt obsession started with Phoebe Philo’s Céline. Here was a silhouette that looked smart, comfortable, AND fashionable. I was hooked. 

I purchased one at a Barney’s sale: oversized and white. I wore it at least once a week, with narrow black pants and sneakers—mostly Stan Smiths or slip-on Vans—for Phoebe’s entire 10-year tenure. I added similar styles from Cos so I could give my prized shirt the day off.

Phoebe styled the humble shirt with pants (of course) and as the foundation to a suit, but also in more unexpected ways—with the shirttails peeking out from under a mini skirt or as the underpinning to a short, sleeveless dress, making what would have been merely a sexy LBD suddenly more intriguing. In case you need further evidence of the powers of a button-down shirt, I present to you, 50 ways to style a shirt, courtesy of Phoebe Philo. 


The Rose Ceremony

After Phobe left Céline, I searched for a new look. Around that time, The Gentlewoman profiled a pregnant Martine Rose in her London studio, and I knew I’d found my gal. (This image of Martine, beautiful and smiling with her pregnant belly peeking out from her sweats, remains burned into my memory.) I was working for Outdoor Voices at the time, and Rose’s sporty, genderless collection, with a little twist of English humor, felt completely aligned with how I wanted to look.

Martine Rose’s Spring 2018 menswear collection was inspired by Canadian photographer Trevor Hughes. I became obsessed with his photographs of bike messengers and bookmarked half the collection in ShopStyle, waiting for my favorite pieces to be reduced. Come sale time, my main score was the pink shirt from look #19. If you know me, you have seen this shirt a hundred times—I wore it mostly with biker shorts or with something sporty (like Patagonia Baggies or an Exercise Dress) underneath. Most recently, I’ve been wearing it with these Juliet Johnstone pants. You can find other shirts like this pink one for a similar look.

The Perfect Shirt for a Zoom Call

As my pregnancy progresses, I’ve been reluctant to shop. Not only because we’re in a global pandemic and shopping feels different, more loaded now, but because maternity clothes don’t appeal to me. (Maybe I haven’t found the right maternity brand? Please tell me in the comments if I’m missing a trick here!) I’ve slowly watched my wardrobe get whittled down, as my belly outgrows everything. 

Thankfully, this shirt from Kwaidan Editions—the last of my pre-pandemic purchases—is still serving me well. If you’re a regular Man Repeller reader, perhaps you’ve seen it before, here and here. The strong color and interesting collar make it exceedingly Zoom friendly. I’ve mostly been pairing it with sweats during WFH hours or just underwear and socks for some big Risky Business energy.

The European Vacation 

As we approach Memorial Day with non-essential travel off-limits, I’m looking for a sartorial vacation in a shirt. I have my eye on these Jacquemus options, which feel like two weeks island hopping in the Mediterranean with Luke Edward Hall

‘La Chemise Soleil’? Don’t mind if I do.

Tiffany Wilkinson

Tiffany Wilkinson is Man Repeller's Creative Director.

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