The Case for Dressy Shorts, Thanks to Kate and Meghan
A look at why the summer style is having an elevated moment, what message it sends, and links to my favorite pairs.
Welcome to So Many Thoughts, a semi-weekly newsletter about royal style and the other parts of life I want to think through with you. You can subscribe here and follow me on Instagram at @EHolmes. Thank you!
Shorts scare me. There! I said it! No other category in fashion is as terrifying to me as shorts. I love them on *other people* but have largely avoided them myself. It’s mostly because of my own body hang-ups (cough my cellulite cough) that I’m actively working on unlearning. But also there are so many style alternatives. I have survived countless summers in breezy dresses and cropped pants.
My thinking on shorts began to shift when I became a mother, which requires far more crouching and crawling than anybody tells you. And then it shifted further when I moved to California, where summer lasts all year. Shorts became more appealing as a practical option; I’ve bought a few cut-offs to wear where the style stakes are low (like the beach and the playground).
But then, in the last few weeks, Meghan and Kate stepped out in shorts. Not casual shorts. Dress shorts, for work engagements. Both times I was delighted. These looks felt fresh—and fun. Cut to me reluctantly turning inward: Do I need to rethink shorts?
Tldr: Yes. Below you will find so many thoughts on shorts in three parts. First up is my own take on Meghan and Kate’s outfits, followed by my super stylish friend, former Wall Street Journal deputy fashion director Becky Malinsky, making the case for shorts (hint: they project confidence!). Finally, I faced my fears and tried on a few pairs in the name of research—and have some great picks for you.
What do you think of shorts? Or is there a category of fashion that scares you? Please hit “Join the discussion” at the bottom of this email and share in the comments of this newsletter.
A Long Answer to the Question of Shorts
I vividly remember the first time Kate wore shorts — because I happened to be in labor with my daughter. In between contractions, my phone was blowing up with the sight of the duchess’s bare legs. I still laugh about it! Three years later, shorts on a member of the royal family seem far less shocking. But a new kind of styling, on both the Duchess of Cambridge and the Duchess of Sussex, has pushed the short conversation into new territory: Dressy shorts, worn to work.
Meghan stepped out with Gloria Steinem in New York City last month in a pair of navy pleated shorts. (People magazine has a photograph.) Styled with an easy white button down and camel-colored belt, clutch, and heels, the daytime shorts were the standout piece in a relaxed ensemble. We know Meghan and Gloria have been working together again after the fall of Roe, which helps us interpret the duchess’s style choice. Could she have worn a dress? Absolutely, but that would have been a much different feel. I would have expected trousers for an obvious work-meeting look. Pleated shorts were a welcome twist, offering a professional vibe with a stylish, subversive bent.
Meghan leaving the Today Show in 2016. (Photo via Getty Images)
Related: I loved how Meghan’s look felt new but familiar. I’ve talked about this on Instagram (Kate’s navy and white polka dot Wimbledon dress is a great example); it’s the sign of a great visual brand. Meghan’s shorts were a nostalgic call-back to her pre-royal days, when some of her best looks were short suit ensembles. She’s been leaning into shorts since moving to California, too, spotted in several pairs at Harry’s polo matches (this black-and-white dressy ensemble was hands-down my favorite). She’s been paving the way with pleats as well. Remember those trousers she wore on the cover of Time magazine?
As for Kate, this week we saw her in her third pair of shorts in as many years. Each time she has worn shorts its been for a sailing engagement — we love a theme! But this pair was different. The duchess didn’t actually sail in her shorts as she had in the past; she changed into a wetsuit before climbing aboard the catamaran. Rather, Kate chose white Holland Cooper shorts for her arrival to her patronage, 1851 Trust, and for the engagement beforehand to discuss its sustainability efforts. These were not shorts for sports! They were shorts for work, the kind of work she would normally do in a dress or trousers. Her tucked-in navy-and-white Erdem sweater and bright white Superga sneakers made for a nautical vibe, but the shorts made the whole ensemble a bit more fun.
Kate arriving at a sailing engagement in Plymouth this week. (Photo via Getty Images)
Both duchesses looked fabulous in ensembles that were unexpected—and an unexpected look is guaranteed to garner more attention, which means more reach for their work. But what about the rest of us? Can we wear dressy shorts?
A Stylist Makes the Case for Shorts
I called up my friend Becky Malinsky, who just finished an impressive run at the Wall Street Journal as its deputy fashion director. She now is working as a personal stylist and brand strategist, helping advise clients on assembling a “stylish, functional wardrobe.” You can shop her recs in her great new newsletter, 5 Things You Should Buy.
Becky had a lot of fascinating thoughts on shorts, what message shorts send, and how to style them. Our conversation, below, has been edited and condensed for clarity.
Royals can wear dressy shorts. How about the rest of us?
Women who work in a professional workplace also have those unwritten fashion rules that lean very conservative and shorts, by definition, we just think of them in a more casual setting. So the idea of shorts just reads in our brain as inappropriate, but actually shorts can give you so much more coverage and can be so much more flattering and give you more mobility than a skirt.
Why do you think shorts are having such a moment?
Shorts are everywhere right now. I feel like it’s an extension of the suit. The suit has totally gone on its head. Offices are saying goodbye to the suit, but fashion is really embracing the suit.
We’re all coming out of COVID and everyone’s trying to reinvent themselves. People who wore suits all the time are looking at their closets and thinking: This all feels stale, it feels dusty. What’s a way that I can come into this new reality and feel dressed and polished, but with something new?
On the opposite end, people who love fashion are looking at a suit through a new lens, who maybe wore jeans and a cute sweater to work are looking at a suit as a really comfortable option that they can dress up. Maybe they will wear a cute striped T-shirt under a suit with a sandal, and it’s not [styled with] a button down and a pump.
So Many Thoughts is all about the message your style choices convey. What does a short say?
Confidence. You definitely give off a sense of confidence if you’re willing to take what we consider a fashion risk. A lot of us wouldn’t even think of shorts because our brain goes: Too casual or thinks of a denim cut-off.
A short that feels more dressed up and intentional can be an alternative to a dress. It’s a way to experience summer in a way that feels fresh right now, because it’s been about the dress for so many seasons. Shorts feel more interesting.
The style of short that Kate and Meghan are wearing, and that I bought for my summer meetings, they’re very polished, very unfussy. A short like that says: I’m willing to take a risk, but I still feel very in charge of myself and my situation.
There’s a vibe to shorts. What is it?
Shorts, and especially pleated shorts, really help balance the masculine/feminine energy. For me personally, and I think a lot of fashion people, balancing that masculine/feminine is where you find the sweet spot of an outfit. It helps your outfit fit into a lot of different situations. You’re not getting too dressy and too girly, but you’re also not so tomboyish that you don’t feel like yourself or don’t feel feminine.
Part of what I’m doing right now is working with a lot of executive women on their wardrobes. And the idea of being a powerful, confident woman does not just mean putting on a men’s suit. It means finding your femininity, but still feeling put together and polished. So it’s like taking a little bit of menswear elements, but still feeling very feminine, and still in control of your womanhood.
Ooh, yes. I feel like that sums up Meghan’s shorts look for her lunch with Gloria Steinem.
Makes so much sense for that occasion, too. But it’s also like for her, New York in the summer is 100% humidity and 95 degrees. It’s a way to participate in summer but still feel dressed.
Where should we start when shopping for shorts?
A short with pleats is actually a lot more flattering. It gives you the space to tuck in a shirt. It gives you the space to have a bit of fluidity while you move. Instead of it pulling while you’re walking, it just will still lay flat while you move.
I always size up in a short because I think a tight short is just not going to be flattering. Don’t be scared of the size on the label, really go with what feels good and roomy and you can move in, because it will be more flattering a bit looser.
Pleats do the same thing as sizing up. A pleat allows you to wear your size and still have that nipped waist, but have that more voluminous look.
What shorts are you loving?
I have been wearing a pair of khaki linen Bermuda shorts from Officine Générale all summer. I’ve been wearing them to take work meetings for lunch and with a little T-shirt to play with my two year old. The shorts dress up very easily in the same way I think a skirt would, but they give me more range. I’m not worried about going on the subway and sitting down on a seat because they’re a little bit longer.
How should we be thinking about wearing shorts or styling them?
It’s really helpful to tuck things in. It helps to see some waist.
To find that masculine/feminine energy, try a feminine piece on top to balance the menswear element on the bottom. If you want to wear a button down and have it untucked, I would say put a little camisole under it and wear the button down totally unbuttoned, almost like a little jacket.
For shoes, I like it when you can see some ankle. Try a ballet flat or a sandal, nothing that feels too sporty, again, bringing back that femininity. I think if you wanted to wear a sneaker, maybe a really plain white Keds or Vans, but nothing chunky or too trendy. The short is your trend moment. I really don't like competing trends. Pick a trend! If the trend is the shorts, keep everything else simple.
Thank you, Becky! You can find her on Instagram at @Becky_Malinsky.
Short Suggestions
Have we convinced you? I had to convince myself, so I faced my fears at the mall and a few more stores. Of the shorts I tried on at seven (!) spots, here are the four pairs I bought:
Click to shop: DRESSY. This pinstripe pair is the longest and dressiest I found, most like what Meghan wore. The built-in belt is great but can also be swapped out. Planning to wear these out to dinner with a white tank and flat sandals.
Click to shop: LINEN. Racks are filled with easy, elastic waist shorts right now but most looked quite casual to my eye. These, however, in black and white had great day-to-night potential, especially with a coordinating black or white blouse and gold jewelry.
Click to shop: PLEATED. If you buy one pair of shorts, buy these. MY FAVES (and half off right now!). The pleats and volume are as big as I am willing to go at the moment. Plus, they are longer without being long, if that makes sense. And so comfortable. A win!
Click to shop: FLAT FRONT. I know pleats might be a step too far for some and I respect that! Instead, try this higher-waist classic flat front pair in a color that will take you straight into fall. Channel Kate and tuck in your striped sweater. Plus, an elastic bit on the back keeps it comfortable.
Sizing guidance: Keeping Becky’s tip of looser-is-better in mind, I took multiple sizes into the fitting room. However, in the four I bought, I ended up going with my usual size (and, in some case, resisted the urge to size down). They are roomier by design — YAY.
Also, I was very drawn to simple ribbed tank like this striped one or this solid one to pair with all of these shorts. I bought both!
Note: I use affiliate links, which means that if you make a purchase I may get a small commission at no cost to you. Thank you for supporting my work.
Princess Diana at Walt Disney World in 1993. (Photo via Bob Pearson / AFP / Getty Images)
I will leave you now with this photograph of Princess Diana, proving everything we are trying to do she did first. 😉
Have a wonderful weekend, friends.
The So Many Thoughts Newsletter comes out twice a week. You can subscribe and catch up on the archives here, including:
➡️ What Everyone In London Was Wearing
➡️ Thoughts on the New Cambridge Portrait from an Art Historian
➡️ My Interview with the Downton Abbey Costume Designer
💭 Have Thoughts to share? I’d love to hear them! Hit “Join the Discussion” and leave a comment on my Bulletin page. You can also send me an email at Hello@SoManyThoughts.com.
Ok wait! Had to sneak this one in here, too. Are those pleats on young Will? An elastic waist on the little Harry? (Photo via Getty Images)