067: 1 Shirt, 4 Ways
My commitment (finally) to a plaid shirt
Plaid shirts and I have had a historically anxious-avoidant relationship.
The plaid shirt’s anxious attachment manifests in the item flooding my Pinterest boards, catching my eye on various outfits, and stopping me mid-scroll as I online shop. However, the closer I get to committing to one, the more I pull back—afraid of what it means to incorporate it into my wardrobe.
My chronic fear of colour and pattern has led to this push-and-pull dynamic. Neutral colourways or non-patterned items allow me to uphold my getting-dressed philosophy: effortless yet chic. I subconsciously know that each neutral or non-patterned item will complement the other, forming a cohesive outfit. When it comes to colour or print—plaid print in this case—that ease doesn’t apply as easily. Suddenly, the shade of green in your plaid shirt must be intentionally paired with the right blue in your trousers, or the khaki of your jacket has to complement the firetruck red stripes in the shirt. This added layer of thinking directly opposes the ease I strive for when getting dressed, leaving me to love plaid shirts from afar.
However, this summer, I’ve committed to exploring the items that have historically scared me—and finding ways to make them my own. Which brings me to my purchase: a plaid shirt from Massimo Dutti.
I opted for a men’s shirt because I wanted it to feel roomy without being overly oversized. Women’s shirts can often be too slim-fitting, which introduces a crispness I don’t love. I like my tailored or classic pieces to still feel relaxed and casual. A men’s shirt gave me that slouchy, undone feel while maintaining the classic structure of a button-up.
Now, you could say the print is a cop-out—but I’d argue it’s me staying true to myself while still stepping out of my comfort zone. The beige shirt, with its slightly darker plaid pattern, allowed me to make my foray into plaid territory without the print feeling too bold or intimidating. It has the same effect as a traditional plaid shirt, but with the volume dialled slightly lower—making it easier to style in a way that still feels effortless.
As soon as it arrived, I began exploring ways to make it work seamlessly with the rest of my wardrobe. Here are four outfits I styled featuring my new shirt:
For this outfit, I wanted a lunch look that felt equal parts sophisticated and cool. A recent addition to my wardrobe is this butter yellow skirt from Cos—a chameleon piece that works from day to night. At first, the shirt felt frumpy when draped over the skirt, with both pieces falling straight down and lacking shape. I introduced a silhouette by adding a skinny belt from Cos to cinch the waist slightly, creating a more flattering structure.
Once that was in place, the rest came together seamlessly. The Manolo slingback pumps, in a neutral tone, complement both the beige shirt and butter yellow skirt, and the cap added a necessary pop of colour to complete the look.
Pairing the shirt with my Citizens of Humanity Ayla jeans—a most-worn and well-loved item—was a no-brainer. But I wanted to take it from expected to exciting. I tied a red bandana across my waist, which added a pop of colour and acted as a visual break between the pieces while maintaining cohesion. I echoed the red with my Bottega Veneta pumps in a red croc pattern.
For sunglasses, I reached for my Julia Roberts in My Best Friend’s Wedding-esque pair: the Keppe Sun from Moscot. They give me that rockstar edge, and alongside the bandana, brought an extra attitude to the look.
This is my favourite look in the newsletter. It most closely captures my personal style—tailored yet relaxed, with a touch of cool. I started with these new barrel-leg trousers from Arket, a summer purchase that feels polished but breathable for 20-degree-plus days. Made from 100% lightweight cotton, their structured shape gives intentionality without effort.
When paired with the shirt, the outfit looked smart, almost too smart. So I introduced friction by adding Havaianas and a red New Era cap. The contrast grounded the look and gave it that easy, unfussy energy I’m always chasing.
Shorts and a shirt, not groundbreaking, but with intention behind each silhouette, the look becomes more refined. The loose fit of the shorts, combined with the relaxed shape of the shirt, makes the outfit feel casual yet considered.
To sharpen the overall look, I added my Aeyde pumps—another beige-toned item that plays nicely with the shirt’s pattern and elevates the outfit just enough. The chunky Madewell belt breaks up the shirt and shorts, while acting like a piece of jewellery. A final injection of colour came through my Jil Sander bag, which felt like the perfect punctuation mark for the look.
This experiment with plaid has taught me something I already knew deep down but often forget: personal style is less about fixed rules and more about finding your own rhythm within them. The goal isn’t to eliminate friction altogether—but to learn how to work with it, to use it as a tool that brings dimension and intentionality to your wardrobe.
By choosing a version of plaid that felt approachable to me, and styling it in ways that honour both ease and elegance, I’ve taken a once-intimidating item and made it feel like mine. I’m learning that stepping outside of your comfort zone doesn’t have to mean abandoning yourself—it can mean expanding your definition of what suits you.
Wardrobe Therapy: Explore Your Style from the Inside Out
If you resonated with this exploration of hesitation, curiosity, and finally finding alignment in your style, Wardrobe Therapy might be exactly what you need. It's a 3-session offering designed to help you unpack the why behind your wardrobe choices, understand your personal style more deeply, and rebuild your wardrobe to reflect who you’re becoming.
Together, we’ll explore the pieces you avoid, the ones you’re drawn to but never buy, and the quiet instincts you often override. Whether you're in a style rut or standing at the edge of change, Wardrobe Therapy is a space to reconnect—with your clothes and yourself.
✨ Click here to learn more and book your sessions
(Or reply to this newsletter with any questions—I’d love to hear from you.)Let’s make your wardrobe feel like home.
I may earn some commission if you make a purchase using the links above. Happy shopping!
You can find all the links featured in the newsletter on my ShopMy here.
For all in real time outfits, follow me on Instagram here.
I looove all of these looks, but beyond that, I love reading your thoughts on personal style. This one particularly resonated: "personal style is less about fixed rules and more about finding your own rhythm within them." So good! x
I love every look! #2 and #3 are in my screenshots to recreate. So chic.