A well-made, slightly boxy and oversized shirt is proving to be a fashion winner this season.
What’s that you say? They’re a winner every season? Too right.
It’s why if you choose judiciously right now, a great piece will likely stick around in your wardrobe for many seasons to come.
But how do you choose with longevity in mind?
We’re particularly enamoured with the considered details of the shirts Kiwi designer Lucy Maxwell has always included in her label Josephine, first launched in 2023. This season’s star is Josephine’s Cropped Viv shirt, a classic blue style with slight tweaks, like oversized cuffs, that give it a fresh, desirable feel.
“What I love about a cotton shirt is the ease of it,” Maxwell says. A good shirt has enough structure to feel polished, but it can still be worn in a way that feels relaxed and completely your own. I also love how much you can do with proportion, which is something I always come back to in my own styling.”
She also believes the best shirts have a life beyond one particular way of styling them. “If you can only wear it one way, or only for one type of occasion, it’s probably not doing enough for your wardrobe,” the designer says.
“I’m always looking for that versatility, a piece that feels completely right at 9am but doesn’t look out of place at 7pm.”

She says it’s the little things that make a difference when choosing something you’ll love to wear, but they can also let a design down.
“Poor fabric choice, an awkward collar or cuffs, or proportions that don’t quite work can completely change how a shirt feels on the body.”
She says she’s always paid a lot of attention to detail in her designs and that construction and finishing are important. “You can tell when the details haven’t been considered, particularly in the way a shirt sits, moves and holds its shape after wearing.”
Those larger cuffs in her shirts have become something of a signature. “I love how they look rolled up and the way they change the proportion of the sleeve. I also wanted the inside of the shirt to be considered and just as beautiful as the outer garment, as it is with all our pieces, which is why I used white internal facings. It’s a small detail, but one that becomes visible when the shirt is worn open, or the sleeves are rolled.”
For the new season she will be wearing her shirt unbuttoned with her label’s relaxed wide-leg Mika Pants, layered over a tank or T-shirt and finished with her favourite sandals.
“I also love it with the Gracie Maxi Skirt, buttoned up with a little half tuck,” she considers. “It feels like the perfect spring look and shows how differently you can wear the same shirt.”


