Effortless shirts you’ll love for workdays, weekends and beyond
From crisp cotton classics to relaxed silhouettes, these shirts strike the perfect balance between structure and ease.
By Arielle Katos
FEW FASHION pieces evoke effortless polish quite like the oversized shirt — arguably one of the most perennially stylish staples in a woman’s wardrobe. While the crisp, tailored silhouette remains a classic, in 2025 it’s the more relaxed, loosely structured iterations that feel undeniably modern. They carry a quiet confidence — a sense of ease that says, I’m comfortable — without ever compromising on style.
Moreover, fashion historians may recall that the cotton shirt first rose to prominence when Marie Antoinette famously wore what was then considered a night garment in a painted portrait — a scandalous choice at the time. Since that moment, the silhouette has evolved significantly. Today, the shirt is beloved by contemporary designers and A-listers alike for its versatility, ease, and quiet sense of rebellion. Case in point: Miley Cyrus (pictured above), Kaia Gerber and Elizabeth Debicki (below).
Endlessly versatile, the oversized shirt is a modern wardrobe staple. Here are our favourite styles to wear now.
The best women’s oversized shirts
1
Matteau
Blue Classic Stripe Shirt
1
MATTEAU
Matteau Blue Classic Stripe Shirt
$605
This classic oversized style is made from BCI-certified cotton.
2
Maison Margiela
Blue & White Stripe Cotton Shirt
2
Maison Margiela
Maison Margiela Blue & White Stripe Cotton Shirt
$1545
A high-end shirt from Maison Margiela that will be in your wardrobe for years to come.
3
VIKTORIA + WOODS Gospel Shirt
3
VIKTORIA + WOODS
VIKTORIA + WOODS Gospel Shirt
$390
The Gospel Shirt is a versatile staple with a refined design, paired with a matching halter bralette, effortlessly transitioning from work to weekend.
4
COS Oversized Tailored Shirt
4
COS
COS Oversized Tailored Shirt
$125
The sharp collar and cuffed long sleeves give this budget-friendly COS piece a refined, tailored edge.
5
BLANCA Opal Shirt
5
BLANCA
BLANCA Opal Shirt
$280
Featuring bold vertical stripes in a deep, sophisticated hue, this Blanca oversized button-up exudes relaxed refinement.
6
CAMILLA AND MARC Novella Boxy Shirt
6
CAMILLA AND MARC
CAMILLA AND MARC Novella Boxy Shirt
$450
The Novella Boxy shirt combines classic elements with thoughtful details, perfect for everyday wear.
