Oversized shirts have completely transformed our approach to casual dressing, and we’re genuinely thrilled by how they make it possible to look stylish and intentional while feeling like you’re wearing the most comfortable pajamas imaginable. There’s something so perfectly effortless about the oversized silhouette—it creates these beautiful, flowing lines that are incredibly flattering while being forgiving enough that you can actually move, breathe, and live comfortably throughout your day. We’ve been living in them for work-from-home days, lazy weekend mornings, casual errands, and basically any time when comfort is the priority but looking good still matters. The key to styling oversized shirts is playing with proportions—we love them tucked into high-waisted bottoms for shape, tied at the waist for a more fitted silhouette, or worn completely loose with fitted bottoms for that perfect balanced contrast. They work beautifully for layering too, worn open over fitted tank tops, under cardigans and blazers, or even tied around the waist as improvised jackets when the weather changes unexpectedly. The relaxed fit also makes them incredibly versatile for different body types and comfort levels—they never feel restrictive or uncomfortable, but somehow still look polished and deliberate when styled thoughtfully. We’ve discovered they’re perfect for travel, casual dates, and those transitional moments between seasons when you need something substantial but not heavy. They’re basically the uniform of people who want to look good without sacrificing comfort.
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Bottega Veneta Embroidered Cotton Oversize Shirt
Original price was: $870.00.$529.00Current price is: $529.00. -
Etro Multicolor Striped Cotton Paneled Oversized Shirt M
Original price was: $194.00.$174.00Current price is: $174.00. -
KEFITEVD Women’s Button Down Blouses Casual Oversized Shirt Blue,M
Original price was: $33.46.$2.71Current price is: $2.71. -
MAISON KITSUNE PARIS EMBROIDERY OVERSIZE TEE-SHIRT Size: L, colour: BL
Original price was: $95.00.$62.00Current price is: $62.00. -
MAISON KITSUNE PARIS EMBROIDERY OVERSIZE TEE-SHIRT Size: M, colour: WH
Original price was: $95.00.$62.00Current price is: $62.00. -
Max Mara Multicolor Tropical Print Diego Oversized Shirt Dress L
Original price was: $231.00.$208.00Current price is: $208.00. -
Maxi Dress White Turndown Collar Long Sleeves Oversized Shirt Dress
Original price was: $36.34.$27.26Current price is: $27.26. -
Pink Plaid Printed Shirt Oversized Spring Tops For Women 2025
Original price was: $27.56.$17.91Current price is: $17.91. -
QUIRA Oversized shirt
Original price was: $855.00.$428.00Current price is: $428.00. -
Santiago Womens Oversized Shirt – Green
Original price was: $49.99.$29.99Current price is: $29.99. -
Shirt Calvin Klein Jeans Oversized Long Sleeve Denim Shirt Denim S
Original price was: $82.95.$58.49Current price is: $58.49. -
Shirt Calvin Klein Jeans Oversized Longsleeve Denim Shirt Denim XS
Original price was: $82.95.$62.49Current price is: $62.49. -
Sisley – Green Striped Oversized Shirt, Woman, Green, Size: XS
Original price was: $59.95.$41.96Current price is: $41.96. -
SPORTY & RICH SRC logo oversized shirt
Original price was: $235.00.$141.00Current price is: $141.00. -
Victoria Beckham Multicolor/Cream Textured Crepe Oversized Shirt XS
Original price was: $194.00.$174.00Current price is: $174.00.