A striped oversized t-shirt might seem like a casual staple best reserved for lazy weekends — but with the right styling, it can easily transition into a sleek evening ensemble. Start by choosing a well-fitted pair of high-waisted black skinny jeans or structured leather pants. The contrast between the oversized silhouette and jogging stone island contoured pants creates a flattering proportion that’s both trend-forward.

If you want to add a bit of edge, opt for glossy patent trousers for a modern, rebellious twist. Layering is key. Throw on a tailored moto jacket or a denim shacket. A beige wool blazer adds sophistication and polish, while a denim jacket keeps things unfussy and stylish. Make sure the jacket hits just above or at the hip to create definition and avoid a shapeless silhouette.

Footwear can make or break the look. Chunky combat boots will instantly elevate the outfit. athletic shoes should be avoided unless you’re going for a urban street-style aesthetic. Heeled sandals with a minimalist design also work beautifully during warmer months.

Accessories should be intentional. A focal accessory like a oversized pendant or hoop earrings or a minimalist timepiece will draw attention without overwhelming the striped pattern. Carry a structured clutch in a monochrome hue like navy or burgundy that complements the look without competing with the stripes. Don’t forget to add a deep berry gloss or a subtle sculpting to bring focus to your face and complete the transformation.

Finally, pay attention to fit and proportion. If your t-shirt is extremely loose, consider creating a front knot to define your shape. Avoid bulky layers so the outfit doesn’t feel cluttered. The goal is to look put together without trying too hard. Stripes are timeless, and when styled thoughtfully, an oversized tee becomes a fashion-forward anchor for any evening out.