Tuck at least one side
A full tuck can feel too formal for a genuinely relaxed shirt like the Relaxed Fit Button-Down Shirt - but leaving it completely untucked reads shapeless. The middle ground: a loose front tuck, or tucking just one side in. It takes ten seconds and instantly creates a waistline the shirt doesn't have on its own.
Roll the sleeves, always
An oversized shirt with sleeves rolled to just below the elbow looks intentional. The same shirt with sleeves hanging past your wrists looks borrowed from someone taller. This is the single fastest fix if you only do one thing on this list.
Anchor the bottom half
Pair a roomy top with something fitted on the bottom — straight-leg trousers, a slim skirt, even well-fitted jeans. The Relaxed Denim Shirt over the High-Waisted Straight-Leg Trousers works because the volume is only happening in one place at a time, not two.
Let the fabric hold the shape
Cheap oversized shirts collapse into a shapeless bag by hour three. Cotton poplin doesn't - it's crisp enough to hold its own structure even loose, which is most of why an oversized shirt looks styled instead of slept-in.
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