Q: How do you wear a collared shirt with rolled up sleeves underneath a sweater?
A: Rolling up your dress shirt sleeves under a sweater and having it look good requires that you don't actually roll them up. The formula is: scrunch, flip, flip, scooch. Now this may sound like a Dr. Seuss Kabuki dance but it's quite simple.
Step 1 - With your shirt sleeves all the way down, put on your sweater and gently scrunch up the sweater sleeve until it's at your mid forearm.
Step 2 - Flip the cuff over twice so the exterior of the cuff is neatly tucked into itself like the image below.
Step 3 - Scooch the sleeve gently up your arm so the sweater sleeve rests fully inside your doubled up cuff.
The best proportional placement of the rolled cuff is at the mid forearm and up to directly above the elbow.