Yara: How do I wear High-Waisted Jeans? A: This season everyone want to Channel their inner Modern Katherine Hepburn with the high-waisted trend. It’s all about proportions daaahling. it's actually very flattering to wear wide high-waisted pants to make the most of an hourglass figure. Just make sure to tuck a fitted t-shirt and a vest or a fitted romantic top (with frills if you like) to balance the look. If you feel it’s too cold outside, then complete the look with a cropped swing jacket or a capelet and high heeled patent platforms. If you want to try the skinny high-waist look, then expect a lot of green envy from your peers and mall on-lookers as it’s tough to pull off this style and you need the have right curves honey (but not too much of them). Pair the skinny high-waisted jeans or pants with a loose tucked top and flats. Wear suspenders if you want to look daring. How would you wear your high-waisted pants/skirts?