6 Things You Should Never Wear with Heels

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We might be devoted sneaker enthusiasts and overall fans of flats (aren’t we all?), but no one can deny the allure of a great pair of heels. That is, as long as they’re worn the right way. (There’s a time and place for four-inch leopard pumps.) Here, six heel-outfit combinations to avoid at all costs.  

1. Jean shorts with stilettos. We know—your legs are the stars of the show here. But a classier way to flaunt them off is with demure flat sandals or low-profile sneakers. If you must add a little height, do so with beachy wedges and a loose-fitting top.

2. A miniskirt with platform pumps. First, short skirts tend to fit snug (to stay in place). When you add six inches of pumped-up calves and the silently obvious risk of rolling an ankle, you’ve officially veered into tacky territory. Next time, check out our go-to guide for pairing hemlines with heel heights.

3. Flared pants with peep-toes. Wide leg openings with heels can be majorly leg-lengthening, but it all depends on extending the line. Strappy wedges and flatform sandals work best because they have a similar weight to the hemline. A delicate peep-toe, however, fans you a little too close to the 2002 Dirrty-era Christina Aguilera flame.

4. Leggings or sweatpants with any heels. If your bottoms say “gym,” your shoes shouldn’t say “club.” Yes, the first wave of athleisure tried…so hard…to make this combo work, but alas. 

5. Summery sandals with a pencil skirt. Again, it’s about matching the vibe of your outfit to the vibe of your shoes. Business professional and lobster bake aren’t exactly the same.

6. Anything you can’t walk in. You know, unless “newborn baby calf” is the look you’re going for. (Don’t believe us? Google “runway fail.”)

RELATED: 12 Pairs of Spring Sandals, All Under $200

sarah stiefvater

Wellness Director

Sarah Stiefvater is PureWow's Wellness Director. She's been at PureWow for ten years, and in that time has written and edited stories across all categories, but currently focuses...