6 Worst-Dressed Celebs at the 2026 Emmys: From Shailene Woodley to Bill Posley

Forget the outfit for a second. Can we just talk about the hairstyle? The mohawk with purple highlights had us checking our calendar to make sure it wasn’t still the 2019 TikTok era. Sigh, it is not. So, no idea why Bill Posley is sporting the hairstyle then. Now, focusing on the attire, Posley walked the red carpet in a purple kilt paired with ombré tights. The shoes, the outfit, the hairstyle... none of it seems to make much sense together. If he was going for a Highland-inspired look, he should have gone all in with a sporran, jacket, and waistcoat. Then maybe, just maybe, the whole look could have been saved.

Joanna Calo wore a sky-blue dress featuring a bubble silhouette. While the outfit wasn’t particularly bizarre, it still made our worst-dressed list because of the lack of harmony between the top and the skirt. The voluminous skirt just doesn’t seem to work with the sleeveless top. An A-line skirt might have worked better, but it probably would have made the whole look forgettable. At least this one is standing out, though not for all the right reasons.

We just have one question for Shailene Woodley: Why? Everything, from the plunging periwinkle top to the beaded gold pants, burgundy opera gloves, and gemstone Howl Jewelry necklace, was clashing. There was just way too much going on. We love Woodley, but this outfit is a nightmare. Why in the world would anyone want to go for such an unflattering look? All that creativity, and for what? Nothing about this outfit works together.

No! That’s what Jean Smart should have said when she was offered this boring attire for the Emmys. Smart donned a black, floor-length gown featuring metallic silver pleated sleeves and a V-neck bodice. But we’re pretty sure we’ve seen the exact same, or at least a very similar, dress worn by many celebrities in the past. It’s the Emmys! The dresses celebrities wear should be unique, creative, and different, not something that looks like it has been repeated on the red carpet time and time again. Yawn. Next!

Meg Stalter chose to dress for the Emmys as... Emmy. She wore a metallic gold two-piece set featuring a bra top and hot pants, paired with a chunky gold belt and golden sandal heels. Stalter even covered her entire body and hair in gold paint. Talk about commitment! To fully mimic the trophy, she had sculptural wings attached to her back and carried a large golden sphere representing the trophy’s atomic globe. It’s not the worst look, per se, but the choice of dress was certainly a little questionable. Still, that’s one bold outfit, and we’ll give her that.

Lisa Ann Walter stepped out in a head-to-toe black dress on the Emmys red carpet, and the gown was giving spooky vibes. It would have been perfect for a Halloween party, but the Emmys? Not quite the place for it. The strapless mermaid-style gown featured form-fitting ruching running down the length of the bodice, which looked fine... until you noticed the detached sheer tulle mesh sleeves. What was going on there? The whole thing felt like maximalism gone wrong.