Jeri Ryan Attends Dream Halloween Benefit in Santa Monica, 2000 • CelebMafia

With red boots, a leather coat, and a hint of gothic glam, Jeri Ryan brought moody elegance to the pumpkin-lit carpet at the Seventh Annual Dream Halloween.

Halloween events tend to invite excess—costumes, camp, and chaos. But Jeri Ryan, ever the style tactician, chose a different route at the Seventh Annual Dream Halloween Benefit in Santa Monica on October 28, 2000. Her look? A brooding cocktail of fall textures, vampy accents, and just enough polish to keep it red carpet-ready.

Ryan wore a black dress layered under a black leather coat—structured, sleek, and seasonally spot-on. The dress itself was simple but effective: short enough to show off her boots, fitted enough to hold its own beneath outerwear. The leather coat added edge, while the monochrome palette kept things cohesive and quietly dramatic.

The standout piece? Red knee-high boots—bold, glossy, and perfectly timed for a Halloween-themed event. They added a pop of color and a touch of theatricality without tipping into costume territory. Her black-and-red handbag echoed the boots’ palette, creating a visual throughline that felt intentional. A lanyard with an event badge hung around her neck, grounding the look in its charitable context.

In 2000, Halloween fashion was still finding its footing between kitsch and couture. Ryan’s look leaned into the latter, offering a template for how to do themed dressing without losing style credibility. It’s a move we now see echoed in modern celebrity photos —where even the most playful events demand sartorial strategy.

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