As every Silicon Valley titan surely knows, assembling a holiday party wardrobe that works across occasions—perhaps time zones, too—requires considerable strategic thinking: Underperformance isn't an option, and neither is cutting deeply against the cultural grain.

Thankfully, stylist Victoria Cárdenas Hitchcock has a bunch of shortcuts for getting it right. To start, "men should look for classic-meets-modern pieces that travel well," said Cárdenas Hitchcock, who is known for a low-profile, high-luxury aesthetic embraced by heavyweights at Uber, Google and Apple. "Don't rely on big labels to look good either. Clothes are an extension of your personal brand and should feel authentic to you."

For the guide below, I turned to other sartorial consiglieres to the tech set, like Emily Holt, a former Vogue editor and owner of the very chic Hero Shop in San Francisco. Holt provides a tight designer curation aimed at women founders and executives, and when we spoke, she was particularly enthusiastic about the embellished blazer trend that appeared everywhere on the fall runways. "A little sparkle on a familiar piece is reassuring—it signals a party mood, but you're still in your comfort zone," she explained. Of course, the trick is understanding how much to wear. "If your jacket has major sparkle, tone it down with a simple skirt or pants," Holt said. "Less is more."