An anchored stand—that is, a stand that is attached directly to the ground or deck—holds up best in windy conditions. However, this type of stand isn’t always practical, so freestanding stands are appropriate too, as long as they’re heavy and large enough. Many manufacturers will recommend a stand weight for their umbrellas (and most sell their own version to match). You can go up in weight if you’re concerned about your umbrella staying put in windy conditions.