If you carry an umbrella, it won't rain, and if you don't, it will. You want an umbrella that won't collapse or invert in the wind. The grip must be comfortable throughout your walk. Stick umbrellas are harder to carry rolled up but usually have bigger canopies and better grips. Compact umbrellas store well but often have a tiny, uncomfortable grips and small, shallow canopies.
1. ShedRain Pro-Reflect Jumbo Sports Umbrella
Reflective trim around the edges makes this a great choice for walking in foul weather and at night. The rubber handle is gooved for a good grip. You can take it along easily with the carrying strap to wear it over your shoulder until needed. It opens to 58 inches for good coverage.
2. ShedRain Windpro Umbrella
Wind tested to 33 mph. This 46" arc umbrella resists inversion. It is 18 inches long when folded.3. Swiss Army Automatic Umbrella
Sorry, it doesn't have a scissors, toothpick, or even a pocket knife. But Victorinox makes high-quality items, and this umbrella is no exception. It's a compact 13 inches until it automatically unfurls in 3 stages. It has a wind-reflex frame to prevent inversion and made with a titanium alloy for strength. The grip is a comfortable TPR-molded handle.4. ShedRain Windjammer Jumbo Umbrella
Big 58" arc to keep you dry, but compacts to 22 inches. Comfortable 3-fingered wood grip with leather strap. The vented cover is designed to resist inversion in the wind.5. Gellas Gel-Handle Mini Umbrella
This umbrella has a gel-filled handle to fight handle fatigue. A compact umbrella to carry along, only 9 inches long when closed, opens to a 43 inch arc.6. Gustbuster Metro Style Umbrella
Windproof and waterproof with a 43 inch canopy and a larger handle for comfort.7. Samsonite Ultra Mini Flat Umbrella
My walking friends say the surest way to prevent rain is to carry along an umbrella. These models are very packable, between 6 and 8 inches long folded. The drawback is the tiny knob when you unfurl them, which can be uncomfortable after any time. That said, these are my favorites as they are easy to stow away or carry easily like a baton once the shower is over.