If you're looking for the best outerwear and other options for walking around a mildly windy city in light to medium rain, you might want to consider the following factors: comfort, breathability, cost, and how wet you'll be after walking about a mile to work. Here are some possible choices and their pros and cons:

- A waterproof jacket: This is a classic option that can keep you dry and warm in rainy weather. A waterproof jacket usually has a hood, a zipper, and some pockets to store your essentials. Some jackets also have vents or mesh lining to improve breathability and prevent overheating. However, a waterproof jacket can also be bulky, heavy, and expensive. Depending on the quality and material of the jacket, it might not be very durable or easy to wash.

- A raincoat: A raincoat is similar to a waterproof jacket, but it is usually longer and covers more of your body. A raincoat can protect you from the wind and the rain, and it can also double as a fashion statement. Some raincoats have belts, buttons, or patterns that add some flair to your outfit. However, a raincoat can also be less breathable, more restrictive, and more prone to wrinkling than a waterproof jacket. It might also require more care and maintenance.

- An umbrella: An umbrella is a simple and versatile option that can shield you from the rain without adding any extra weight or layers to your body. An umbrella can also be folded and stored easily when not in use. You can choose from different sizes, colors, and designs of umbrellas to suit your preferences and personality. However, an umbrella can also be inconvenient, fragile, and ineffective in windy conditions. It might also get lost, stolen, or forgotten.

- A poncho: A poncho is a large piece of fabric that you can wear over your clothes like a cape. A poncho can cover most of your body and keep you dry in light to medium rain. A poncho can also be cheap, lightweight, and easy to pack. Some ponchos have hoods, sleeves, or pockets for extra convenience. However, a poncho can also be unflattering, uncomfortable, and noisy in windy weather. It might also tear easily or get tangled with your belongings.

- A hat: A hat is a simple accessory that can keep your head and hair dry in rainy weather. A hat can also protect you from the sun and add some style to your look. You can choose from different types of hats such as baseball caps, beanies, fedoras, or berets. However, a hat can also be insufficient, uncomfortable, or inappropriate for some occasions. It might also get blown away by the wind or ruin your hairstyle.
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