Certainly, here are some options for outerwear and other clothing items that may be suitable for walking around a mildly windy city in light to medium rain:

Rain Jacket - A good quality rain jacket is a must-have item for walking around in the rain. Look for jackets that are made of waterproof and breathable materials like Gore-Tex, which will help to keep you dry and comfortable. While the cost of a good rain jacket can vary, you can typically find one that fits your budget. A rain jacket should keep you relatively dry, but it's important to note that some may not offer full coverage, so you may still get wet in areas not covered by the jacket.

Waterproof Poncho - A waterproof poncho is an alternative to a rain jacket and can be a great option for those who prefer more ventilation while walking. They are often made from lightweight and waterproof materials and can be less expensive than a rain jacket. However, ponchos may not provide as much coverage as a jacket, so you may still get wet in certain areas.

Rain Pants - If you're walking a longer distance in the rain, consider wearing rain pants as well. They are made from waterproof materials and will help to keep your legs dry. However, they may not be as breathable as regular pants, so it's important to find a pair that offers good ventilation.

Waterproof Boots - Waterproof boots are a must-have when walking in the rain. They will help to keep your feet dry and comfortable, and they can also provide good traction on wet surfaces. While they can be more expensive than regular boots, they are a worthwhile investment for those who frequently walk in the rain.

Umbrella - A good quality umbrella can be a great option for those who prefer not to wear rain gear. However, it's important to note that umbrellas are not always practical in windy conditions, and they may not offer full coverage in heavy rain.

In terms of comfort, rain jackets, ponchos, rain pants, and waterproof boots can all be comfortable options, provided that you find the right fit and material. Breathability is also an important factor to consider, especially if you're walking a longer distance. Look for materials like Gore-Tex or other breathable fabrics to ensure that you stay comfortable and dry.

As for cost, these items can range from affordable to expensive, depending on the brand and quality. However, investing in good quality rain gear can be a worthwhile investment if you frequently walk in the rain.

Finally, if you're walking about a mile to work in light to medium rain, any of these options should keep you relatively dry. However, keep in mind that heavier rain or longer distances may require additional gear or adjustments to your clothing to ensure your comfort and protection.
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