However turbulent 2020 has been, one thing is constant: Japan’s rainy season. As workers creep out of their homes, onto trains and into their offices, bracing the weather all the while, heels or regular loafers may not cut it. What you really need is comfortable, water-resistant footwear that also looks good.

Luckily, Japanese shoe retailers have lived through the rainy season long enough to offer us a variety of water-wicking renditions of timeless shapes, from Chelsea boots to Mary Janes to sneakers, from elegant and polished to stylishly sporty. Here are our top choices for the season. 

1. The Suit Company Side Gore Boots

You need not sacrifice professionalism for functionalism, even when you’re bracing the wet weather on your commute to work. Sporting these side gores, you can get away with wearing rain boots in the workplace. Plus, these have a pointed toe, elongating the legs and giving a delicate flair to an otherwise plain professional getup. While the top of the shoe is made of PVC resin, ensuring flexibility and no wear, the sole is a type of rubber ceramic to prevent slippage. Pair these with slacks and do away with stuffy work shoes. Buy at all The Suit Company stores in Japan or online. ¥9,800

2. Blundstone Side Gore Boots 

Contrary to popular belief, Chelsea boots are not just winter wear. In fact, the fitted shoe is perfect for blocking moisture and walking long distances in the mucky heat, not to mention their slim, neutral shape goes with anything from slacks to shorts to skirts. While long, oversized pants create a laid-back look, pair these boots with colorful socks and knee-length shorts for a playful and preppy feel. Blundstone’s water-resistant leather prevents water ingress from the top of the shoe to the sole, and the cushioned heel allows for comfortable walking with reduced shock to the hips and feet. Buy at Beams stores in Japan or online. ¥25,300

3. Adidas Advantage Base Shoes

Love summer but hate dressing for the rain? These sleek sneakers, sporting the three Adidas stripes in the form of perforations, are ever practical (with a synthetic leather body) while maintaining the sporty and stylish integrity of your upper half. With various tongue, sole and upper colors, you can adapt this time-honored shape to the occasion – without worrying about the weather. Buy at Adidas and other sportswear stores in Japan or online. ¥6,039

4. Moonstar All Weather Side Gore Boots 

This unique pair meets hypebeast and fisherman. Moonstar’s Fine Vulcanized series boasts soft, steadfast and finely-silhouetted shoes with a laminated rubber base that enhances waterproofing. Despite the rain boot vibe associated with rubber, the sleek shape of the side gores makes them perfect for the campsite and the concrete alike. Buy at Beams stores in Japan or online. ¥16,500

5. Nike Classic Cortez

Nike Cortezes were first released in 1972. Their timeless simplicity and durability have won them the title of shoe staple into present day. Not only are they endlessly versatile, whether in red/white/blue or sleek black and white, but they are also waterproof. They are also perfect for spring and summer. The low ankle and thin sole make for lightweight wear and a seamless look that can be casual or classy – and always comfortable. Buy at Nike or ABC Mart stores in Japan or online. ¥11,000

6. Converse All Star Light

Sometimes, we’re not willing to give up our Converse for a day – or a month – of rain. The solution: the rainy-season rendition of the classic All Star high-tops, complete with an EVA outsole (to prevent slipping), a urethane insole (for breathability and cushioning), a gusseted tongue (to keep out water) and the star logo that we love so much. These are essentially rain boots in disguise. Buy at ABC mart and other footwear stores in Japan or online. ¥8,800

7. Joli Encore Platform Sidegoa Boots 

Wistfully longing for fall as you try to ignore the humidity? These wine-colored gore boots are distinctly autumnal and give a gothic edge to a lighter summer getup. At the same time, they’re perfect rain shoes, easy to slip on and, with the chunky platform sole, endlessly comfortable and supportive. But at ABC Mart stores in Japan or online. ¥2,739

8. Hunter Penny Loafer 

The classic rain boot brand doesn’t just offer clunky all-weather wear: this pair meets the clean and sleek look of a ladies’ loafer with the functionality of bigger boots. Offered in gray, sunrise and black, the playful lineup will add color to any office outfit. Plus, the natural rubber surface prevents too much abrasion (but may start to speckle or whiten with time). Buy at Ray Beams stores in Japan or online. ¥16,500

9. Moonstar T Stripe Leather Shoes 

This waterproof version of the Mary Jane can be paired with just about anything, from an ankle-length summer dress to a fitted pair of jeans. Some pattern socks give your getup a fashion-forward playfulness, while worn with translucent tights you’re ready for the workplace. The slight heel and thick sole only increase durability and resistance to rain, whether you’re wandering around the city or commuting to work. Buy at Beams stores in Japan or online. ¥22,000

10. Fox Umbrellas Ribbon Rain Loafers 

Bored with boots but terrified of flash rain? Long-lasting and deceivingly sleek, these loafers might be for you. They are airy, chic and, with their jagged sole, slip-proof. Fox Umbrellas is known for manufacturing rain goods for the British royal family and Japanese imperial family. The practicality, elegance and quality central to their brand runs through this pair, while the ribbon detail elevates the classic shape. Buy at United Arrow stores in Japan or online. ¥13,200