Warm-Weather Rain Essentials

Planning a stylish outfit with the rain in mind isn’t difficult if you are prepared with the essentials. Sometimes, the rain is so torrential that going outside requires more than grabbing an umbrella on your way out the door. I’ll never forget the time I attended a fashion forum at FIT. It rained continuously that day, but I was determined to arrive looking and feeling my best. I spent a great deal of time coming up with the perfect outfit for warm-weather downpours, and I’ve repeated it in a similar fashion over the years. This winning look is composed of rain boots, an A-line skirt and a complementary shirt, a lightweight jacket, and a rain-appropriate bag.

Rain Boots

Knee-high rain boots are perfect for a walk in the mud, but otherwise they can be heavy and uncomfortable to wear for an extended period of time. I’ve owned the same Hunter Chelsea-style rain boot for years, and they continue to meet my needs over and over again. My black, glossy style is similar to the boots included in look #1. I don’t feel the need to take them off when I get where I’m going; they’re versatile and extremely chic.


A cheaply made umbrella never did anyone any good. I am partial to London Undercover. I’ve owned the umbrella pictured in looks #1 and #3 since 2018. It has survived London rain and excessive Edinburgh winds. While I don’t recommend that you subject it to high winds, the fact that mine is still intact after being open in the elements of Scotland attests to its durability.

Lightweight Jacket

If you haven’t done so already, you must find a lightweight jacket suitable for warm-weather rain. I usually wear a trench coat on days like this. Since I am accustomed to carrying an umbrella, I don’t necessarily need to wear a waterproof jacket (unless the windspeed is high). I love the way the belts on coats of this style define my waist. Additionally, the traditional mid-thigh length always seems to be right.

A-line Skirt and Complementary Shirt

Think of how pleased you’ll be when you arrive at your destination in your dry outfit. I usually wear a skirt when it rains because I’d rather not walk around with wet pants. When you walk in the rain, the motion of your stride kicks some water up onto your legs. I can dry my skin with a paper towel if need be, but drying wet pants isn’t as easy. Aside from the A-line silhouette being my favorite, it has the same waist cinching effect as the trench coat. Furthermore, the fabric of the A-line skirt flares away from the body, so even it it were to get wet, I would barely notice because the fabric doesn’t cling to the body. Pairing my skirt with a nice top makes going out in the monsoon-like weather worth my effort.

Rain-Appropriate Bag

You don’t want your belongings getting wet or your bag damaged from the rain. Under these conditions, I always carry Longchamp’s le pliage, the original version that’s made of polyamide canvas. I own both the shoulder bag and the top handle versions. They keep my belongings dry, and the leather handles and side tabs add a hint of practical refinement to the piece.

Works Sighted

Look 1: J.Crew Factory classic trench coat; J.Crew ruffle-neck top in end-on-end cotton; Grace Karin vintage pleated A-line midi skirt (black); Longchamp le pliage shoulder bag L (black); London Undercover automatic umbrella (black); Hunter original Chelsea (gloss)

Look 2: London Undercover automatic umbrella (navy); Barbour Inglis waterproof jacket (mist); J.Crew flutter-sleeve jersey T-shirt with swiss dot; Grace Karin vintage pleated A-line midi skirt (navy); Longchamp le pliage shoulder bag L (navy); Hunter original Chelsea (navy)

Look 3: Barbour Inglis waterproof jacket (slate blue); J.Crew tie-shoulder linen top; Grace Karin vintage pleated A-line midi skirt (dark grey); Longchamp le pliage top handle bag L (gun metal); London Undercover automatic umbrella (navy); Hunter Original Chelsea (black)