What To Wear: The 5 Types of Fashion Seasonal Weather Warriors

I live in New York City where people watching is not just a pleasurable pastime, but pretty much unavoidable in a city of pedestrians and close quarter subway rides. A few times a year during those weeks between seasons when the weather yo-yos between hot and cold or wet and dry, I have a lot of anxiety about how to dress. When I look to my fellow New Yorkers for guidance, I also see confusion.

I’ve observed 5 types of between-seasons dressers. See if you recognize them:

This dresser is ruled by the calendar. If it’s March, she’s wearing long pants, boots, jacket, scarf and hat – even if there is a fluke stretch of 70 degree days. A cold snap in August? Doesn’t matter, August=shorts and a tee. She’d go naked before wearing white after Labor Day.

This dresser is regulated by the thermometer. She checks a weather app on her phone incessantly and may have a secret “Weather on the 1’s” tattoo. She keeps a cardigan or scarf in her bag at all times to calibrate for minute temperature changes. This approach to getting dressed in the morning takes vigilance and dedication and I admire the confidence and chutzpah it takes to stride around (albeit in perfect weather synchronicity) wearing sandals and a sundress on a hot January day.

This dresser confounds and fascinates me. As if experiencing one type of weather on the upper half and another on the bottom, this dresser can be seen sporting a tank top and furry UGG boots together. Her flip-flopped feet are at the beach while her scarfed neck is at the mountains. Last spring I saw a woman wearing a knit red cap and scarf, dress and sandals. I couldn’t understand this.

This dresser has a steadfast preference for either her warm weather wardrobe or her cold weather wardrobe. She dreads the start of her less-favored season and holds on as long as possible to her favored one. Like holiday-lovers who start listening to Christmas music on November first, she jumps the gun when her preferred season is approaching, eager to break out her beloved fall boots at the first orange leaf sighting or her prized sandals on the first prematurely sunny day of spring.

This rare dresser gets it just right every time and makes it look natural and effortless. This dresser has an abundance of innate style confidence and is often the same person who never seems to sweat even on the hottest days. She is the dresser reading this thinking “Is this really so hard? What’s wrong with these people?”

Are you one of these dressers? Do you have any change of seasons fashion advice to share with the rest of us?