FOTM: Mr. Greenwald


Upper School math teacher Michael Greenwald does not mess around when it comes to his outfits. From his day-to-day clothing to his extravagant festival looks, Mr. Greenwlad is always showcasing an outfit that makes him feel like his best and most confident self. 

Mr. Greenwald characterizes how he dresses under two categories: Friday and Sunday. Now, you may be wondering, just as I did, what makes an outfit fit into Friday or Sunday? “Friday outfits are basically outfits that you can wear confidently anywhere,” he shared. “It has a statement piece, at least one accessory, and everything else is pretty much plain.” 

Sunday outfits, on the other hand, fit into what he refers to as the “lazy, crazy spectrum.” If you see Mr. Greenwald walking around in an outfit such as bright blue shorts and a bright pink shirt, you can trust your gut instinct and know that he is confidently showcasing a Sunday outfit. “Sunday outfits you wear when you wanna make sure that people know you feel good about yourself,” he said. 

Along with the weirdness that may come with his Sunday fashion, he recognizes the shift to preppiness in his Friday looks. In terms of Friday outfits, Mr. Greenwald is essentially shopping at Lululemon and Banana Republic. “There’s a level of preppiness where I am that I just can’t deny,” he said, laughing. 

When shopping for Sunday outfits, Mr. Greenwald likes brands such as Chubbies and J Crew. “I’ll also go with smaller, niche brands,” he said. “So something that popped up on TikTok for me months ago and that I now have four pairs of are overalls, the sweatshirt overalls.” You’re reading this correctly: Mr. Greenwald has found great comfort and style in sweatshirt overalls. 

In terms of core colors in his wardrobe, Mr. Greenwalds centers his outfits around a mixture of three colors: tan, beige, and maroon. He also enjoys being able to coordinate different pieces of his outfits, making sure that everything down to shoes, belts, and necklaces fits well together. “For days that I am wearing something darker, I will try to go with larger pieces of jewelry,” he said, “a heavier chain or a locket.”

Mr. Greenwald’s accessories are something that always change with his outfit, but one accessory that he cannot leave the house without is his watch. “My watch is my least stylish thing, yet I can’t complete an outfit without it.” 

As we head into the wintertime, Mr. Greenwald is really looking forward to boot season. “I’m looking forward to bringing out the Tims, bringing out the Blundstones,” he said. “I have the New England LL Bean essentials.” Mr. Greenwald encourages people to shift towards earth tones in their outfits for the winter months. “Colors that feel a little bit calmer and more muted,” he suggested – colors like heather green, maroon, and tan. 

Mr. Greenwald urges readers to put effort into their outfits so that they can feel like their best selves every day. “The only piece of your outfit that you aren’t putting effort into is your backpack,” he said. Whether you choose a Friday outfit, Sunday outfit, or something in between, Mr. Greenwald encourages you to take risks within your style choices and find clothes that make you confident.