Middleton, a new women’s clothing store, is opening in Middlebury | Popgen Tech
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A new women’s clothing store recently opened in downtown Middlebury. Middleton, located at 66 Main St., is co-owned by Alyssa Kestner, owner and manager of Monelle Vermont — two boutiques in Burlington and Shelburne — and Lisa Phelps, owner of Middlebury Salon and Spa.
Last spring, Kestner and Phelps received a $20,000 KickStart grant through the Better Middlebury Partnership to help them open the store. The store’s website describes Middleton as “a clothing and lifestyle boutique for the smart and stylish woman.” It sells an assortment of clothing and accessories, jewelry, stickers, postcards, and more.
Kestner, who grew up in the Boston suburbs, has ties to both Vermont and Middlebury College. She attended Bates College and worked at Merrill Lynch until the 2008 market crash. After the accident, she moved to Vermont for a change of pace. She started working in retail at Monelle and eventually bought the store in 2013.
In a phone interview with The Campus, Kestner spoke positively about the business Middleton has received since opening. “It was a really great introduction to Middlebury,” she said. “It’s been a really amazing and consistent reception from both the city and the college students and parents.”
Kestner said she hopes Middleton can become an oasis for college students looking to get off campus. She compared the affordability of getting off campus in Middlebury to her experience at Bates, where there was no local town and the closest city was Portland, Maine.
“To be able to get off campus and have things to do and things to see and almost like a little dose of home… I think it was a no-brainer [for students]. [At Bates] We didn’t have any way to support the local community or … get off campus for a few minutes, so I hope this is something Middlebury students will enjoy,” Kestner said.
Several college students also work in Middleton, something Kestner is familiar with. “I’ve been at Monelle Burlington for over 10 years and I’ve had a lot of college students over the years,” Kestner said. “I love visiting college students, and I respect any college student who wants to get a part-time job in addition to their studies…I understand that you’re in school and that’s the most important thing, but I can also say that the staff is very like to do anything that gives them more structure.’
Kestner also said she aims to show students a wider range of possible uses for their degrees in the future. As an economics major in college, Kestner said she was “laser-focused” on pursuing finance and never realized what other business options there might be. “All businesses have the same structure and operation, and it’s a matter of how you give them a creative approach,” she said. “I was really excited to give the students a chance to see the store open from the ground up.”
Alice Provost, manager of the Middleton company, is one such student. The provost attends a university other than Middlebury and took a semester off to learn about entrepreneurship through her work at Middleton.
“A typical day focuses on helping clients in any way they need,” the provost wrote in an email to The Campus. “The customer comes first. When we are not busy [with customers]there’s a lot of cleaning and unpacking orders, and picking up some outfits to sell merchandise.’
She added that she learned a lot from her experience working at the store, especially in terms of her communication skills while interacting with customers on a daily basis.
“I think the store has been a great product for the town and the college. We have some essential items that are hard to get without traveling to Burlington… I hope the store offers a more convenient place to shop that takes some of the hassle out of being in a remote town and shopping online,” added Provost.
According to Kestner, the process of buying inventory for a store is largely influenced by what customers want. “I don’t have a background in fashion or merchandising,” she said, “so I buy what I personally like, and then we really try to read the customers.
Kestner added that Phelps’ insight as a Middlebury resident and store owner of five-plus years has helped determine what customers want in the city and the college.
Middleton buys inventory year-round, usually two seasons in advance. At the same time, they often reserve some of their purchasing power for immediate use to see what people are looking for and bring products on demand. Currently, the store cooperates with about 25 brands, but this number may fluctuate over time.
In a follow-up email to The Campus, Kestner elaborated on the thought process behind selecting merchandise. “We have a variety of price points to meet the needs of different demographics. We take great pride in the quality and design of our high-end products, understanding that some items are investment or everyday practical,” she wrote.
This range features items from Burlington-based brand Commando, which creates leggings, bodysuits and trousers in luxurious technical fabrics designed to be durable and comfortable. Middleton also has brands such as Grade & Gather, which makes sweaters, and Just Black Denim, which is made in the USA and includes a range of denim options.
At Middleton, Commando pants retail for $278, Grade & Gather sweaters are $40 to $70, and Just Black Denim is $90 to $120.
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“There are so many options online at every price point that it can be difficult for a consumer to navigate quality and fit,” Kestner wrote. “Our job as a buyer is to curate a collection that works for our customers.”
Looking to the future, Kestner said she hopes to sell Middlebury Custom Equipment. “I love finding brands that I’ve worked with that I really like and asking them to customize it for me,” she said. She previously worked on custom equipment at Monelle Vermont.
Kestner added that she also hopes to have events in Middleton that attract students from the college and the town, such as hosting a jewelry-making workshop.
“I’ve been very pleasantly surprised with what the city of Middlebury has to offer and what we’re getting out of it as well,” Kestner said.
Middleton is open from 10am to 6pm Sunday to Tuesday and 10am to 7pm Wednesday to Saturday.

Julia Pepper ’24 is local editor for The Campus. She previously worked as a staff writer and wrote about local businesses and events in Addison County.
She is undeclared but plans to study psychology and political science as well as French.
In her free time, Julia likes to meet with friends, read, bake and ride a bike.
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