Chris Macksey and Brandy Lesser, co-founders of the newly opened Haberdasher Wine & Provisions, knew they had a piece of history on their hands.

“We bought the building in 2023. Our family was interested and had loved the building. It had been operated by the Shaffe brothers for just shy of 90 years,” Macksey said.

Shaffe’s Men’s Store operated at 475 Main Street since 1962, but the business traces its history in Bennington to 1932.

“Over the course of the year, that we were renovating it, we were kind of like looking at what the downstairs was and what it could potentially be,” Macksey said.

An observation the pair made one day – all of the cubbies that used to hold fitted shirts; looked like they would probably fit a bottle of wine.

“We grabbed a bottle of wine, put it in the shirt cubby, and lo and behold, it fits. It fits it perfectly,” he said.

The next step – a name.

Macksey and Lesser wanted to pay homage to the historic tailor shop, while still being true to the business. Then they came across the word “haberdasher.” It’s defined as a dealer in men’s clothing – and when the pair did a little bit of digging, they found even more meaning.

“We found that, actually, back in the Prohibition era, the term haberdasher was almost sort of coyly used also to reference going to get alcohol,” Lesser said.

Haberdasher is filled with products that people likely haven’t seen before.

“We wanted to bring in regions that people hadn’t ever even known, produced a really wonderful wine,” Macksey said.

The shelves are filled with wine from places like Croatia and Slovenia and Georgia, and Slovakia.
You can also find Asian and European pantry items.