For three decades Tom Maloney has been providing contemporary, modern menswear to customers throughout New Haven. Specializing in fashion that looks great whether dressed up or down, Maloney’s concept transformed into Raggs - Fashions for Men. While now a fixture in the downtown New Haven area, Raggs opened in 1984 on the day after Thanksgiving in northern New Haven. The Westville location lasted until 1988, with Maloney and Raggs moving to 1020 Chapel Street, where to this day customers can get everything from a well tailored suit to forward thinking casual wear. On the eve of his 30th anniversary in business, The Raggs Bag spoke to Tom Maloney about the history of Raggs, New Haven and the evolving culture of men’s fashion.

The Raggs Bag: When you opened Raggs, what was your initial vision? Has that vision changed or evolved over the years?

Tom Maloney: Our initial vision was to be men’s and women’s. When we moved to Chapel Street, the focus was menswear. We opened the day after Thanksgiving, so my initial goal was to last until at least Christmas.

The Raggs Bag: In the three decades that you have been in business, has there been a fashion trend that you especially liked? Has there been a trend that you didn’t like/understand but was still popular?

Tom Maloney: What I do like is modern fitting clothing. It just looks better on everybody.
The one trend that took me by surprise was the sock craze. Fun, comfortable and jazzy socks have made quite the stir! Brands like Ted Baker, Happy Socks and Ozone have created striped, dotted and printed sock options for a man looking to add a pop of color to their work attire. Before the “sock craze,” black, navy and grey socks were the only colors we stocked for the past 25+ years.

The Raggs Bag: What one item has always been a constant? That one item that never really changed and has always remained fashionable, no matter whether you purchased it in 1984 or 2014?

Tom Maloney: Fashion is always evolving. The consumer need to feel and look their best has remained constant, but apparel and menswear changes season to season. Certain key items like a crisp white dress shirt changes in design, new fabrications are used and fit becomes more or less tailored. A crisp white shirt tucked into the back of the closet collecting dust with a huge collar shape that may have been “trending” in 1984 does not count as having a white dress shirt. Key items are the most important to keep fresh and updated. A crisp, well fitting white dress shirt is essential to every man’s wardrobe.

The Raggs Bag: When you are putting together a collection for Raggs, what is the mindset?

Tom Maloney: I make sure the collection has consistency. All of the brands we carry have their own unique spin on the season’s trends while remaining sophisticated and current.

The Raggs Bag: A lot of the current Raggs stock consists of European based labels. Is that a coincidence, or a preference?

Tom Maloney: It’s a preference, these Northern European and Scandinavian brands such as Hugo Boss and SAND have a progressive look and a modern fit.

The Raggs Bag: What would be the five staple items that every man should have in their closet?

Tom Maloney: Sand sport coat, Zachary Prell shirt, Theory pants, Hugo Boss shoes and JBrand jeans. All of which can be found at Raggs, coincidentally ;)

The Raggs Bag: Looking back on the history of the shop, what have been some of your proudest accomplishments?

Tom Maloney: Generally, most men don’t realize they need something until the 11th hour. For us, it’s the norm to have a customer need an entire outfit to wear right away. I’m proud of the fact that I can provide same day or next day alterations.

The Raggs Bag: As a small business owner, what do you think is the key to longevity? More specifically, what has been Raggs’ keys to longevity?

Tom Maloney: I think the key is to have an interesting product; it has to be well merchandised. The customer needs to be greeted by a competent and enthusiatic sales person. I have a blue collar work ethic and I work hard at maintaining this standard.

The Raggs Bag: You have been in New Haven now for the entirety of Raggs’ existence. How has the city changed since 1984?

Tom Maloney: The downtown core has steadily gotten stronger over the last five years. Westville (Raggs 1st location from 1984-88) was convenient to people in northern New Haven but now we are more centrally located in downtown New Haven for wider convenience and the ability to see the city grow. New Haven is on the verge of a renaissance.

The Raggs Bag: Where do you see men’s fashion going?

Tom Maloney: Down the tubes. I see people going back to a more dressed up look. The DNA of Raggs is dress clothing.

The Raggs Bag: After 30 years, what has been the biggest lesson you’ve learned?

Tom Maloney: The biggest lesson I’ve learned in my retail experience is : It’s who comes in, not how many.