The Merchant City restaurant has long been a haunt of his father, Joseph, who laid the foundations for what grew into ACS when he opened his Gilt-Edged menswear store on nearby Saltmarket 40 years ago.
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Gilt-Edged is still trading and under the Freedmans' control, but the business it is part of is a very different - and much bigger - concern to the one Joseph established.
These days, ACS operates from a 190,000 sq ft site in North Lanarkshire's Eurocentral Business Park, overlooking the M8 linking Glasgow and Edinburgh.
Home to ACS since 2012, it takes orders placed through retailers such as Burton, Debenhams, Slaters Menswear and Austin Reed, and processes them automatically through a stock control and garment sorting system.
The company invested £4 million in the kit, which processed 400,000 garments from UK orders last year. While much of the operation is automated, ACS retains a strong need for staff, and employs 100 to carry out functions such as pressing and dry cleaning.
Many staff previously worked at the former Daks Simpson clothing plant in South Lanarkshire.
To get a sense of how ACS evolved into the business it is today, the clock must be turned back a couple of decades.
As Richard Freedman recalled, that was when he and his father realised their future lay beyond selling suits. He said: "We found it was quite difficult competing with Slaters in Glasgow. Selling suits as an independent retailer was quite difficult, so about 20 years ago we started doing kilt hire.
"That grew to be really quite successful, so we basically got rid of all the suits.
"It was quite reluctantly we went into formal hire. But clearly, in hindsight, it has commercially been good for us."
But Highland dress is only part of the tale. Mr Freedman, who joined full-time after graduating in economics and marketing from the University of Stirling, said they had other ambitions when they set up ACS in 1997.
Having named the firm the Advanced Corporatewear Solutions, it set out to supply uniforms and footwear to the fire brigade and police, and firms such as IBM.
Mr Freedman said: "The corporate wear started at pretty much the same time as the hire wear. ACS set up to focus on corporate wear so we called it wrong. The hire wear really was the bit that started to take off."
By 1999, the company had thrown its weight full square behind kilt hire, consigning the corporate wear project to the scrap heap. Mr Freedman believes the strength of any business lies in recognising its strengths.
He said: "If you can't be the best at what you are doing, find something else. With formal hire, there are things we can do to be the best at that - data management, much better reliability of service, knowledge and being able to clean things and manage the process.
"Really, it's about finding something you can do better."
As the company's reputation for Highland dress hire blossomed, it moved into other formal wear.
It then struck an alliance with Blackburn-based Etiquette Formal Hire.
The idea was to offer national retailers a combined formal wear service, with Etiquette supplying top hats and tails and the Scottish firm offering Highland wear.
It worked well initially, but after seven years the relationship began to sour.
Mr Freedman said: "What we found was that, as Etiquette had grown, they had struggled to put the management systems in place for a growing business, and a lot of our joint customers became a little bit less happy with the quality, especially Slater Menswear.
"We had brought Slater Menswear to them in 2004. Slater wanted to achieve a very high standard with their hire, and Etiquette really weren't able to deliver that."
The formal split with Etiquette came in 2006, and while Richard concedes it was not an amicable parting of ways, he insists it was a "commercial inevitability".
He said ACS had become increasingly concerned its link with Etiquette was jeopardising the investments it had made to secure its future in formal wear, most notably the 25,000 square foot facility it moved into in 2002.
That unit was developed with support from Clydesdale Bank, and a Regional Selective Assistance (RSA) grant.
Mr Freedman said: "We were very much the junior partner in the relationship [with Etiquette], which was fine.
"But when the dominant partner is dragging you into areas and not doing [things] the way they should be done, your ability to influence it is quite limited. So we began to get nervous about the investments we had made."
The episode concluded when Etiquette fell into administration and was eventually bought by ACS in 2011.
Since then the business, whose kilts are made in Motherwell and sporrans in Edinburgh, has not looked back.
ACS generates about one-quarter of its sales in Scotland, with more and more coming through its customers' websites.
The firm's Xedo software arm develops "white label websites" for its clients, which consumers then use to browse the selection. Once the order is made, the consumer picks up the outfit and tries it on in store, and can request alterations if necessary.
A funding package worth £8.5 million recently secured from the Business Growth Fund has been earmarked to furthering its e-commerce platforms, it particular its Xedo software.
One of its online services, the wedding management tool sortmyweddingoutfit, allows wedding party members who live in different parts of the country to organise their outfits at a single source.
Mr Freedman, who is mulling plans to expand the business overseas, said: "We think there is always going to be a strong role for stores on the high street, but clearly having a strong online presence is very important now.
"All businesses and brands, we believe, will get an increasing amount of their revenues online in the years to come.
"It is a core for us - making sure we are able offer a full multi- channel platform for the customers we supply, so their customers can book online, manage their order online, pick it up in store, click and collect, [or opt for] home delivery."