In Pursuit of Timelessness: A Conversation with Armando Diaz


Original art provided by Armando Diaz

Most digital designers do not base their company’s business practices on their clothing tastes, but Armando Diaz is not like most digital designers.


I had the opportunity to meet virtually with Diaz back in October 2020 and hear about what he has done since graduating from the University of Kentucky in 2019. He sat in his room, a cello propped against the wall, a stack of design books and magazines on his desk.


The vintage sweater Diaz was wearing was accentuated by an assortment of gold chain necklaces, matching his wire-framed glasses. He was enthusiastic, in words and gestures.

The meeting became less of an interview and more of a conversation, the topics ranging from fast fashion to life advice.


Although separated by screens, I was struck by his passion and energy.


The 24-year-old has built a freelance business from the ground up, collaborated with clients to build their branding, and continued to work full-time – all in the middle of a pandemic.


His freelance brainchild, a Lexington-based creative agency called WORKINGWITHSAINT (WWS), helps design branding campaigns for clients, mostly independent musicians and young technology startups.


Diaz wasted no time in diving into what he does and why he does it.



Armando Diaz sits for a photo on Wednesday, Feb. 24, 2021, in Lexington, Ky. Photo by Tyriq Duckwyler

Born into an immigrant family, Diaz was raised in Lexington and went to UK as a digital media and design major. While in college, he helped friends build branding for their startup companies and bands, and WORKINGWITHSAINT was created.


Explaining his agency’s unique name, Diaz said, “The place where the ‘working with’ comes from is a lot of the people we work with actually end up becoming our friends. ‘Saint’ comes from wanting to be a perfectionist and wanting to create work that’s very holy.”


Although bands and tech companies seem like irreconcilably different clientele, Diaz sees them as surprisingly similar.


“I think it’s cool because [working with] tech startups and young musicians, young bands and young artists, it’s almost the same thing – low budgets, very tight deadlines and greater rewards when you do things right,” Diaz said. “I think musicians and young entrepreneurs and young startups have the same drive and the same challenges.”


The agency’s Instagram page, @workingwithsaint, echoes this sentiment in its profile description: “Young founders and musicians face the same problem. Ask us how.”


WWS works alongside these clients and builds a public brand around their aesthetics and marketing needs.


“Focus on who you’re trying to serve and what you’re trying to do, and more importantly, create timeless work … helping people figure out who they are, what they do and why they do it, and then translating that into a design,” Diaz said, summarizing his vision for WWS.


Diaz’s business philosophy closely mirrors his opinions about the clothing industry.


As with WWS, he values timelessness and functionality in fashion above trendiness. Citing brands like Carhartt, Allbirds and Pyer Moss, Diaz spoke to the difference between inexpensive fast fashion and more costly but better-quality pieces.


He laughed, saying that he used to be a “hypebeast,” concerned more with a brand name than the quality of clothes.



One of the designs WORKINGWITHSAINT created for the Sunmates rebrand. Original art by Armando Diaz

His view of clothes and fashion has changed since then. “I’ll spend 80 bucks on a Carhartt jacket or some coveralls,” he said. “It’s going to last me. I could probably give it to my grandkids.”


Diaz pointed to the sweater he was wearing. “I’m just wearing this ‘cause I got it at Goodwill,” he said.


Diaz firmly believes that fashion is an art form, a way for individuals and designers to express their creativity and imagination. To him, fast fashion rips off artists; while more accessible and usually more affordable, those trendy, cheap clothes are mere imitations of the real things.


“[Avoiding fast fashion] puts more pressure and more responsibility on these vendors, on these artists, on these designers to think about their apparel,” Diaz said. “I’m hoping that consumer habits change in favor of that … I’m not saying I want everyone to be like me, but I feel like that’s the only way you get the attention of these execs at Forever 21 or H&M.”


This pursuit of responsible, timeless functionality permeates Diaz’s vision for WWS. From the clients the agency takes on, to the work he produces, Diaz strives to build branding that will stand the test of time.


“If you were a client, and we’re working on a brand guidebook, I wouldn’t want to put you in a lane that’s super trendy today,” he said. “I’d want to create something that will last you for quite a while.”


WWS is able to produce this curated branding by building relationships with its clientele, relationships that often develop into long-term friendships. However, due to the extended time the company devotes to each client, and because he and the other five WWS employees all have other full-time jobs, Diaz and his team have to be selective with whom they work.


“It’s not because we’re snobs or anything, but it’s a two-way street, and a lot of these projects are long term. You’re talking about a least a month of working together,” Diaz said.

The company originally started out working primarily with independent bands and music artists.


“A lot of it came down to working with musicians and experimenting with what musicians need and how we can help them,” Diaz said. “We’ve transitioned from being a creative agency to now an art house where we focus on working with more musicians at any caliber, at any level, at any stage in their career, just for the sake of doing creative work with people who are responsible.”



A design WORKINGWITHSAINT made for the AGIFT rebrand. Original art by Armando Diaz

One of the agency’s first clients was singer Soma, KRNL’s cover model last spring. WWS worked with Soma to build her branding and helped her land the opportunity to work with indie band Empress Of. The WORKINGWITHSAINT Instagram includes several posts featuring Soma from the branding campaign.


WWS has also collaborated with Korean clothing designer Doin’mathang, whose avant garde styles are taking Seoul street fashion by storm, according to Diaz, as well as rapper AGIFT.


Since I spoke with Diaz in October, WWS has collaborated with indie band Sunmates, helping them with an entire rebrand and new website design in conjunction with the release of their newest EP.


Diaz said he relates to these young bands, referring to the struggles that come with starting any venture, be it forming a band or building a business.


WWS is also branching out to work with other businesses, such as technology companies. For example, the agency worked with Vividcharts, a tech company specializing in creating accessible, curated data reports for businesses.


Work for the agency has not slowed, despite COVID-19; in fact, Diaz said the pandemic brought some positives for his business and its clients, particularly the musicians.


Bands have not been able to have in-person concerts in the usual venues, but Diaz sees this as a blessing in disguise.


“I’m not a huge fan of venues,” he said. “They sort of rip off musicians, so everything’s changing now to be more digital and changing to creating and connecting with people via your phone.”


He also sees this shift toward more virtual methods of hosting concerts as giving bands more leverage and cutting out any overhead costs with the venue rental. As a result, more of the earnings from admission and merchandise sales go directly to the band.


“I think we’re going to see a shift where musicians will have that leverage, where they can just do this on their own even more,” Diaz said. “Would you rather host your EP at your friend’s backyard or do it at a venue where you have to make your audience pay and you only get a certain amount?”


Diaz believes it is important for people to not only know what they are doing with their lives but why they are doing it. “Don’t ask yourself ‘What do you want to do?’ but ‘What do you want to solve, and what do you want to contribute to any field or focus that you’re interested in?’” he said.


He also had advice for anyone trying to figure out what they want to do in life. To him, responsible work stems from building or creating something that will benefit and is accessible to others.


“And I definitely recommend hanging out with designers!” he said, laughing.