2015 was a really hard year when I look back on it. It was the year when the reality of being a business owner truly started to hit home. At the time, I was frustrated and feeling a little lost, even though I have since come to appreciate the idea that creativity often emerges when constraints are applied. In that moment, it was far less romantic and much more challenging.
The year began with an early decision to produce more Oxford shirts and sweatshirts. With hindsight, I might have pivoted away from Oxfords and leaned more heavily into casual wear, focusing on sweatshirts, T-shirts, and everyday staples. Still, the shift in design toward a simpler sweatshirt stands out as one of my prouder moments from a business and design perspective. Those sweatshirts went on to become the best-selling item in the store and validated the idea that restraint and clarity often lead to stronger products. The Oxford shirt also evolved during this period with the addition of a pocket, something it arguably should have had from the beginning.
As financial and operational constraints tightened, difficult decisions became part of daily life. There were times when producing clothing meant not taking a paycheck, skipping dinner, or delaying rent, all in service of keeping the business moving forward. That lack of resources, while stressful, also pushed me to explore new creative paths. I began spending more time on a sewing machine, producing simple items in the shop and learning through hands-on experimentation.
Collaboration also became an important outlet. I worked with my uncle, Matt DiCastri, to produce a series of printed T-shirts that added variety to the collection and brought fresh energy into the store. The Fall/Winter 2015 season introduced a run of flannel shirts that were fairly well received and, in a very real way, helped keep the lights on just a little bit longer.
