Skye Gosen, a New York based fashion designer, has always felt clothes should be well-made, timeless, and make one feel like the confident best they can be. When she parts company with her employer over differences in opinion - they wanting to produce trendy, disposable clothes, in believing that clothes are as short lived as long as the fad of that trend lasts - and takes a break from the relationship with her boyfriend Patrick Scott, a fashion buyer for national clothes retailer Fromans, in he always coming up with an excuse not to take their relationship to the next level, Skye believes it's as good a time as any to pursue her dream of producing her own line, "Maybelle" in honor of her grandmother who inspired her in this work. Patrick has convinced his employers at Fromans to distribute Maybelle Fashions only if Skye can demonstrate that there is a market for her fashions using a sales and social media metric. Refusing to go the online route in believing people need to try on the clothes they are going to buy, she ends up partnering with Jason Ryder, who has gone from one start up business to another, he having no idea about fashion as witnessed by his own attire. What they come up with as a strategy is "Maybelle on Wheels", a mobile business which will allow Skye to meet and interact with her customers while having less overhead than a bricks and mortar store. As Skye and Jason start to fall for each other, hurdles in they being open to expressing their feelings for each other include if Jason believes Skye and Patrick are meant to reconcile, if Skye believes Jason not ever having stuck it out with any of his businesses also applies to relationships, and if Skye "sells out" in pursuing the Fromans contract at the expense of her own vision for her work and thus the business.
