Katy Keene struggles to manage the pressures of her day job at Lacy's Department Store and her very demanding boss, Gloria, who is a legendary personal shopper. Lucky for Katy, she has the support of her longtime boyfriend, KO Kelly, who has his own dream of becoming a professional boxer and a surprise Katy wasn't expecting. Katy's roommate and close friend, Jorge auditions for a Broadway play, but it doesn't go as planned and he tries a different route to potentially get noticed. When Katy meet her new roommate Josie, she knows they will be fast friends. Josie meets record producer Alexander Cabot, but it is all seems too good to be true when Alexandra Cabot gets involved. After a long day, the group of friends, including 'It' girl Pepper, all meet at their favorite hangout, Molly's Crisis, to watch Jorge perform as his alter ego, Ginger, and to see Katy's latest fashion creation.
With Katy's personal life in a holding pattern, which everyone seems to know about thanks to the newspapers picking up Pepper's blog, she can't seem to escape even at work. Josie finds a job to help pay the bills but picks up an extra job at a record store, and quickly learns it might be closing, leaving Josie with an idea to help keep it open. Because of Jorge's outburst at his last audition he finds himself on the outs with the Broadway community. After begging for one last audition and waiting to hear if he got the part, he must decide if he wants to give up performing as Ginger. Meanwhile, Pepper finds herself low on cash, but is somehow able to secure a warehouse in which she dreams to open up "The Pepper Plant".
With everything a little off between Katy and KO, Katy tries to make everything perfect for Valentine's Day, so she can avoid what she is truly feeling including lying to him about Gloria making her work. KO tries to do something nice for the roommates, but only seems to make things worse. Josie and Alexander have been growing closer, but after she meets another aspiring songwriter, Josie realizes it's time to change up their dynamic. Jorge has been in a secret romantic relationship, but after he doesn't show for his performance at Molly's Crisis, Jorge realizes what he needs to do. Meanwhile, Pepper turns to an old friend, Ms. Freesia, to help her get some quick cash but isn't proud of how she is doing it.
Katy enlists Pepper's help to save her job. Meanwhile, Jorge questions his new relationship. Josie confronts the Cabot siblings.
With Katy trying to get into fashion school, she knows she needs a recommendation letter, so she turns to Gloria who puts her to the test in making her the ultimate dress in exchange, putting the pressure on Katy. Forced to stay inside because of the polar vortex, tensions grow high when Josie and Pepper get into a fight and Jorge breaks Katy's number one rule. Meanwhile, Josie is torn about the deal Alexander's dad made her, especially after what Alexander shows her.
With Katy trying to move on from KO, she once again throws herself into her work, which turns out to be a sticky situation with her clients. Pepper is confronted about what she is up to but is surprised about the proposal she receives instead. Jorge learns he might be losing his coveted performance spot at Molly's Crisis to the winner of a drag queen pageant, so Jorge decides to enter Ginger and is surprised by his mother's reaction. Meanwhile, Josie is nervous about her mother coming to town to hear her EP release and of course meeting Alexander.
Gloria is putting pressure on Katy to design a wedding dress that would be career changing for her. Jorge wants to keep pushing his career forward, so he decides to put on a show. Josie is frustrated that nothing has come from her EP party. Meanwhile, Pepper turns to Alexander and Xandra for an investment opportunity.
With everyone reeling from what happened to Jorge, Jorge must now explain to his dad about Ginger. Katy is vying for an important apprenticeship, but in order to earn it she is given an impossible task that involves dealing with Xandra. The group all wants to celebrate Pepper's birthday like in years past, but this year she does something a little different, but her plan gets hijacked by Ms. Freesia. Meanwhile, Josie is eager to get her music out into the world, so she shoots a music video behind Alexander's back.
Katy struggles with find her place with her new position and loses her confidence and turns to Gloria who gives her good advice. Alex wants to put together The Pussycats again, but what his dad envisions and what Josie envisions for the group are two different things leaving Alex to make a tough choice. Jorge is happy that he is able to bring his current boyfriend and a budding friendship with an ex together, but things become a little messy. Meanwhile, Pepper is in an online feud that could ruin everything for her, and she is stunned when she learns who it is.
When an allegation against Gloria is made, Katy tries to get to the bottom of it, but instead might have discovered something about her mother. Josie and the new Pussycats have a falling out leaving Josie's close friend, Kevin Keller, to remind that she doesn't need to be that person anymore. Jorge offers Bernardo an interesting relationship proposition in order not to lose him, but it does not go as he hoped. Meanwhile, Pepper's past is starting to catch up with her and it could jeopardize more than just the Pepper Plant.
With the pressure of the Meta Gala, Katy is being pulled between her new roles. Pushing through everything, Katy takes a designing risk for the Meta Gala that she hopes pays off and top everything off, Katy hears back from Parsons. Pepper goes head to head with her foe by making a splash at the Meta Gala to help promote Josie and the Pussycats and The Pepper Plant, but all might end badly when her foe gets to Alex. Jorge decides to figure himself out, but her learns some surprising information about his parents. Meanwhile, KO asks for Katy's help and KO finds himself sticking up for Katy, which could put her job in jeopardy.
With the Pepper Plant opening, Pepper is excited to finally show it to off to Katy, Josie and Jorge. Thinking Pepper is in trouble, Josie tells Katy and Jorge what is going and on and they are starting to see that things aren't adding up quite right. Katy finds some unsettling information about Guy's past and must decide how to handle the situation. Meanwhile, Jorge takes on a few extra jobs to help with his parents' financial predicament.
Katy is starting to see things a little more clearly and needs Gloria's help to make her plan work and it leads her to unexpected opportunities. Eager to make things right, Pepper finds a way to make it right with Jorge and Josie, but she must also try to let go of people in her past. Jorge holds a rally to stop the sale of his parents building, but he has no idea who he is going up against. Meanwhile, Josie is worried about Alexander and turns to someone unexpected for help.