Olascuaga began her pageantry career representing the department of Bolívar in Señorita Colombia on November 12, 2018. She placed first runner up, being awarded the title of “Virreina”, but resigned the following day. On November 16, 2020, Olascauga, representing the department of Bolívar, won the title of Miss Universe Colombia 2020 and was crowned by former Miss Germany and current director of Miss Universe Colombia, Natalie Ackermann. As the new titleholder, Olascuaga will represent Colombia at Miss Universe 2020.