Several of my friends and coworkers do that. All of them have gotten covid. N95 masks reduce the risk of getting a respiratory disease, but they're nowhere close to foolproof.
A CDC study found that people who wore N95 masks were 83% less likely to get covid than people who wore no mask,[1] but that overstates their effectiveness. People who wear N95s tend to behave differently than people who don't wear masks. They get vaccinated more, avoid gatherings, and generally try to reduce their risk of infection in other ways. Also the timing of the study is important. It was conducted before more infectious variants such as omicron were around. And since it was conducted when California required masks indoors, only 5% of participants claimed no mask usage. So the study compared N95 people against the most hardcore anti-maskers, not the typical person who doesn't wear a mask these days.
It is for these reasons that I would bet that the real effectiveness of N95 masks is around 50%, not 83%. Useful, but not something that lets you go back to normal life risk-free.
1. https://www.cdc.gov/mmwr/volumes/71/wr/mm7106e1.htm