This work investigates gender roles and its connection to fashion during the Northern Renaissance in comparison to modern day. Fashion facilitated aspects of sexism during the Northern Renaissance primarily through symbolic clothing and occupations held in the industry. Evidence of this mistreatment was found in many artworks of the time and cited in this analysis. Women’s clothing would also be used to identify a man’s wealth, rather than an individual’s style choices or preferences. These sentiments also stem from the patriarchal society and religious customs. To an extent, the view of women in society today has changed. In fashion, the line between genders is blurring, making social expectations based upon appearance more difficult than it was in the past, as demonstrated through photos from current runway shows. Interestingly, fashion from the Renaissance has also cycled back to influence current trends. Many scholarly articles outline women’s experience during both time periods, which draws attention to striking similarities and some key differences between the two. As for feminism today, there is still much progress to make, as many women face similar oppression to those of the Northern Renaissance when it comes to power structures, abuse, and equal rights.