Millennial and Gen Z children are dressing their Baby Boomer parents up in their clothing, revealing that our parents are still icons. 

One of my favourite things to witness is a social media trend bringing generations together, especially over a subject matter that often divides them. It’s heartwarming to witness everyone’s moms and dads slaying the aesthetic that they don’t usually get to indulge in.

The collective reaction to this trend has been overwhelmingly positive with most comments calling the trend wholesome and fun.

I was deep into this Tik Tok rabbit hole when I noticed that almost all of the parents participating in this trend not only looked great but also seemed to exude more confidence than they did in their own clothes. 

Their confidence inspired me to reflect on the nature of style as a whole, and the limitations associated with “dressing your age”. 

Oftentimes, societal and cultural expectations can cloud personal choice and expression; and it is particularly evident when it comes to the relationship between age and style.On the surface, style and clothes can feel like a frivolous and mundane topic to many people, especially to those who “don’t care about what they wear”, but there is definitely more to it.

I spoke with Gagan Nagra (@looksbygagan), a stylist, occupational therapist and PhD student, about her experience and insight into style and dressing age appropriately. 

“The conversation around style and ‘dressing your age’ is a societal expectation,” Nagra explained. “A lot of people feel this pressure over different periods of their lives, whether it's in their 20s, 30s, or 40s, that they should be dressing a certain way. This limits the expression of your personality and this pressure forces many people to dim themselves”.

Fashion can be intimidating and overwhelming for many people and it’s often related to trauma associated with concepts such as body image, societal pressures, culture, and aging, just to name a few. It’s difficult to work through the barriers in order to get to a place where you can explore what style and fashion means to you, and use it as a means to express your identity.

I was so fascinated by this space that I decded to conduct a personal experiment around it. I asked peoplefrom various age groups and diverse demographics in my life to tell me about their relationship with clothes, fashion, and style. The concept of age and the relationship with one’s body came up in every conversation, unprompted, and overwhelmingly so.

Age can be a sensitive topic and there are endless underlying factors that lead to anxiety and negative feelings when discussing aging. Many industries thrive on manipulating people’s insecurities and pushing a “fight against aging” narrative, when it’s something natural and inevitable. 

‍People dress the way they dress for various reasons: for fashion, for comfort, for the season, for functionality, for personal expression, for weather, for work, to name a few reasons. Some people put on the first thing they see, and don’t think twice about it whereas some people spend hours curating the perfect outfit, and everyone in between.

The “dressing your age” narrative feels exceedingly toxic as I speak to more and more people about it. 

Originally, I thought that people feel the need to conform and give into societal and cultural expectations regarding style because it’s uncomfortable to not do so. However, the relationship people have with their bodies has a massive influence on how they perceive style and fashion. These relationships can be very complex, nuanced, tumultuous and full of trauma no matter what age, gender or socioeconomic status a person is.

Young people are rarely taught how to actively have a healthy relationship with their bodies, and to take the time and be intentional about our clothing choices. Meanwhile, we are constantly being influenced by social media, unrealistic beauty standards, and pressure to fit in. There is immense unlearning and relearning required in order to build that relationship as an adult, and that’s no easy feat.

Human bodies are constantly changing throughout  different stages of life, and therefore the relationship with one’s body and style needs to constantly evolve as well.

Nagra sees this at play in real time with her clients and she explains, “you learn how to dress from teen years when your body is changing and you’re navigating puberty, to your 20s, to pregnancy, to postpartum, to menopause, to old age – people’s bodies are constantly changing and knowing how you feel is going to get you through that uncertainty.”

“Not everyone goes through the same transitions in life and not everyone has the same traditional beliefs," Nagra continues “so having a healthy relationship with your body comes early and it’s important to recognize that and use that as the guiding force behind your style journey, not age.”

When I reflected on my own relationship with age and style after speaking with Nagra and others, I concluded that it is a double edged sword. Often I feel damned if I do, and damned if I don’t. I constantly feel the pressure to “dress like an adult” at this stage in my life and I find myself looking for external validation about my choices rather than looking inwards.

I shared my reflection with Nagra and she corroborated that I am not alone in feeling this way. “When people don’t ‘dress their age’, they feel heavily scrutinized and criticized by society which takes a huge toll on their self image. They correct this by dressing in ‘age appropriate’ clothing which inevitably leads to a negative self image as well because they don’t feel good in what they’re wearing.”

Applying arbitrary rules of age to personal style limits the scope and benefits that it can provide. “Style is a spectrum and your age should not define where you stand on that spectrum. It’s about how you feel that day and you may feel completely different the next day. It’s just another form of expression that is too heavily policed by societal notions unnecessarily,” says Nagra.

‍Research suggests that it’s best to learn to dress for how you feel and that's exactly the difference between style and fashion. Fashion trends are always changing and it’s fun to engage in them sometimes if you enjoy it,but finding your own personal style is the most cost effective, psychologically and emotionally beneficial.

I think everyone can relate to feeling pressure at some point in regards to what they wear, and it’s important to explore these ideas that can seem unimportant but in actuality, they affect our everyday lives greatly. 

We all wear clothes everyday, and yet everyone’s relationship with clothes is so different and complicated. It’s easy to disregard style and fashion simply due to the connotations associated with those terms as an industry, but it’s an integral and deeply imbedded part of our society that deserves to be critically explored.

Nagra shared a piece of advice she has for people trying to navigate this journey, “you shouldn’t be following trends or others’ expectations but rather dressing how you feel and that starts with your relationship with your body. Learning about your body is ultimately what’s going to make you feel better – it’s your decision if you want to be a mom in sneakers and jeans or a mom in stilettos and a pencil skirt.”