CloseFacebookInstagramPinterestTwitterLogoPath 1 The Strategy Subscribe

Want More TS?

Sign up for our newsletter.


Want more TS?

Sign up for our newsletter.

Stories Diary Picks About Press Contact

Rules Are Made to Be Broken

Rules Are Made to Be Broken

Written by Sara Fender

We’ve all heard the fashion ‘rules’: Don’t wear white after Labour Day, don’t let your bra show, sequins are only for after dark, don’t wear sneakers with dresses and skirts, no crop tops after your 20s, and a barrage of other equally ridiculous directive that no self-respecting fashion enthusiast bothers to follow anymore. In fact, the only real rule to follow these days is to not follow any of the rules. The rules are made to be broken.

For example, that rose gold sequin mini dress from Revolve that you have in your closet reserved for a night out with your girl gang – let it see the light of day with a pair of white Adidas Stan Smiths and a boxy white cardigan (double points if you wear this look after Labour Day).

I have a stylist friend who didn’t start working out until she was 40, thus resulting in a body and fashion revolution. She began exuding confidence, and wearing Off White and Alexander Wang crop tops  and Valentino sheer shirts. She looks amazing, and, dare I say, better than most of the 20-somethings I see. Watching her transformation gave me the encouragement I needed to start breaking some of these ‘fashion rules’ on my own terms.

I remember the first time I ventured into the exposed bra trend. I own a sheer, dark, floral duster from Zara, that I usually wear with a white t-shirt and jeans, or over a dress, but on this particular day, I wanted to try something different. I put on a pair of black high-waisted leggings from Nasty Gal, a black strappy sports bra from Alo Yoga, threw on a pair of black boots and the duster, and went to meet one of my more conservative (think J.Crew and Ann Taylor) friends for lunch. She was already seated when I arrived at the restaurant. As she stood up to greet me and give me a hug, she whispered, “I can see your bra” to which I whispered back: “That’s the point” before she could pull away with a look on her face. You know ‘the look’…

As we talked over nachos and margaritas, she told me how she wished she could take more fashion risks, but that she felt like she couldn’t; not only because of how she was raised traditionally and she was afraid of what people would thing, but also because she was just so stuck in her perception of these so-called ‘fashion rules’ and what they mean. I told her about the other stylist and how, in watching her, I was able to stop caring so much about what other people thought, and focus more on how my own clothes and personal aesthetic made me feel. I explained that not only was I now having more fun with my wardrobe choices, but also how I was finally gaining confidence in myself and how it made a difference in other aspects of my life as well. I could see her taking it all in.

A couple of months later, I was going to an art gallery opening and invited the same conservative friend. We met up for drinks beforehand and I was shocked and impressed when she showed up wearing a pair of mid-rise skinny jeans, a Gucci double-G buckle belt, and a sheer white long-sleeve button down that (gasp!) slightly exposed her bra. I did a double take before standing up to greet her with a hug. As we embraced, I whispered, “I can see your bra” to which she cheekily replied, “That’s the point.” I’ve never been more proud.


More Diary

Road Trip Essentials Prev

Road Trip Essentials

Before COVID came around, we had many travel plans – adventures in Istanbul, a safari in Malawi, and beach getaways...

The September Issue: The Vogue 2020 Covers Next

The September Issue: The Vogue 2020 Covers

The theme of this year’s ever coveted September ​Vogue​ stems from one core word in representation of 2020: HOPE. For...

All Images Copyright 2014-2024 The Strategy