Off-Duty Models, Then & Now

Off-Duty Models, Then & Now

Over the last few years, we’ve seen a rise in the popularity of the “off-duty model” look. From hair, to makeup, to outfits that take the beloved “athleisure” comfort to the next level — creators, stay at home moms, and corporate 9-5 girlies are pulling inspiration from the ones who do it best — the models themselves.

If you know me, you know that anything from the 90's makes me swoon. Earlier this weekend I was watching Before Sunrise and thinking to myself, how lovely it would have been to live in the 90’s, traveling on a train from Budapest to Paris enjoying casual conversation.

The fashion, the simplicity, the way I picture living in New York City with the same “grain” effect we see in the movies when we watch them now — it all seems so lovely.

I digress.

The reason I’m bringing up the 90’s is because a lot of the looks we are seeing from Kendall Jenner are looks I can also find in a picture of Cindy Crawford from 1991.

So today, we are going to travel back in time to see what some of the top models were wearing back in the 90’s, and then we’re going to bring it back to the present to see similarities in some of our top models outfits today.

The 90s Girls

Cindy Crawford

Oh Cindy, how we adore you.

Cindy Crawford was recently featured in a documentary about some of the first top models. They followed the conception of her career and how she got to where she is today.

The documentary showcases some of her biggest moments in fashion and how she was one to take her off-duty looks up a notch.

She was regularly pictured in basic tops paired with high quality denim, cool jackets and her hair down — providing an “undone” look that looked absolutely flawless.

Kate Moss

Am I the only one who didn’t know Kate Moss dated Johnny Depp? They were cute together, but she’s moved on.

Moss was first known as a sort of “anti-supermodel,” taking her rise in the late 1990s and being photographed in a more “grunge” like style than the models in previous years, as rock was on the rise.

It was really hard to choose just a few photos to include here because she wore sooo many good outfits, but here are a few where she featured simple tees, sneakers, and even an all white look that’s giving “quiet luxury”.

Christy Turlington

Another model featured in “The Supermodels” documentary was Christy Turlington, who was once known as one of the most famous supermodels in the world and was showcased in many, many Calvin Klein campaigns. She is now a maternal health advocate, director and yoga practitioner.

Christy put together looks that had a more casual vibe to them (jeans, sweatshirts, etc.), but most of her looks had a sense of elegance intertwined.

For example in the third photo, the length of her sleeves, small white shoulder bag and almost bare face make her look like she just stepped off the runway for a meet-and-greet. Beautiful!

Modern Day Looks

Now moving on to our modern day models! As I said before, we’ve watched the rise of the off-duty model look over the last two years, and even as trends evolve, I continue to see some form of this style trend in my social feed every day.

In other words, it’s here to stay — at least for now 🙂

Kendall Jenner

I will never forget watching an old episode of the Kardashians where Kendall talks about how she wants to “make her own way” as a model, not relying on the fame she had from her family. I instantly had more respect for her, and since then, have watched her blossom in her career.

If I had to pick one “cool girl” to find inspiration from, it would be her. And above all else, it’s because her style feels attainable! She is consistently seen wearing looks that can be pulled together from simple, staple wardrobe pieces.

10/10, every time.

Gigi Hadid

With 45 appearances in International Vogue, a clothing brand and ridiculously beautiful maternity photos, seeing Gigi Hadid grow in her career has been so fun.

While she sported more “tom-boy” looks in the past, a lot of her more recent looks have been more refined. Think: more blazers, cashmere sweaters (including her own designs!) and trousers.

These are some of my top faves!

Hailey Bieber

Slick back buns, clean girl makeup, and incredible street style can all be attributed to Hailey Bieber. She has taken TikTok by storm via trends and her personal page.

While Hailey was already widely known in the industry, in more recent years she has really taken off in her career as both a model and business owner who’s street style is off the charts. Her focus on low-rise denim, the coolest sunnies, and sneakers has her constantly being featured in online magazines!


All in all, it’s really cool to see the models we know and love pulling inspiration from women who played such a big part in building the industry as we see it today.

Through picture, career and style, there are many similarities to be found amongst them all. This post showcases only a few of their more recent looks, and I am so excited to continue watching as their street styles evolve in the years to come.

Cheers to taking it back to the 90s!

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Madison King

Madison Leigh King is an author, writer and copywriter from North Carolina. Avid reader turned writer, she draws inspiration from her favorite works and interweaves personal experience into what she creates. She loves sharing stories, moving her body and slow mornings with her husband in their Southeastern home.

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