Style Evolution: A Look Back from 21 to Now

Kait Jensen

Those cringe worthy photos from 21 and prior might be some of my absolute favorites to look back on. The style choices- bold colors, patterns, layering tank top upon tank top. Yup. You know exactly what I’m talking about! I have always enjoyed style and, for the most part, keeping up with trends. I am a firm believer that “if you look good, you feel good.” And one way I have always kept myself feeling good is by finding a style that has worked for me through all phases of life.

The Early Twenties: Experimentation and Finding Your Feet (21 Years Old)

I’m dying. The gloves, but no jacket? The red plaid button up with a sweater. In Times Square. Why? 😂

My style at 21 was certainly all over the place. It was risk taking. It was willing to try any trend. It felt more for others, than me. At that time, crop tops, skinny jeans, leather jackets, shiny material, prints (florals, stripes, etc.) ALL entered the building. And better believe I wore it all. Hello, Forever 21 and American Eagle. Friends, TV shows, and Pinterest were some of my biggest influences.

At this phase in life, I was ready to hit the bars. I had a solid group of girlfriends, and we’d all get ready together and make our way through a few drinks. Obviously, my faux leather leggings were a staple in my wardrobe. My style at this point (which may arguably be for a lot of people) was centered around external validation. Did my friends like what I was wearing? Did it fit the latest trends? How good do I look?

21 is a weird phase of having some confidence, yet still finding it for yourself fully, rather than seeking it from others.

Mid-Twenties: Refinement and Building Confidence (25 Years Old)

Ahhhhh- this may have been my pivotal point in style.  By 25, I was into my career as a teacher, had just gotten married, and we were expecting out first baby later that year. Bike shorts, animal prints, fringe, ruched tops, overcoats, and neutrals entered the building. And if you know me, you KNOW I love a neutral palette.

Minimizing colors and I still have these shorts, so clearly I was moving in the right direction.

Sidenote: I was the girl at 13 with braces who wouldn’t put color rubber bands on them because I wouldn’t be able to match my outfit daily with them. I cringed at the thought of having hot pink teeth with a blue shirt on. So gray it was- every. single. time. So neutrals, minimal colors- yeah, it’s always been my vibe apparently.

At this point, my style was evolving into more of me. I was beginning to find my own path into what felt good, what I truly liked, while still following trends. The difference was, now, I was more willing to accept that a trend may just not be for me. I was okay with skipping trying out on a thing here or there- my style became a little less risky. Pinterest became my tried-and-true fashion influencer.

I was styling my first baby bump, which was so much fun. I was introducing more matured, business casual attire for work. I was embracing more items that felt like me.

Present Day: Matured, Comfortable, and Unapologetically You

Now, my style is certainly as simple as it gets. I am unwilling to take big time risks, despite how trendy something may be. I’ve learned without trying, what I like, what I don’t, what fits my body well, what doesn’t leave me feeling confident in my own self. And ultimately, that’s my biggest priority now: feeling good in the clothes I’m in. My choice in style is no longer for any external validation. It’s for me. I’m not a big fan of dresses. A skirt isn’t my first choice. I will live in jeans despite the weather outside. Still love a good crop top and bodysuit. And a good pair of boots does the trick.

This is DEFINITELY me. All black + neutrals. A statement piece here and there. And a good pair of boots. Less is more.

I’m in an era of full-on motherhood and entrepreneurship. Practicality has become a major component to my style- although it doesn’t consume it. Especially as a work from home mom, currently pregnant, with three kids under 6, some days are about comfort and survival, others are about simplicity, and others are about being a boss-woman getting shit done. And to do that, sometimes I feel the need to be rocking my trendiest attire. It’s important to embrace changes, especially as our body and lifestyle changes. We only look as good as we feel and feel as good as we look. They’re interchangeable. You can see and feel someone’s confidence. And let’s face it- squeezing into those old pre-baby jeans, now that our hips have widened. Sure, it’s exciting that they fit, but they don’t wear like they used to…just buy a new pair of jeans. You’ll feel a million times better. Embrace the changes.

All our styles have been influenced in some way, at some point in time. Style truly is an evolving journey that changes with us as we grow, as the world grows. And it’s fun to have photos to look back on to see how much of it has evolved with us. Tell me your favorite era of style. What was your most cringe-worthy moment in style? Where are you now?

  1. Aspen Torres says:

    This is so cute! Gives me hope at 22 that one day I’ll stop dressing like Adam Sandler and find things I’m comfortable in & look cute in. 💖

Leave a Reply

Your email address will not be published. Required fields are marked *

Style Evolution: A Look Back from 21 to Now

Style Evolution: A Look Back from 21 to Now

Style Evolution: A Look Back from 21 to Now

Popular Posts

Most business advice hands you generic templates. I help you audit your numbers, pinpoint the exact structural bottleneck holding you back, and engineer a highly simple solution.

Hey, I'm Kait Jensen