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How To Get Out Of A Style Rut Challenge

Let’s be honest, style ruts happen to the best of us. It’s the reason you hear “I have nothing to wear” when in all reality, we have a closet full of clothing. And I bet each and every one of us could benefit from a challenge like this.
It all started when my friend, Tresi, reached out with the idea about how to get out of a style rut. It was an idea made in heaven and I was all in.

Quote of the day: “Our potential is one thing. What we do with it is quite another.” Angela Duckworth

Even if you are someone who loves her style and thinks you dress just “fine”, I have shared more than one article about how changing it up can be helpful.
There was the time when my crew visited each other’s closets and put together outfits. This is ideal because there’s no Money spent, yet you get different ideas of how to wear what you already have.

Then there was the time that I let my hubby choose my outfit.
We also toodled over to Goodwill and put together an outfit for each other.

While you can certainly challenge yourself as Tresi and I did in this example, having a friend join in can give you options you never thought about.

I’ll share both Tresi’s and my challenge for how to get out of a style rut first, then ideas of how to incorporate this challenge for your own closet.

AND YES, you should try this. You have nothing to lose and a ton to gain.


Meet Tresi

It all started when Tresi emailed me asking: “Do you find that you get a crush on a colour or style? I do! Once that happens, I get stuck.”

After that email, I asked her if she would like to join me on a challenge of how to get out of a style rut. Below is Tresi’s commentary in italics.

I’ve been in a rut lately with the over 50s uniform as recommended by many fashion bloggers (the striped tee, blue jeans, and white sneakers). I feel like it used to look so fresh and chic, but I’m bored with it now. When I’m out and about, I see so many similar iterations, including the men’s version with polo shirt, that I feel compliant and conforming, which is not me at all.
I decided to focus on the striped T shirt, as I’ve got loads and any of these ideas can be transferred to other outfits.

I’ve tried tucking the shirt, but after my hip operation, I’ve lost an inch between my waist and hips, which makes my proportions off with waist jeans; it’s better if I have high waisted jeans, but I don’t find those so comfortable.

I still wanted the convenience and comfort of the original outfit, so I decided to describe my outfit to myself, but without any reference to colour, to see what popped out from the wardrobe.
Surprising how when I swapped out sneakers to blue instead of white, it changed the outfit so much.

I will say that I Love how Tresi cuffed the brown jeans. To me, that adds a lot to the look, also.

Future idea: I think I’d add my long, button through denim dress as a duster to make it more interesting. (ooh, and maybe tan boots with blue socks on chilly days)

Wear The Striped Top Over Your Shoulders

How It Progressed

So now that I’d climbed out of the rut, I wanted to use the top as a totally different garment. To be honest, this dress was on the reject pile, but the colour is lovely so I tried wearing the striped tee over my shoulders.

I really liked the end result. The leggings make the front splits less of a feature, and cuffing them works for me. The print mixing definitely wakes up the outfit, and adds warmth, without too much bulk, still spring-like, and draws the eye upwards-always a good thing!
The sandals pick up the orange in the flower print and looked more on trend than trainers did to my eye (plus they’re new and I wanted to wear them!)

Dress Under Jumper Dress

My Style Rut Challenge

When I wore this white and rust dress for one of my Daily outfits (seen on Monday), I noticed that I always style it with turquoise. While this daily outfit is unusual in that I layered 2 dresses together, I still wanted to use it for my how to get out of a style rut challenge.

So I decided to try 2 different color schemes with the dress and embrace a bit of matching (one of the things that I’m usually trying to get away from).
On the left, I wore a brown leather belt to match the stripe in the dress, and then blue shoes and jewelry.

On the right, I wore a white vest to match the background of the dress and green sneakers.

I know that the big thing is that “dresses are a one-and-done outfit,” which makes them easy to style. But that doesn’t mean that’s the only way to wear them, right? That’s another style rut that most of us fall into.


How It Progressed

So these photos are ways to style the dress in a whole different category.
On the left, I added my polka dot skirt over it (allowing a bit of the dress to show with the ruching).
This is an easy way to transform a dress into a top.

With certain dresses, there is another way.
On the right, I tried tucking some of the dress material up under the elastic waistband. Because the dress material is thin, this worked better than I imagined.
BTW, I’ve done the same thing with this striped dress (see the fourth option) as well as with a long tunic by knotting it.

Style tip: Just because a clothing item is sold one way, doesn’t mean there aren’t other ways you can wear it.
I talk about this many times because it’s creative and fun.
Want to see this with another dress?
Or I’ve worn a short skirt as a top.
And then there was the time I rearranged this long sleeve shirt to make it good for summer.

Now let’s talk about how you can apply this struggle of how to get out of a style rut for yourself.

1. Shop Your Closet Differently

The best part of this challenge is that neither of us bought anything new. Instead, Tresi pulled her striped top out of the closet and said, “Let’s make this interesting.” The one thing that really stood out to me is how she “decided to describe my outfit to myself, but without any reference to colour” and how that changed the next outfit.

Since I had recently caught myself pairing turquoise with my dress, I knew I had to try something else. Which then led to multiple ways to reimagine my dress.

Style Tip: Next time you feel stuck, pick one piece from your closet (like a top, blazer, or even a scarf) and commit to styling it five completely different ways throughout the week. Another idea is to ask yourself what you would normally wear with the item, and then make sure to try something very different.


2. Embrace Color and Contrast

This challenge was about breaking your normal mold—because let’s be real, we often fall into the trap of pairing either the same colors together or the same pieces.

I feel like color is the easiest thing to change in an outfit and can be very powerful.

Style Tip: Try combining an item from your closet with three unexpected colors. Use accessories, shoes, or even lipstick to inject personality into the look. Start small if you’re color-shy—maybe it’s just a bright shoe or a bold necklace—but let yourself play!
Remember how I did this with my colorful sneakers recently.


3. Add Layers with Purpose

Both of us found success in layering—but not just for warmth! Layering adds visual interest, dimension, and creativity to any outfit.

Layering allows you to transform the silhouette and vibe of a look completely. You can add other style genres to a piece when you add other items.

Style Tip: Play with proportions when layering. Try a long cardigan over a shorter dress, or a cropped jacket over a flowy maxi. Even a belt can act as a layering piece when styled intentionally!


4. Use Accessories as Wildcards

Another secret to getting out of a style rut? Accessories! We both incorporated belts, scarves, statement jewelry, and fun shoes to change the energy of our original outfit.

Accessories let you flirt with different aesthetics without changing your base wardrobe.

Style Tip: Choose three accessories you don’t wear often and put them in your “outfit rotation” for a week. Whether it’s a wide belt, a beret, or a chunky necklace, commit to using it in at least two outfits. Accessories can reignite your style spark like nothing else.


5. Let Go of “Rules”

Sometimes I think that when we get in a style rut, it could be because we are trying to follow too many rules. Even just the thought that our outfits have to be flattering can be very limiting. Let yourself have fun and put together items that you would never think to style before.

The best part is that if you don’t like it, there’s no risk. You didn’t waste money or even time because the time playing in your closet is well spent. It’s much better for your brain Health than sitting and watching tv.

Let yourself experiment without the fear of “getting it wrong.” That’s where the style magic lives.

Style Tip: Try breaking one “fashion rule” this week. Make sure it’s one that you always follow and try being a rebel. Even if it’s just wearing the outfit around the house–that counts. The more you play, the more confidence you’ll build.


6. Document the Journey

One thing I always encourage? Take photos of your outfits, especially when you’re doing a style challenge. It not only helps you see what works and what doesn’t, but it also gives you a visual diary of your creativity in action.

Plus, it’s so much easier to spot patterns (and ruts!) when you can look back and evaluate. It’s like your own personal Pinterest board, curated just for you.

Style tip: Cameras allow you to see your looks with a different lens than the mirror. I’ve shared an easy way to take selfies without having to hold your camera.


Final Thoughts: Get Curious, Not Critical

At the end of the day, how to get out of a style rut isn’t about buying a new wardrobe or following the latest trend.
It’s about getting curious about what you already own and rediscovering your style joy. I think both Tresi and I had fun by challenging ourselves to think differently this way.

So next time you feel stuck, pick one item and say, “How would Tresi or Jodie wear this?”
Use it as your starting point for play and self-expression.

Remember, fashion isn’t about perfection—it’s about progress and personality.

As much as I love my site, Jodie’s Touch of Style, I really enjoy putting together my daily emails. I consider my emails an extension of my blog that is chocked full of positive inspiration that one friend calls a “Variety Show.”
I include articles, videos and posts that strike my fancy and since I have no siblings to share with, I share with you.

How To Get Out Of A Style Rut With 2 Women

How To Get Out Of A Style Rut Challenge &Raquo; Tutke

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The post How To Get Out Of A Style Rut Challenge appeared first on Jodie’s Touch of Style.

Jodie's Touch of Style showcases how it's never too late to look great including other older women and myself talking about fashion, beauty, and lifestyle issues.

As a retired dentist, Jodie takes her love of clothing and shopping and has come to find her superpowers in styling the same item in many ways. She is also a huge advocate for embracing our age and bodies. Getting old is a wonderful thing and learning to love ourselves while it happens is very freeing.

Looking great can happen no matter what age, shape or budget, as we show on Jodie's Touch of Style.

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