Everyday Casual Outfits Then & Now

Hi Friends! Today is special because it’s Doused in Pink’s 10-year birthday! Can you believe that? I created Doused in Pink at the encouragement of my daughter when she was in 7th grade. Boy does time fly; she’s out of college and living on her own now.

My friends always wondered why an introvert who doesn’t like to be the center of attention would put herself out there on the internet. But people have always gravitated to me for fashion advice, help with shopping, and picking out outfits. So, since I was in a style rut myself at the time, I thought it would be a win-win if I could help other women who felt the same way with their everyday casual outfits.

Early on, my blog posts documented what I wore to hold myself accountable for getting dressed daily since I worked from home. From there, I branched from everyday casual outfits to how-to-style, brand partnerships, beauty, DIY, and more.

So, we’re going to celebrate in two ways. First, we will take a trip down memory lane, and I will share my very first blog post: everyday casual outfits and restyle the looks for 2024. And, after that, I have a giveaway for you because I want you to be part of the party too. I thought giving one lucky winner a gift of three of my favorite things would be fun: a Lululemon Belt Bag, a Simply Modern Tumbler, and a pair of Nickel & Suede Earrings. Don’t forget to enter at the end of this post!

Everyday Casual Outfits Then & Now

2014: dark wash denim + tall boots

This photo cracks me up because even my dog Sierra wonders what I’m doing here. The outfit, as a whole, is a classic and still something I would wear today. I tend to keep classic pieces for a long time and recently parted with this sweater when I did my last closet cleanout.

everyday casual winter outfit

2024: ecru denim + Chelsea boots

While the outfit above is timeless, I wear Chelsea boots more often than tall ones now. Instead of dark wash denim, I chose ecru for a winter white look. My monogram necklace is still one of my favorites.

everyday casual winter outfits


2014: infinity scarf + tall boots

Another photo with my feet cut off and my head barely making it in the frame. This button-up was also part of my recent closet purge. Longer layering tanks provided more coverage over leggings and were always something I reached for. The infinity scarf added another layer and additional texture to the look.

everyday casual winter outfit

2024: no scarf + tall boots

I reworked this outfit with a longer, oversized chambray button-up. The vest and hat are the same. I finally had to say goodbye to my Sam Edelman Penny Boots and opted for a black suede pair for this reworked look. Which styling do you prefer? 2014 or 2024?

everyday casual winter outfits


2014: pink + camo

Don’t mind the blurry photo. I’ve always loved the pink and olive green color combo because it works unexpectedly. Camouflage print was a huge trend in the 2010s. It was such a great neutral that could be mixed and matched with almost anything. The print seems to have retired for now, but I’m certain it will reemerge at some point.

everyday casual outfit

2024: pink + olive

I’ve packed away my camo jeans for now but still wear the pink and olive color combination frequently. To update the look, I opted for wide-leg olive green pants, a pink sweater, and neutral booties.

everyday casual outfits


2014: infinity scarf + Hunter boots

I never really feel like I’m aging until I look back at photos. Are you the same way? Also, I’m unsure why my daughter and I thought this was a cool angle. Anyway, it’s another classic look I would style just a little differently today.

everyday casual outfit

2024: silk scarf + suede boots

I choose a silk scarf and an oversized cardigan to modernize this outfit. And since I seem only to wear my Hunter boots now when I’m doing yard work, I opted for a black suede boot to keep with the vibe.

everyday casual winter outfits


2014: infinity scarf + tall boots

A button-down shirt, distressed denim, and tall boots were one of my go-to looks in 2014. This outfit is cute and has a fun vibe, but my style has changed over the past ten years, and you’ll see in the next photo how I’m styling the same shirt today. Do you spy the remnants of my daughter’s 13th birthday party in the background?

everyday casual winter outfit

2024: open front + Chelsea boots

Yep, the exact shirt is still hanging in my closet. I wore the flannel open over a tank top to remake the look and went for non-distressed denim and Chelsea boots.

everyday casual outfits

That’s a wrap! I hope you enjoyed taking a look back at my first everyday casual outfits post. Which outfit transformation is your favorite? Let me know in the comments! And don’t forget to enter my giveaway and link up with Kellyann and me below!


I’m giving away a Lululemon Everywhere Belt Bag in Flush Pink, Simply Modern Tumbler in Sea Glass, and Nickel & Suede Lagoon Esti Earrings to celebrate ten years of blogging. Enter through the Rafflecopter below. The giveaway will run for two weeks, and the winner will be announced in my newsletter on March 5th.

a Rafflecopter giveaway

Also see: How to Make a Basic Everyday Outfit Not Look Basic and Green Utility Jacket Outfit

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Linking up with:

Away from the Blue  | Fine Whatever Blog | Between Naps on the Porch | I do de Claire

Elegantly Dressed and Stylish | Walking in Memphis in High Heels & The Fashion Canvas

The Style Splash | Is This Mutton? | Curated by Jennifer

Mummabstylish | Shelbee On the Edge | Nancy’s Fashion Style

Momfessionals | Marsha in the Middle | Sunday Showcase

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Meet Jill

Thanks for visiting Doused in Pink, a Chicago style blog. I am here to bring simple style tips and outfit inspiration to help you elevate your everyday style. You will also find posts on the best beauty products, wellness, DIY projects and decorating ideas. My goal is that you leave feeling like you learned something new that helps you feel confident when you walk out the door.

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