What Was I Wearing 10 Years Ago?

November 18, 2025

I thought it would be fun to do something a little different today. On Instagram, I’ve seen bloggers share old outfits that they wouldn’t wear anymore and how they would change them. So, let’s try that for a change of pace. Here are three outfits I actually wore in November 2015. For each, I’ll tell you what I think still works and what I would update. I’d also love to hear your thoughts!

Look 1 (left to right): Not a horrible look. Of course the distressed skinny jeans definitely look dated. And the huge oversized blanket scarf is a trend long passed it’s “use by” date. But I actually STILL have that plain beige sweater (similar). I’m pretty sure it’s the same one! (Good basics really don’t go out of style, do they?) I don’t have the red suede loafers anymore, but I still think they would totally work. To change the look, I would wear wide leg jeans or kick flares and a more normal sized scarf or some other accessory instead.

Look 2: Honestly, head to toe, I think I could pull off this look today. Again, I’d say replacing the skinny jeans with wide legs or kick flares would definitely make it look more 2025, but the classic dark wash skinny jeans don’t look AS dated as the distressed skinny jeans, do they? I feel like the puffer vest went from a trend to a classic, so I think it basically still works. A black and white striped sweater and little black ankle booties both work forever!

Look 3: Does anyone remember the trend of skinny black jeans with the knees busting out! It was totally a look. But it’s definitely not in anymore. The jeans would definitely need to be updated to wide leg or kick flares, with no holes. I have had a black turtleneck as a key part of my wardrobe for decades! And it’s never really been very different and it always looks great in my opinion. The leopard heels look timeless to me, but it does make me realize how much I prioritize comfort as I’ve gotten older. I’d probably go with a lower heel for sure. The bag also looks out of style. I remember this was a dupe of a Chloe Drew bag that was having a big moment. I’ve learned over the years to not buy dupes (I feel like a phony wearing them) and also not to get anything that is very IN right at the moment. If it’s super popular and very trendy, it will no doubt look wrong very soon. Too bad, but true, right? (Of course if I had an unlimited clothing budget, then hey, why not? But I don’t!) When I did treat myself to a real designer bag, I went with this classic one.

And what’s with the red hair in the middle picture? It was just a temporary rinse. Remember when playing around with those was popular?

Want to share what you were wearing ten years ago? And/or make some comments on these looks? We’d love to hear it!

If you’re looking for some up-to-date fashion, there is plenty on the blog right now. Check out my new Quince pieces, my new Charlie B pieces, and some cozy and comfy new boots.

Fun & Fashion,

Dawn Lucy

About the blog: Fashion Should Be Fun is me talking to you, other middle aged women like me who are over 40, but not over fashion.  We still want to look beautiful and stylish.  We still want to have fun with trends.  And we don’t need anyone giving us rules, because we’re all different. We all have our own shapes and bodies, parts we’d like to cover and parts we still don’t mind showing off a bit.  This is a place for me to share my love of fashion with you, style ideas, tips, trends, and inspiration. I know how liking the way we look can translate into confidence and energy. I know we have so much life left to live and so much adventure ahead of us. Let’s show the world you’re never too old to have fun and be fierce!

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