My Style Evolution from 2016 to 2026
The 2016 trend is taking over social media, and I thought it’d be fun to look back at what I was wearing in 2016 and reflect on how my style has changed since then! Like you, I also can’t believe 2016 was a full 10 years ago. 2016 marked my last first day of school; I can’t believe I graduated with my PhD just about nine years ago.
By far the majority of my blog posts on CCCH back in 2016 were outfit posts. It was a lot easier to photograph my outfits regularly when I was a grad student and not a full-time employee. I’d like to get back into it, but my style these days is kind of boring compared to what I used to share. 😆
Join me on this journey down memory lane, and share how your style has changed since 2016 in the comments!
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My Style Evolution from 2016 to 2026
First off, I have to say that it’s fun I’ve been blogging for so long because I have so much of my style documented! Of course, not all of my outfits were home runs—some are downright cringy now—but it’s fun to look back and laugh now. Or maybe shudder because some of the things we used to wear 10 years ago are coming back in style.
Below, I selected an outfit from each month of 2016 and shared why I would (or would not) wear the outfit in 2026, or how I might modify it to fit my style 10 years later. Click on each outfit photo to be taken to the original blog post!
January 2016
February 2016
Let’s kick things off at the start of 2016. I put a lot more effort into my winter outfits in 2016 than I do now. I’d rather wear pretty much anything else other than a skirt with tights now, haha! (I am wearing fleece leggings here, which really do make all the difference.)
The outfit from February is a Pinterest-favorite and has always been a favorite of mine even though it’s not really my style anymore. I’ll always love a blush pink and burgundy color combination. I still own the boots!
March 2016
April 2016
In 2016, I really loved to wear a third piece to finish my outfits (or maybe even a fourth piece, as seen in my April outfit). That hasn’t changed in 2026! Third pieces really do make outfits feel more complete and intentional. A shirt + jeans + ankle boots + jacket was a go-to outfit formula for me.
While I wouldn’t probably wear my April outfit again, I don’t hate it. There’s a lot going on texturally, but that was the look I was going for. It’s been a long time since I really played around with my outfits like this! I want to see what this would look like with slim black boots so no skin showed.
May 2016
June 2016
I loved my dark floral skirt so much and was so sad when I couldn’t fit into it anymore! This wasn’t the most exciting outfit I put together with it, but I loved my ankle boots a lot and enjoyed pairing them with short skirts when I was a grad student.
The June outfit is a dress that has the illusion of being two pieces (a cropped top over a high-waisted skirt). I didn’t wear it much, but this is still one of my favorite looks from summer 2016. It’s nautical and preppy! I still own everything except for the dress, though my gold sandals are way more beat up now after taking them on multiple beach vacations.
July 2016
August 2016
In summer 2016, I wore a lot of dresses, skirts, and shorts; in 2026 (once it warms up), like in 2025, you can find me mostly in shorts. I currently only own one skirt that fits me, and it’s a midi. I also wear a black dress frequently, but it’s also a midi. Haha! The mini length to midi length was one major shift in my wardrobe.
The August outfit is still one of my favorites, and I’d totally wear something similar in 2026. I remember being in awe that my black silk top and black silk shorts worked together so seamlessly (they were from different brands, so I wasn’t totally convinced it’d work out). I’m not big into rompers or jumpsuits, so the “faux” version is perfect!
September 2016
October 2016
Denim skirts are back in style (or did they ever really go out of style?), so it’d be fun to recreate the September outfit now. The more I look at this outfit, the more I think I’d wear it again now. The downside to denim skirts is the lack of stretch! I used to own (and wear) a lot of clothes with minimal stretch, and I don’t own those pieces anymore for a reason (lack of stretch is not comfortable).
Another outfit, another midi skirt with flat shoes. I still love a sweater + shorts or short skirt combination, though like I said, I pretty much only wear shorts now if I’m not wearing jeans or pants. I still own these black loafers, which have been in my wardrobe since April 2014!
November 2016
December 2016
I’m less likely to wear skinny ponte pants now that wide leg pants are more in style, but gosh, I loved these pants sooo much! They were a grad school wardrobe workhorse. The layering in this outfit is fun and reminds me to play around with my outfits again. I don’t really own any fun layering pieces anymore.
Wearing a mini skirt and rain boots in the snow is not something I’d wear in 2026, but I’m glad 2016 me had fun! (I remember freezing during this shoot.) Nowadays, I’d swap out the skirt for leggings and the boots for something that’s actually insulated. 😆