What I Wore Then vs. What I Wore Now

One of my favorite series on Instagram is my “What I Wore Then vs. What I Wore Now” posts. These posts are so fun for me to put together because they encourage me to get creative and rework some of my older outfits to show how I’d style them with pieces from my current closet. It’s been a while since I last shared these in a blog post, so today, I thought I’d round up some of my most recent updates.

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The goal of my What I Wore Then vs. Now Posts

My “What I Wore Then vs. Now” update posts always get a lot of attention. I’d say most people really enjoy them and find them helpful, but there are always a few critics who think the older outfit looks better or feel that I’m implying they need to buy a whole new wardrobe.

Let me be clear—I love the original outfits I’m sharing. I styled them, and I’d often still wear them today! However, my wardrobe has evolved over 11 years of blogging. I’ve replaced staples, tried new trends and styles, and learned a lot about dressing my body, especially after having two babies. I always aim to honor the old outfit while giving it a modern makeover.

My goal with these “What I Wore Then vs. Now” updates is to make newer trends feel less intimidating. With all the conflicting fashion advice on social media, it’s easy to feel overwhelmed when exploring new styles—especially for millennial women like myself, who don’t want to dress too old but also don’t want to dress like a teenager. I want women to feel encouraged to try new trends without losing their personal style or those classic outfit combinations they’ve always loved.

So today, let’s take a closer look at some of the recent outfit updates I have made.

Outfit 1: Colored Skinny Jeans Update

I wore this first outfit back in April 2014. I remember loving these red jeans that I bought on clearance at Kohl’s. They fit me great, and I always felt amazing wearing them. I paired them with a basic black-and-white striped top and my favorite LC Lauren Conrad blazer at the time. For shoes, I wore my Old Navy ballet flats, also a clearance find.

To update the outfit, I swapped out the skinny jeans for my berry wide-leg cropped pants from my fall capsule wardrobe. While I always loved those red skinny jeans, they had a very low rise, and I let them go years ago after I had Jack.

These days, I usually go for cropped wide-leg pants when wearing colored bottoms. For the top, I grabbed another basic striped shirt, similar to the original. I’m not sure what happened to that first striped top, but it probably wore out over time. I updated my black blazer a few years back with this thrifted one, which I like better than the original. While I still mix patterns now and then, I chose these black-toe sling-back shoes for a more polished look with this outfit.

Outfit Details HERE!

Outfit 2: Maxi Skirt Update

I wore this outfit in March 2015. I was a huge fan of these comfortable cotton maxi skirts, and I believe this navy one was a find from Ross Dress for Less. Pairing a long tank top and denim jacket with them, as I did here, was a go-to look for me!

The issue with long maxi skirts is that they don’t have much shape, and I also didn’t love how long they were. Now, if I’m going to wear a longer skirt, I prefer it a bit shorter. That’s why I decided to update this look with this champagne-colored silk slip skirt. These skirts are pretty popular right now, and I like that they have a bit more shape compared to the long maxi.

To keep a similar color scheme, I went with a navy top. Instead of a statement necklace, I added a pop of color with my bracelets and used a belt to break up the outfit. To complete the look, I opted for a more oversized denim jacket; I felt the lighter color balanced out the darker shirt.

People on Instagram didn’t seem to like my denim jacket choice, but I still do. If I were to style this again, I might go with a more fitted denim jacket, like my ABLE jacket. As for shoes, I wore either flats or sandals in the first look, so I went with my gold flats this time. I’ve always loved ballet flats.

Outfit details HERE!

Outfit 3: Blazer and Jeans Update

I wore this look back in November 2014. I’ve always loved pairing blazers with jeans. This gray blazer was from the LC Lauren Conrad line at Kohl’s, and I believe I bought it on clearance. The jeans were also a clearance find. One thing I remember about my jeans during this time was that I was always looking for a bargain, so the fit was often a little off—a mistake I avoid now. My shoes were Tory Burch look-alike flats that I found on clearance at DSW, and I wore them all the time!

To update this look, I decided to swap out the gray blazer for something with more color and pattern. I found the black-and-gray combo a bit dull, so this houndstooth blazer is the perfect way to brighten it up. I also replaced the low-rise skinny jeans with high-rise kick-flare jeans, one of my favorite styles. They maintain a slim fit through the thighs but flare out at the ankle.

For accessories, I replaced the long beaded necklace with lighter jewelry and added a belt to define my waist and break up the outfit. For shoes, these quilted black-toe ballet flats are a great upgrade from my old faux Tory Burch flats.

Outfit details HERE!

Outfit 4: Cardigan and Black Pants Update

I wore this outfit to work in August 2014, and I remember loving it. The polka-dot blouse was from Meijer, where I did my grocery shopping. The pants were a pair of Jessica Simpson black jeggings I bought at TJMaxx, and I wore them at least once or twice a week. The wedge shoes were from Target; I was obsessed with Kate Middleton’s style at the time, and she often wore cute closed-toe wedges, so I had to have a pair. Unfortunately, my Target shoes weren’t very comfortable and slipped off my feet often.

To update this look, I decided to keep the black-and-white pattern in my outfit, but this time, I put it into my cardigan by choosing this striped lady jacket. I layered it over a white ribbed crew-neck T-shirt. For my pants, I swapped the jeggings for a high-waisted pair of slim, straight-leg jeans.

For accessories, I went with a belt instead of a long necklace. The belt adds detail to the outfit similar to the long necklace but draws attention to my waist, which I like. I kept my jewelry simple with my usual gold pieces. The biggest update to this outfit was the shoes; these are much more comfortable than the original pair. They have a small block heel, making them perfect for wearing to work.

Outfit details HERE!

I do really enjoy putting together these what I wore then vs. now posts, so you can look for more soon! I plan to do some holiday updating posts soon, so look for those over on my Instagram and LTK pages!