5 Years Later: Freak Alley

5 years later outfit challenge: Freak Alley, downtown Boise, Idaho | Cotton Cashmere Cat Hair

Last year, I started doing the 5 years later outfit challenge: I picked out an outfit I first wore and blogged back in 2016 and recreated it using the same (or very similar) items. I had so much fun that I decided to keep it going for 2022, so now I’m recreating outfits I wore back in 2017! (Wow, I can’t believe 2017 was 5 years ago already…that was the year I finished my PhD!)

My goals with this series are to put together updated versions of some of my favorite past outfits, see how much my style has changed over the years (if at all), highlight the items that are still in my closet five or more years later, determine if it’s time to pass on some of my older items, inspire you to evaluate the longevity in your own wardrobe, and most importantly, remind you (and myself) that it’s cool to re-wear your favorite outfits/items!

Let’s discuss the first 5 years later outfit of fall 2022!

Casual fall style with Madewell demi-boot jeans | Cotton Cashmere Cat Hair
How to style the Madewell oversized shirt jacket for fall | Cotton Cashmere Cat Hair
Celebrating my 33rd birthday at Freak Alley in downtown Boise | Cotton Cashmere Cat Hair

Freak Alley — 2022 vs. 2017

We photographed the original Freak Alley outfit in Freak Alley, which is a collection of public art on the buildings in an alleyway between 8th and 9th (streets to the east and west) and Idaho and Bannock (streets to the south and north) in downtown Boise. It’s a popular place to hang out, check out the art (which changes periodically), and take photos! One of my younger brothers had his grad photos taken here. I would’ve taken these photos of the new outfit in front of the Breaking Boise art again had there not been a car in the way (this particular area is also a parking lot). It’s still there 5 years later! (Though Aaron Paul is selling his Boise house.)

I wore this outfit on my 33rd birthday last Friday! We quickly shot these photos before going out to Happy Hour and dinner with my parents (all four of them!) and Korri’s parents. It took forever because the lighting wasn’t great for the DSLR camera, so we took some photos with the camera and some with Korri’s new iPhone 14 Pro Max. Can you tell which photos were taken with which camera? 😏 In 2017, I wore a BlankNYC faux leather jacket, Madewell flannel shirt, Madewell skinny jeans, and Earth ankle boots. I still own three of the four items but included only one in the new look for 2022!

Items from 2017 I’m Still Wearing in 2022

The only item from the 2017 outfit that I’m wearing in the new 2022 outfit is my pair of black velvet ankle boots. I received them courtesy of Earth Brands and still love them! Earth makes some of the most comfortable shoes. These boots get a lot of wear in the fall and winter because of the velvet texture. They work really well for more formal settings, like the ballet. I know this style of ankle boot isn’t exactly in style anymore but I cannot afford to replace my whole wardrobe, nor do I want to!

Even though I’m not wearing them here, I still own the BlankNYC faux leather jacket and Madewell flannel shirt. I still wear the leather jacket regularly in the fall and spring (I wore it out to lunch on Saturday!), but it’s not the oversized fit that is in now. I actually can’t layer much with it. The flannel shirt doesn’t get as much wear; the flannel itself is thin and I gravitate towards my warmer, thicker flannels. I still love the green plaid! I decided to go in a completely different direction for this outfit and opted instead for a green corduroy shirt jacket.

Downtown Boise casual fall outfit idea with corduroy shirt jacket | Cotton Cashmere Cat Hair
Casual fall style in Freak Alley, downtown Boise | Cotton Cashmere Cat Hair

What’s New in 2022

The remaining four items (plus the sunglasses) in the 2022 version are new! I’ve not been challenging myself to completely restyle most of my 5 years later outfits so far and really decided to challenge myself this time. I actually had a lot of fun changing up this look!

I don’t own the skinny jeans I wore in the 2017 outfit anymore, and I actually don’t really have a pair of dark wash skinny jeans that fit me right now. These demi-boot jeans are really the only dark wash denim I own and fit into now. I really like how they look with the ankle boots; the length of the jeans works well with the height of the ankle boots and shows that little sliver of skin that I like on me (helps to not make the outfit feel so weighed down). Plus, that slight flare is more on-trend than skinny jeans so it worked out. 😉

I mentioned above that I do still own the flannel shirt and leather jacket I wore in 2017, but I decided to go in a different direction this time. I picked a basic black tank top and layered an oversized corduroy shirt jacket. This one by Madewell is a recent addition to my wardrobe, and I’m loving it! It’s so cozy. It is designed to be oversized, but I might’ve gotten away with a size XS (I’m wearing a small here; I have broad shoulders and prefer things to fit too big rather than too small because of that). The dark green is so pretty! This update really brings the whole outfit into 2022 even though my ankle boots might be considered dated.

On the accessories front, I added a belt because the outfit felt unfinished without it, and I also put on a simple pair of stud earrings. Korri got me the fun Birthday Girl headband; I saw a lady wearing a similar one when we were out to dinner earlier in the week and had commented on it!

Which outfit is more your style: the 2017 original with the leather jacket and skinny jeans or the new 2022 version with the shirt jacket and demi-boot jeans? I enjoyed totally rethinking this outfit!

Browse all outfits in the 5 years later series!


OUTFIT DETAILS

Madewell shirt jacket / exact (also available from Nordstrom)
Everlane top / old; similar or similar (cropped)
Madewell jeans / old; shop all demi-boot jeans or similar by Old Navy
Earth boots c/o / old; similar by Bella Vita or Dr. Scholl's (last seen here)
Madewell belt / old; similar or similar
Maison Miru earrings / exact or similar from Nordstrom Rack
Le Specs sunglasses / exact via Revolve, Shopbop, or Nordstrom
Dior Lip Glow in rosewood / exact
Amazon headband / exact