5 Years Later: Shades of Autumn

How to style a faux leather jacket for fall | casual fall outfit idea | Cotton Cashmere Cat Hair

Every month this year, I’m picking an outfit that I first wore and blogged back in 2016 (a whole five years ago, if you can believe it!) and recreating it using the same (or very similar) pieces! I actually could have started this series in 2020 or even 2019, but 2016 is the first full year I used a DSLR for blog photos, and no one needs to be reminded of the photos I took with the camera prior to that (lol).

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 rewear your favorite outfits/items!

I had a hard time deciding between two outfits for this month, so I polled you on Instagram and most people liked this outfit the best! I’ll be honest: I was sure I was going to go with the other outfit (Tropical storm) because not everything in the original Shades of autumn outfit still fit me, but I made it work and am pleased with the result. Let’s dive into the next 5 years later outfit of fall!

Whipstitch floppy hat fall outfit idea | leather jacket outfit | Cotton Cashmere Cat Hair
Blank NYC Life Changer moto jacket + Everlane authentic stretch skinny jeans casual fall outfit idea | Cotton Cashmere Cat Hair
Madewell green plaid flannel shirt outfit | how to style a flannel shirt for fall | Cotton Cashmere Cat Hair

SHADES OF AUTUMN — 2021 vs. 2016

The original Shades of autumn outfit was one of my favorites from fall 2016. I loved the combination of the green plaid flannel and the tawny brown floppy hat and how it was all grounded by the black on bottom. I wore my J.Crew Pixie pants to (near) death; I had to get them reinforced in the crotch by a tailor! I still own them all these years later even though they don’t fit quite as well as they used to haha. In 2016, I wore a Madewell shirt, J.Crew pants, Sam Edelman boots, and Phase 3 hat via Nordstrom. I still own everything from this outfit and included three of the four items in the new 2021 version. I also added another layer!

I looove this green plaid flannel shirt from Madewell. I purchased it in summer 2016 and have adored it ever since! I first purchased it in a size XS, and then after it shrunk in the wash, I sold that one and purchased a new shirt in size small. Now I’m wishing I had a medium! Ha. #broadshoulderproblems I am keeping my eyes peeled for a good (second) replacement on Poshmark, lol. It’s not too often that you find a good green and black plaid—a lot of the plaid flannel shirts you’ll find are green and blue/navy. That’s why I’ve kept this one around after all these years!

I’ve owned the Sam Edelman Petty ankle boots for years as well! I received them as a gift back in fall 2014 (!!! a year after I started my blog), and not surprisingly, they’re one of the most worn items in my whole closet. Do you remember when these boots were EVERYWHERE? I swear they were the only boots you’d see on the FemaleFashionAdvice subreddit, of which I lurked often back in the day (and I’m pretty sure that’s how I found out about them in the first place). I have multiple pairs of black ankle boots now, all slightly different from each other. I love these for their inside zippers, low heel, and solid black color. They’ve held up well over the years!

My Phase 3 whipstitch floppy hat was a Nordstrom Anniversary Sale purchase many years ago and ended up being one of the best. The whipstitch is a fun addition that reminds me of Woody’s cowboy hat in Toy Story. The color is most true to my 2021 outfit photos—it’s funny how much my photo editing style has changed since 2016 but I do think it’s much better now! I guess we’ll see what it looks like 5 years from now. I don’t shy away from wearing brown and black together, especially when it’s cognac brown and black. The contrast is my favorite!

Tawny brown floppy hat + green plaid flannel shirt | colorful fall outfit idea | Cotton Cashmere Cat Hair
Everlane black authentic stretch skinny jeans | how to style black denim for fall | Cotton Cashmere Cat Hair

Even though I still own the ponte pants I wore in the original 2016 outfit, they don’t fit quite as well as they used to, so I opted instead for my pair of black jeans. The outfit felt unfinished without some sort of top layer, so I tried a few on before leaving the house and stuck with the classic leather jacket.

I’m wearing the authentic stretch high-rise skinny jeans in black from Everlane. I figured they would fit and feel more comfortable than the ponte pants, but…they really weren’t. Lol. They felt small. I think one of my next purchases will be a new pair of curvy authentic stretch high-rise skinny jeans in black! My current pair is the “regular”/non-curvy style, and I really don’t know if I’m ever going to go back to that. The curvy fit is a game changer. Also, my jeans are not as stark black as they used to be. They definitely need to be dyed to get that deep black color back. I’m planning to write an update on my Everlane denim soon so keep an eye out!

This outfit felt too plain as it was originally, so I threw on my Life Changer faux leather moto jacket! I did try on other options, but this one just worked the best with the overall vibe. Can’t ever go wrong with a leather jacket. It adds just the right amount of edge to any of my outfits and definitely always makes me feel cooler than I actually am. Impostor syndrome who?

What’s the verdict? Are you a fan of the new 2021 version or do you prefer the 2016 original? While I love the ponte pants in the original outfit, I’m loving the updated version with the jeans and jacket!

Browse all outfits in the 5 years later series!


OUTFIT DETAILS

BlankNYC jacket / exact in plus sizes or similar (last seen here)
Madewell shirt / old; similar by Old Navy or Amazon
Everlane jeans / exact (curvy style) (review here)
Sam Edelman boots / old; similar from Nordstrom Rack or Amazon
Phase 3 hat / old; similar from Nordstrom (last seen here) Le Specs sunglasses / exact via Shopbop, Nordstrom, or Net-A-Porter
Dior Lip Glow in rosewood / exact