5 Years Later: On Faking Confidence

Casual workwear summer outfit idea with tropical-print silk shirt and Madewell light wash skinny jeans | 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!

Let’s discuss the final 5 years later outfit of summer!

How to style a tropical-print silk shirt | casual workwear outfit idea | Cotton Cashmere Cat Hair
Casual workwear outfit idea | what to wear on casual Friday in the office | Cotton Cashmere Cat Hair
Amour Vert tropical-print shirt casual warm weather outfit for the office | colorful summer outfit idea | Cotton Cashmere Cat Hair

ON FAKING CONFIDENCE — 2021 vs. 2016

I constantly struggle with imposter syndrome. I guess I thought at some point it would magically disappear, but that hasn’t happened yet, LOL. Five years ago, I wrote about how wearing just the right outfit makes me come off as more confident than I actually am and sort of tricks myself into feeling more confident. That was the topic of my “On faking confidence" outfit post that I recreated here. In 2016, I wore an Amour Vert shirt, Madewell jeans, J.Crew flats, and Madewell earrings. I still own three of the original four items and included two of them in the new 2021 version.

I purchased the tropical-print silk shirt from Amour Vert five years ago, a month before I wore the original outfit. At the time, I was debating between this shirt and a blue patterned wrap dress. I went with the shirt because I figured I’d get more wear out of it—and I absolutely made the right decision! I still love it five years later. It was a HUGE ($$$) purchase for me at the time, too, since I was still in grad school. I still baby it because it’s silk, but it has held up so well…probably because I haven’t worn it all that much, haha. I got sriracha on it the other day and I dabbed it with water and now have no idea where the original stain was?! Whew! Haha. It’s also my go-to for any sort of tropical-themed get-together (just had one of these recently to send my cousin off to get her PhD in Hawaii!).

The J.Crew metallic gold Gemma flats are one of the oldest pairs of shoes in my closet! I purchased them in winter 2016, and they’ve been a fun addition to my wardrobe ever since then. I own two pairs of the cult-favorite J.Crew Cece flats, which I found fit me best in a half size up from my usual, and I stuck with my true size in these flats. I will admit that I don’t wear them all that often because the seam running along the top of the shoe feels like it’s going to give me blisters, and I try to avoid those at all cost. It could also just be that my feet are NOT used to wearing flats after over a year of working from home + not wearing flats so far this summer! To be honest, it’s been probably a good two years since I wore flats out of the house for any significant length of time. Crazy.

Gold pointed flat casual workwear summer outfit idea | Madewell medium Transport tote | Cotton Cashmere Cat Hair
How to style skinny jeans for work | casual summer outfit idea for the office | Cotton Cashmere Cat Hair

I no longer own the jeans I wore in the original 2016 outfit, but I do still own the Madewell stud earrings. I’ve worn those so much already that I opted to wear my relatively new Maison Miru crystal stud earrings instead for a little more sparkle and for something different. (PSA: They’re still available for the price of shipping only! I wear mine constantly and highly recommend.)

I sold the skinny jeans from the original outfit because I stopped reaching for them…mostly because I’m no longer a fan of rises that hit below my belly button. I have officially converted to the dark (high rise) side, and it is so much more comfortable! I missed having a pair of light wash skinny jeans, so I added a new pair with a 10” rise right before the pandemic hit in my pre-pandemic Madewell denim size. Of course, they’re tight on me now, lol. These definitely read more casual than the original pair because of the frayed hems (that should probably be trimmed up) but I would still wear them to the office because luckily my office is on the casual side of business casual!

I also added a bag to this look because it felt like it needed something more, and this is an outfit I’d totally wear to work! I purchased the Madewell medium Transport tote a couple of months after I started my job four years ago as a new job/birthday gift to myself and I’ve carried it to the office every day since then. The only time I don’t is when I’m traveling for work; in that case, I switch to my Longchamp Le Pliage Neo tote.

There isn’t a huge different between the 2021 version and the 2016 original except for the addition of the tote bag! So, are you a fan of my work tote…or would you wear another bag with this look?

Browse all outfits in the 5 years later series!


OUTFIT DETAILS

Amour Vert shirt / old; similar from Macy's or shop all floral styles at Amour Vert (last seen here)
Madewell jeans / old; similar (last seen here)
J.Crew flats / old; similar from DSW (last seen here)
Maison Miru earrings / exact (for a limited time, get a pair for the price of shipping!)
Madewell bag / exact (zip-top version; also available from Zappos and Shopbop)
Le Specs sunglasses / exact via Shopbop or Nordstrom
Dior Lip Glow in rosewood / exact