To All the Outfits I Would Have Worn: A Digital Retrospective

If “To All the Boys I’ve Loved Before” is a story about a collection of failed loves, then this is a story about failed attempts at well, wearing clothes. Before the pandemic began last year, I couldn’t have ever imagined how much my clothes helped me feel happy, put together, and frankly, like myself. While stuck at home, my boyfriend innocently tried to suggest that I should just wear my outfits at home to feel better — even though it was just the two of us. But to be honest, that almost sounded more depressing than lounging around in my sweats — the pandemic outfit of choice. 

As the pandemic raged on throughout the course of the year, I clung to my hope that I’d be able to wear one of my beloved outfits again. I steadily invested in new pieces, even though weddings I’d already RSVP’d to were getting canceled, birthday party plans were thwarted, and when winter rolled around, all of my clothes would be hidden by a bulky puffer coat so that I could survive seeing my friends during an outdoor dining date in 30-degree weather.

I knew that I needed to ~somehow~ find a way to fill the void and re-inspire me sartorially in a way that I’ve been missing since March 2020. Well, since it’s been almost a year since the initial lockdown and social-distancing protocol is still firmly place (not to mention the fact that we East Coasters are all snowed in for the foreseeable future) I thought I’d try to play some digital dress-up at-home since IRL outings are, for the most part, still out of the question. 

For those of us who love fashion, it’s been hard not having any excuse (or, reason, for that matter) to get dressed and, you know, feel cute. Even though it may sound like more trouble than it’s worth, for me, there was nothing like a mini photoshoot and outfit styling session to lift my spirits, even if only for an hour. Here are all the outfits I would have worn, and where I would have worn them.

And to all the outfits I would have worn, I hope to rock you in public one day. Here’s to us all getting vaccinated one day very soon.

Our mission at STYLECASTER is to bring style to the people, and we only feature products we think you’ll love as much as we do. Please note that if you purchase something by clicking on a link within this story, we may receive a small commission of the sale.

Courtesy of Brittany Leitner.

1. The Mix & Mingle Suit

Here’s a photo of me pretending to mingle and absorb some serious tea-spilling at a party. I can’t tell you how much I miss strangers! I pretended I was deep in conversation for a full 60 seconds before I realized I was in my living room talking to my ring light (oops!).

This is what I would have worn to one of my friend’s wedding rehearsal dinners. It’s elegant, sharp, and not white, so I wouldn’t have to worry about clashing with the bride. This suit pictured is by C/MEO, which, sadly, went out of business during the pandemic. I’ve linked to some similar styles below.

Get the look: ASOS Design Petite Dad Suit Blazer ($74); ASOS Design Petite Dad Suit Trousers ($46); Kitsch x Justine Marjan Hair Clips ($9.97); Public Desire Afternoon Block Heels ($24).

Courtesy of Brittany Leitner.

2. The Stylish Dinner Guest

Hello, my beloved (and heavily discounted) Chloe boots. Boots like this deserve a dress that does them justice, which is why this puffed sleeve babydoll dress by Ganni is the perfect pairing. I would have worn this to a business dinner with one of my boyfriend’s associates or with a brand rep for an upcoming story of my own. In this fantasy (and in this feminine but bold look), I would have been the natural-born conversationalist that I am, and at the end of the meal, would have suggested the perfect spot for us all to get a cocktail afterward. 

Get the look: Ganni Checked Organza Minidress ($206); Glamorous Black Cut-Out Ankle Boots ($44.80).

Courtesy of Brittany Leitner.

3. The “Just Coming Over to Hang” Cool Girl

This would be a great look to fool my friends into thinking I was a relaxed, “cool girl,” — if only I could go into their houses without being worried that we’re passing a grave virus back and forth. I also could see myself wearing this if someone casually invited me to an outdoor brunch during the spring.

Since I have literally never enjoyed eating outdoors until the pandemic (the noise, the cars, the chance of a rat running over your foot), I would have begrudgingly said yes and nuzzled safely into my oversized button down for comfort.  Luckily, this is one outfit that I can enjoy wearing around the house, even though, sadly, no one will see me in it. 

Get the look: Aerie Real Me High-Waisted Cross Over Leggings ($44.95); Collusion Mixed Check Mini Shirt Dress ($40); Electric Picks Mini ID Necklace ($98); Truffle Collection Chunky Ankle Boots ($48).

Courtesy of Brittany Leitner.

4. The Themed Party Attendee

In my mind, a themed party translates to “wear whatever you want, just make it funky.” Look at this outfit and try your best to picture it with me. ’90s theme? Throw up a Spice Girls peace sign in all your pics. Western-themed? Add a cowboy hat. Luau themed? Add a lei just bright enough to match the top. 

I would have worn this outfit with this Zara choker for under $7 and called it a day. My Instagram would have been popping with this liquid neon look — the color would’ve surely been enhanced by VSCO or Afterlight — but alas, I’ll just have to tally up the imaginary likes and comments in my dreams.

Get the look: Mia Vesper Neon Pink Tiny Top ($150); Levi’s Black High-Rise Skinny Jeans ($16.13+).