I have selective memory when it comes to outfits. I seem to easily remember the ones that stuck in my head like a burr the day I wore them for all the wrong reasons — my pants felt tight, my shoes were all wrong, my shirt had an enormous wrinkle I was too lazy to deal with that morning. As for the many outfits that have made me feel like my best self, the products of kismet that somehow came together perfectly, that moment of sartorial clarity? They’re akin to the stuff of dreams; immediately hazy, as if they never even happened.
While this forgetfulness can be great for egging on my creative juices by necessity, it’s also incredibly inconvenient whenever I’m feeling lazy. Sometimes you just need a go-to fantastic ensemble that’s worked in the past and will undoubtedly work again, you know? To that end, I reached back into the recesses of my mind, otherwise known as the evidence documented on my Instagram feed, to refresh my memory vis-à-vis an outfit that made me think, “Damn, I did that!” I also asked my coworkers to do the same, because there’s no such thing as too much self-inspiration.
Harling, Fashion Editor (Me)
Where did you wear it? To the office on July 31st, 2018 — to be exact!
Why does this outfit continue to stick out in your mind? As forgetful as I am about my best outfits, I can say with confidence that most of them were born in the height of summer. This is the season when I am most delighted to be and therefore most delighted to get dressed. Part of that has to do with how warm and sunny it is outside, and the overall mood of jubilance in the air, but sartorially speaking, I find it easier to pick out outfits in the summer because I can’t overthink things too much by virtue of the weather. It helps me simplify, and not in a way that strips my outfits down to boring basics but rather in a way that makes each component of them speak with uncrowded specificity. Such was the case with this all-white ensemble, which manifested during a phase in which I was substituting gym shorts in favor of regular shorts with vigor. The result was a look that had a point of view, but not at the expense of ease or comfort. I can’t wait to wear it again.
Leandra Medine, Founder
What are you wearing? A cotton poplin bathrobe from Sleepy Jones with baggy floral brocade straight leg “jeans,” and a black tuxedo blazer festooned by various sizes and shapes of multi-color rhinestones.
Where did you wear it? To a dinner party in Noho sometime in 2015.
Why does this outfit continue to stick out in your mind? In my view, there is a sweet spot of about seven years that lets you objectively appraise your style and this one falls into that time period, clocking in at a spritely four years young. Let me explain this logic: When an outfit is older than three years, enough time has passed for it to look dated, so if you still like the outfit, that can mean it’s actually your style. But if it’s older than 10 years, enough time has passed that it could be cycling through the collective fashion trend consciousness, potentially rendering it “back in fashion.” When I am reminded of the time I wore a striped robe as a top under an ambitious tuxedo blazer with “jeans” that are floral brocade (and not technically reversible, but very much wearable on either side), I feel strongly that I’d 10/10 wear it again right now. So there u have it.
Starling Irving, Office Manager
What are you wearing? A thrifted vintage raincoat, pants and belt from Horizons Vintage, a thrifted vintage blazer from Mirth Vintage, a thrifted vintage sweater from Awoke Vintage, a thrifted vintage necklace and broach from Flavour Upstairs, and earrings from Etsy.
Where did you wear it? I wore it while visiting my parents in their new hometown, Victoria, British Columbia. It’s like a very rainy version of Neverland there.
Why does this outfit continue to stick out in your mind? Like most of my wardrobe, this outfit is completely made up of secondhand items (except for the earrings which were $25 on Etsy). I bought the raincoat at Horizons Vintage for $110, which is on the steep end of what I pay for clothing, but I’ve gotten a ton of wear out of it. It keeps me dry and makes me feel like the Queen Mother in the Scotland beach scene on The Crown. I was layered up with cashmere at the core and the look felt like the coziest, most practical version of my best self.
Elizabeth Tamkin, Market & Affiliate Strategist
What are you wearing? Vintage silver metallic quilted shorts I scored on Etsy for $25 with a ribbed tank from Amazon for $7.25 for a pack of two, G.H. Bass Weejuns loafers, Holiday The Label Leisure Seekers sunglasses with 2 Lucy Folk eyeglass chains, a Babaà Knitwear sweater and Imago-A bag
Where did you wear it? To lunch with my boyfriend followed by a hunt for the perfect new houseplant which we wound up finding via a “Felt Plant” from Crest Hardware in Williamsburg. He carried it home. I didn’t help 🙂
Why does this outfit continue to stick out in your mind? Because I felt really good about myself and generally happy on the first 70-degree day of the season. I love walking and these shoes are comfortable to stroll in. I also LOVE a good vintage score so I felt like I was winning every wiggle in my walk with these shorts.
Jasmin Aujla, Director of Partnerships
Where did you wear it? To the opening of the Gucci store on Wooster Street last April.
Why does this outfit continue to stick out in your mind? Typically if I’m going to a formal event/party, I’ll be in some sort of dress, but in this case I went in a totally different direction and opted for what was essentially elevated bedroom attire. I remember feeling so comfortable and slinky. Who doesn’t want to feel slinky?!
Matt Little, Head of Business Development
What are you wearing? Craft paper top, H&M shorts, rope and the box that a mini disco ball arrived in.
Where did you wear it? A “paper doll”-themed birthday party last summer.
Why does this outfit continue to stick out in your mind? Primarily because the cut-out eyebrows and highlighter made me feel like a supermodel — but also because the experience of making the outfit was so fun , and it made me feel like a cooler, more confident version of myself. It was also a more show-y presentation than what I typically opt for, which was both empowering and kind of scary (but mostly great).
Haley Nahman, Deputy Editor
Where did you wear it? To work a few weeks ago (my outfit memory is very short, and my sense of style changes often enough that I typically feel disconnecting with how I dressed even six months ago. Not sure what that says about me.)
Why does this outfit continue to stick out in your mind? I forgot about it until I scrolled my Instagram, but I remember feeling particularly great in it because it wasn’t something I would typically put together and yet it felt distinct to my point of view (I wasn’t emulating a look, merely following an instinct). My foot has been injured for the past six weeks and I’ve been forced to wear sneakers, which has been fun in that it’s encouraged me to put things together that I might never have otherwise. When I do that and hit on something that feels reflective of my taste, it’s affirming.
Emily Zirimis, Visual Manager
What are you wearing? Rachel Antonoff jacket, Old Navy jeans and shirt, Trademark bag, Superga shoes and Laura Lombardi earrings.
Where did you wear it? To work
Why does this outfit continue to stick out in your mind?As much as I may try to sway away from it, the reality is that you can really never go wrong with a pair of jeans and a striped t shirt. I also really love this Rachel Antonoff trench, and it makes me excited to think that hopefully more luxury brands will continue to expand their sizing in the near future, which will allow me to participate in wearing fun pieces like this! Overall I like the balance of simple classics with a statement coat, which is why I think this outfit works!