Here it is! as requested by a majority of my beloved instagram followers in a story poll. If you want to join them in expressing your right to vote (on what lands in your inbox next) follow Kind of Cool here. This is a long ‘stack so desktop or in-app will be your best bet for happier reading.
I feel it’s necessary to let you know straight off the bat that I’m writing this as somewhat of a mantra in the hopes that I get to dress up for at least one date this year. I’m not even particularly bothered if it’s a great date or not, though obviously I’d prefer that it was. I just want to get all intentionally dressed up for the occasion. Love a good getting ready montage. And so these are a few fitting formulae for a few date formats you may be lucky (or unlucky?1) enough to partake in.
If you’re not familiar with The Dress Code and it’s formula2, allow me to kindly direct you to THE DRESS CODE 001 for the 411.3
Dressing for dates should, in my mind, combine three key things: feeling comfortable, feeling cool and feeling hot4. Though these appear simple upon reading, amalgamating all three in just one outfit can be a challenge. But I’m going to try.
I’ve tried to make sure there’s something for everyone in this Substack since some of my new subscribers are here from the menswear-focused writings. Either use the contents list to the left if you want to jump to a specific section. Or dramatically scroll to “A THIRD DATE.” for something with a specific menswear-focus. Really though, all of these can be applied to everyone if you’re imaginative enough.
IT’S A DAYTIME DATE AFTER TEXTING NON-STOP FOR TWO WEEKS. HOPEFULLY YOU HAVEN’T RUN OUT OF THINGS TO SAY.
Picture this
The only definite details are as follows: there will be a couple of iced americanos, a walk around a park that maybe has a duck pond and you’re supposed to be meeting in 45 minutes. It’ll depend on the weather so you note to self that trousers will be the safest bet for taking on any unexpected last minute changes.
Your first coffee of the day has worn off and this iced americano couldn’t come any sooner. You’re kind of hoping it’ll encourage a good amount of hyper chatting since you’ve been texting so much that now there may be a lull in real-life conversation. It’ll be fine. You shake it off and put your morning playlist on repeat as tops, t-shirts and jumpers fly across the room from your rummaging. You want it to seem like the outfit didn’t result in turning your wardrobe inside out. And there’ll be walking so shoes have to be semi-sensible. And no bag is not an option. Minnie Riperton’s ‘Les Fleurs’ plays from your laptop as the open window lets in a slight breeze coming in from the coast. It’s maybe the best day so far this week for a walk with someone new and an afternoon of questions and answers. You check the time and grab your keys from the small ceramic dish by the door.
Inspiration pull
Trousers are safe and comfy. Doesn’t mean they must also be boring. Opting for light wash denim will state the main colour of your fit. Going for a loose dark denim or trouser will ground a solid base for your top half. Any adventurous patterns will claim focus. Decide which of those three options you truly feel great in on the given day and you’ll have a starting point. The next step is likely texture. A light, semi-sheer billowy shirt or a fine and fitted white tee are easy. Maybe a super sheer knit but paired with a statement balconette bra like Salma Hayek’s in this substack, for sexiness with subtlety in darker tones. Exaggerated elements add textures too, like an ultra batwing top in a thick material for drama without formal feel or a plethora of pleats to catch the light on a seemingly simple black top.
Next would be layering. A boxy leather jacket, worn at first and later dropped over the arm as the day gets warmer. A chunky v-neck knit to counteract your shirt length and slightly cinch. A drop-shoulder loose blazer with a boxier fit as an extra layer that adds smartness to your casual cool. Then shoes need to be walkable but that’s subjective. A mini heel can elevate a basic fit by heightening its femininity and sometimes they’re not the worst for strolling in. A classic worn-in white trainer brings a vintage, sports-wear nod to a simple look for something playful. Or a statement shoe can keep you walking even when day turns to night and you find yourself still chatting at the bar on the corner. Just as long as you love wearing it all, that’s what counts. Pick your old faithful shoulder bag and you’re good to go.
Irl Keyword Searches
batwing structure wool top
plissé pleated top
very sheer light high neck top
classic stretchy white t shirt, short sleeves
baggy jeans, add. dark grey wash / pale blue wash / brown corduroy
faded floral pattern high waisted jeans
sheer white and black striped shirt, add. asymmetric hem
heavy leather biker jacket, add. minimal design / simple
v neck chunky knit mohair jumper
vintage short boxy blazer jacket
reebok classic club c vintage
strappy kitten heel
YOUR DATE GOT A COVETED RESERVATION AT THE NEWEST RESTAURANT AND THE UBER IS BOOKED FOR 8PM BY WHICH TIME YOU’RE HOPING THE RAIN WILL HAVE LET UP A LITTLE.
Picture this
Last week you read a review about some new restaurant in the paper you found on the train seat next to you. Apparently they’re hustling for a Michelin star thanks to the chef who previously worked at somewhere or other that your parents really liked. That same night your date mentioned a booked reservation and a pickup time. Now here you are staring at the pile of clothes on your bed that consist of your “fanciest pieces” wondering if it’s too late to cancel as the rain lashes down onto the pavement outside. You wouldn’t be canceling because of your date obviously, but because of your clothing-induced frustration that appears like clockwork every date night.
More than anything you want to strike balance in whatever you end up wearing. There needs to be a classy feel to it for contextual reasons. Both date night no. 2 and date night no. 200 deserve the same fashionable effort. But you still want to feel like yourself and not swallowed up by a mass of clothes just to sit down and eat plates holding portions the size of your palm. The hammering rain threatens to ruin every pair of shoes you own and have you show up à la drenched rat. A chic one at least. You hold up options in front of the mirror and discard them behind you just as quick. You look out your strongest umbrella.
Inspiration pull
As you can see in the inspiration pull here there are a lot of different aspects in these outfits. But what I think pulls them into the same part of my brain is that they follow lines. And that is my main focus for this outfit. Follow your lines. I love longline pieces like midi-maxi skirts, dramatic long sleeves on otherwise simple tops, co ords that could pass for long dresses and jackets that feel a little wrong wrapped around all of this, used simply as a means to get from one door to another.
Look at clothing that drops hints. It doesn’t tell you honestly. The answers are found in movement and moulding as you wear and live in it. This is definitely a scenario that calls for a bit more of the sexy side but it doesn’t have to be in obvious ways. It could be the act of unveiling a perfectly fitted outfit from under an oversized men’s leather jacket. Or it could be peep-toes peeking from below the hem of a long skirt when you take a step. Or do as Diane von Furstenberg does and have the light surround you as it bounces off a statement necklace, in your simplest slip dress. Go for similar tones, if not matching and soft looking materials and ask yourself if you’ve ever felt better before you leave. Here’s hoping the answer is no.
Irl Keyword Searches
plissé long skirt
plissé high neck sleeveless top
leather maxi skirt
oversized men’s leather jacket
butter yellow short sleeve flowy t shirt style top, add. flattering waist
butter yellow soft maxi skirt
burnt orange stretch maxi skirt
burnt orange long sleeve top, add. asymmetrical sleeves / hem
beige suede corset style minimal top
beige suede straight leg / wide leg trousers
vintage clutch
vintage peep toe heel
leather strappy sandal heels
gold disc statement necklace
chunky silver short necklace
A THIRD DATE. IT’S SEEMING LIKE A SURE THING.
Picture this
Your date always looks good. Or has done on the two dates prior. And maybe you’d never admit it but you kind of hope that people look at you two together and say “that’s a good looking couple”. So you aim to match the style energy. It deserves effortlessness from afar with attention to detail up close. You know you want that sartorial compliment in their group chat the next day.
You both mutually agreed on one of those wine & ice cream bars that you both pretend to hate together but secretly love. You both got ads for it on Instagram and one of you has a very loose connection to the owner. Friend’s brother’s ex’s dog’s cousin’s owner’s girlfriend or something like that. Luckily, this gets you ahead of the internet-hype queue and at a table on the terrace which is just metal garden furniture painted in a colour straight out of a 1970s home improvement book. The interiors are swimming in mid-century modern decor that remind you of your [grand]parents’5 home. For some reason, there is a DJ set taking place in the close quarters of this bar. But at least you're outside in the sun listening to your date ask you third-date-questions while you wonder if they’ll go home with you later.
Inspiration pull
Here’s the train of thought. I’m thinking a laidback spring lightness with a late evening layer that possesses texture6. With denim at the core. An example would be 2 short sleeve t shirts layered. I suggest different colours and different necklines to create levels. Then a trusty denim. Something strong, cotton and worn in areas so that light patches have taken over. A belt for a slight metal focal point and a lightweight wool sweater in a complimentary (neutral) colour. Wouldn’t hurt to have a denim jacket held in hand until needed for the evening chill. I think the jacket hold is an underrated key to harnessing that effortlessness as it adds a little undone slouch.
Another play on the style keywords above might be with a cotton shirt. Often the ones that have “heavyweight” written on the label have a really nice fit as they hang well. Buttons done to wherever you prefer. Think cool/casual more than conservative or considered. A dark linen button-up could also be great here with the trusty denim & belt. Whether you tuck it in or not or just a little on one side is up to you but do it haphazardly while walking to the kitchen or something and it’ll probably look better that way. Opt for the go-to shoes you tend to wear with jeans. Maybe a sturdy boot or a dark trainer. It matters more that you like walking in them and you’re not barefoot.
Irl Keyword Searches
heavyweight cotton shirt, alt. button-up
100% cotton light denim jeans, add. fit style e.g. straight leg, baggy, carpenter
boxy men’s tee, short-sleeved, add. colour preference as you see fit
fine knit jumper, add. round neck (or neckline preference)
chunky knit wool jumper
dark linen shirt
men’s slouchy t shirt
100% cotton denim jacket, add. vintage / wash preference
simple metal buckle leather belt, alt. minimal
basic sweatshirt, add. colour / slight oversized
vintage sports team cap
[brand suggestions]
levi’s
evisu
lee
wrangler
nudie jeans - look for the “tuff tony” fit
carhartt
paraboot
weekday - do a good men’s tee shape
arket
ralph lauren (vintage)
calvin klein
bally - colour palettes in their recent runway styling have been solid references and vintage leather pieces are incredible finds
If you made it this far, thank you for reading. I’m considering setting up a paid subscription option as these style-based series’ develop. It would be a very very small monthly amount but let me know if you’d be interested/up for it. OR if you’d hate it and it would make you cry leave a comment below.
Also wanted to note that I am working on bettering my references for more inclusivity and diversity, so please forgive me if you feel a lack of relatable representation here. It’s really important to me to give everyone options and inspiration that suits them despite how shit Pinterest is at helping me find it. I will do better!
See you soon.
depending on how good your dates tend to go but in this dating climate I’ll keep my fingers and toes crossed for you
where have you been ? are you even subscribed ?
a numerical code saying that I declare we as a society must resurrect. it was so c*nty. and while we’re at it bring the sexy flip phones back !!!!!!!!
not according to a thermometer
I don't know how old you are x
i’ll continue to say it