OMG I can’t believe you’re here!
Hi People!!!!! Welcome to the very first edition of my newsletter, thanks for being here! Keep reading for all my musings on getting dressed for a first date, some examples of outfits I wore, and fun ideas for you to recreate.
The Surprising Emotions of Getting Dressed for a First Date
If you’re not one of the many people that I‘ve described my recent escapades to in great detail, here’s some news: I recently went on my very first first date. And a whole bunch of first dates after that. A symptom of quarantine boredom (and quarantine heartbreak, but that’s a story for another time), I downloaded Hinge one night after a few margaritas with my sister. After a few days of swiping, I had agreed to approximately 87 different dates upon my return to Dallas and the end of stay home orders. It wasn’t until 6:42 PM on the night of my first date at 7:00 that I realized I had no fucking clue what to wear.
We’ve all experienced that dramatic “UGH I have NOTHING to wear!!!!” feeling standing in front of an overflowing closet (closet clean out guide coming soon), but this time was different. A first date with a rando you met on Hinge is a weird-ass experience to begin with. You have basically no introduction to each other except a few text messages and the carefully selected photos on their profile, which may or may not be what they actually look like. Walking into the first meeting feels like arriving at a job interview that you only prepared for by shaving your legs and double checking your deodorant. I assumed my response in this unfamiliar territory would be to find comfort in style, to put on an outfit that made me feel most like myself, and my mindset would be transformed. But when I reached for my clashing prints and my oversized sleeves, it just didn’t feel right. I felt the unfamiliar urge to just wear something “normal.”
While I didn’t have time to dive into that feeling 15 minutes before I was supposed to be ready, I noticed it coming up again and again with each first date. I ended up throwing on jean shorts, a white tank top, black sandals, and my usual colorful jewelry and called it a day. I was pleased with the outfit in that I looked good—the white tank top is a laid-back knit that’s sexy in a very casual, not-trying-to-be-sexy way, the jean shorts were flattering and comfortable, and my jewelry gave me a little sense of myself. But these are not my usual qualifiers for a good outfit. I’m usually going for interesting over attractive.
As someone who wholeheartedly believes in self-expression through style, this threw me for a bit of a loop—maybe not a full-blown identity crisis, but a tiny, mini, baby identity crisis if you will. In case you couldn’t tell by the number of mirror pics I post on Instagram or the newsletter you’re reading at this very moment, I’m not exactly shy about my personal style. There aren’t many occasions where I censor my style because in most situations I’m more comfortable looking a little offbeat than not. Maybe it’s the people-pleaser in me that needs a bold introduction to keep myself from being annoyingly palatable. I pride myself on having a big personality and big opinions and sticking to my guns, but I only recently realized how much my sense of style empowered me to be that way. When I walk into a room full of new people dressed differently than everyone there, it gives me permission to be different too.
What I didn’t yet recognize is that there are varying levels of intimacy involved in how we dress (or at least how I dress). For my friends who know me and my style well, there’s zero hesitation when I’m deciding what to wear. I put on what feels right that day and roll with it because my purse choice isn’t telling them anything about me that they don’t already know. On the opposite end of the spectrum, when going out to a crowded bar with lots of new people to meet or getting dressed for a new-ish job, there’s more presentation involved. Maybe for some people this puts on the pressure to blend in, to misrepresent themselves and their style, but like I said before, it’s my style that gives me permission to be myself in these less intimate situations. My outfit (at least in my mind and that’s what really counts I suppose) gives an introduction to who I am, and then I feel emboldened to stay true to that. So you can imagine my surprise when that instinct, the desire to express myself through style, an exercise I religiously practice, abandoned me when I wanted to feel like my best, most confident self.
My knee jerk reaction was to be mad at myself for feeling this way. This isn’t meeeeeee. I take great pride in my style and the sudden fear of showing it off was something I haven’t experienced in a long time. When thinking about style in terms of intimacy however, it doesn’t feel all that shocking that I didn’t want to put on the most “Maddy Paul” outfit ever. If my style says as much about me as I believe it does, then of course fully revealing myself that way on a first date would be uncomfortable. It feels like an overshare, exposing in the same way that diving right into my relationship history or listing all of my deepest, darkest fears on the first date would be. Discomfort not from a fear that they wouldn’t like my outfit (I got over that long ago) but from a fear of letting someone in too much too soon.
Through this lens, my feelings of vulnerability started to feel like a victory for my personal style. When you show who you are by how you dress, it makes sense for that display to be a little segmented based on the social environment. The same way I wouldn’t want my boss to know everything I tell my friends, I don’t want a blind date to know everything I feel my truest style indicates about me as a person.
The moral of this long story is it’s okay to hold back every now and again, to be aware of social boundaries and how they make you feel. If you’re dressing to express yourself, those feelings are equally valid in the equation, so don’t let a loudmouth like me constantly preaching the gospel of individuality tell you any different.
Anyhoo, now that I‘ve used you as my therapist for 1000 words, here are some practical tips for getting dressed on a first date.
1. Do your research. Google the place where you’re meeting up to get a feel for the vibes, and look back at your date’s photos to see how dressed up he or she is likely to be. I don’t think there’s anything wrong with being over or underdressed compared to your date or the location (follow your heart, chase your dreams, etc), but it definitely plays into the vulnerability I already described ad nauseum.
2. Comfort is key. This is one of my commandments for getting dressed in general, but it’s especially relevant in dating. No, I’m not suggesting you wear your comfiest sweats to a dinner date, I haven’t completely lost my mind. Comfort in this case is more about confidence. Can you move easily? Are your pants staying up? Can you sit down without your vag making an appearance? If you’re pulling uncomfortably at your clothes the whole time you’ll be distracted from the conversation and you won’t seem as confident.
3. Drop some hints. None of this deep dive into the intimacy of getting dressed is to say that you should put on the most boring, neutral, crowd-pleasing outfit you own. You want to leave little breadcrumbs of personality that gradually lead to the whole enchilada of your style/self. For example, on the first date maybe it’s just your favorite unique jewelry. Then on the second date, it’s a more statement-making top. For the third date you could throw some clashing prints in there if that’s your thing. Do you see what I’m getting at here? You gradually let this person in with your style the same way you would with conversation. It’s quite possible that the other person in this equation will not even notice or care about these subtleties, but I like to think it adds a little mystery and intrigue.
Example of a date outfit evolution
Here’s what I wore on my first three dates with a guy I have referred to as “The Snob” among my friends. Though he was much less snobby after date #1 to be fair.
Date 1: Drinks at a very trendy bar
In retrospect, I probably could have put on heels for this one to match the vibe of the restaurant, but whatever. This dress is comfortable and cute and just bold enough for me to not feel completely basic wearing it with low key accessories.
Date 2: Wine and charcuterie at a cozy restaurant
Breadcrumbs people! For the second date I went with a bolder necklace, bright red bag (not well captured here, oops), and these funky jeans with colorful stripes running down the back. Still not the wildest outfit, but it’s a little more “me” than the first.
Date 3: Not one but two sushi dinners in the same evening
And finally, my personal favorite styling trick comes into play: clashing prints. Again, this man probably did not notice this style evolution in the slightest, but it made me feel confident and safe. I’m still undecided on whether or not this guy gets a fourth date, but I’ll keep you posted.
First Date Outfit Ideas
For a casual yet boujie dinner date (think tapas!) when you want to keep a little mystery alive:
Start with your favorite flirty skirt because this is a date after all.
Button-downs are great for date #1 because you can customize your sexy level! Date’s breath smells like dog food? Button that bad boy alllllllllll the way up. I gave you two options here because, as you can see, this outfit looks equally fantastic with a solid or printed option. You do you.
Add another little pop of color with your sandals. Like I said in my emo rant above, the goal is not to be boring. I’m personally a flats-on-the-first-date kind of girl, but you can easily swap these out for a kitten heel or wedge if that’s your thing (or if your date is, like, super rich).
For your ears, I like these teardrop earrings because they’re fancy and fun but not overly distracting.
I know, I can’t believe I’m recommending a neutral crossbody bag either, but I did in fact wear a simple brown bag on multiple first dates. I think it keeps this look grounded, no?
Finally, layer on as much dainty gold jewelry as you can without suffocating yourself. Or cheat with a layered necklace like this one.
For a coffee date when you want to get all the crazy out up front (or you just don’t have the same weird outfit intimacy issues as me?)
Start with a striped tee because stripes go with everything and don’t let anyone tell you different.
Neon! Flowers! Draw as much attention to that derrière as humanly possible! Maybe get a flashing sign if you can find one??
Add some twisty gold hoops to express your love for croissants. If you don’t love croissants you should probably just unsubscribe now.
Pearls because you’re a lady and smiley faces because you are a ray of fuckin’ sunshine!!!!!
Layer on a four leaf clover for good luck, obviously. Other good luck talismans you could string on a necklace include: your lucky number, a horseshoe, a pair of fuzzy dice, a rabbit’s foot, the options are endless.
Maybe throw some neutrals on your wrist area to show you are capable of wearing beige when absolutely necessary?
Fun fact, you can fit a full-size bottle of wine into this surprisingly versatile tiger bag from Man Repeller’s accessories collection. These are no longer available, but you can borrow mine if you ask nicely. Generally think adding a third print is always a good idea though.
Flats! Because nothing else about this outfit was trying too hard. Very nonchalant, I swear!
I like you a lot
Oh hey, you stuck around this long? You must really like me! The feeling is mutual. If you have any questions, comments, concerns etc. feel free to leave a comment on this post or reply to this email if you want some one on one time. I will be giving expert (lol) style and life advice in newsletters to come, so submit all your burning questions. If you don’t, I will be forced to make up really embarrassing ones and put your name on them. :)
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