Hi People!!!!!
Welcome back to the newsletter! I’m sorry I haven’t been a very good pen pal lately. It has been a very busy few weeks. I’m starting to get in the groove of my new job and back to the routine of writing each day, so I hope to continue our regular correspondence soon! (I think I said the exact same thing in my last newsletter though, so no promises...) Either way, I love writing this newsletter, and I want to assure you that I am very committed to continuing it. With the new job at Betches, however, all I’ve been thinking about is dating and relationships, so I decided to use all of that as inspiration for these four outfit ideas for different kinds of dates. Enjoy:)))))))))))
For an art exhibit with a sophisticated older guy who secretly intimidates you a little bit
If your date is cultured and worldly and you’ve spent the last four years in a frat house, you might be feeling a little insecure about your own intelligence and life experience. Instead of spending the entire date trying to prove your smarts to this guy, wear a smart ass outfit like this. This way, when you stare silently at the art wondering if he’s going to buy you dinner afterward, you’ll at least appear to be having deep, complex thoughts about Van Gogh. This is a slightly more calculated usage than what I typically mean when I tell you to use clothes to express yourself, but very practical nonetheless.
For Topgolf with a guy who is going to take the competition way too seriously
Golf is extraordinarily boring to begin with and he very well might shush you during his backswing, so someone’s got to bring up the energy here. The colors and prints are justtttt over the top enough, while the shorts’ silhouette and the cardigan keep things relatively chill. (And there’s just something so golfy about cardigans, no?) He will either be amused or annoyed by your shoe choice, and that reaction tells you everything you need to know about him. He’s clearly not particularly down to earth if he’s taking practice swings at Topgolf, so why should you pretend to be either?
For a COVID-style walking date with a guy who won’t shut up about his work out routine
I hate to break it to you, but this is not going to be a walk. You are going on a hike. And normally it seems sensible to wear some sort of athleisure or workout attire for that possibility, but that would be giving up before the relationship has even begun. You have to show them that you will not submit your style to the tyranny of ambush exercise. At first he will scoff at the attire you’ve chosen for this activity, but your light, white cotton and sensible sneakers will keep you cool and comfortable all day while he gets sweaty and sunburned in whatever spandex monstrosity he’s chosen for the occasion.
For a boring dinner with a boring date
Think you can slack off just because you don’t care about this date? WRONG. I personally believe you should be dressed like Stanley Tucci might bust in and sweep you away to Italy at any moment. And absolutely nothing says, “Please God whisk me away to Capri already,” like a breezy button down, crochet shoes, and a scarf tied in your hair. Okay, even if there is no Stanley Tucci involved, people can surprise you!!! In the odd circumstance that he does, you want to be fabulously dressed but not so dressed up that he thinks he actually matters. And this is a great example of outfits that will appear very low effort and chill to a man even though it was carefully crafted by an expert (moi).
Question of the week
“How do you make the most out of your outfit?”
My answer to this question is maybe surprisingly simple, though it might differ depending on your style. Personally, I always feel like I get the most excitement, joy, inspiration, fulfillment, etc. from an outfit when I take just those two extra minutes to add something that I wouldn’t have thought about at first. Maybe it’s adding a cool sock or layering on another necklace or even taking a few seconds to intentionally pair your sunglasses with your look instead of just wearing the ones already in your car. These little details show that you put your outfit together on purpose and that you have the confidence to pull it off. So screw what Coco Chanel said about always taking an item off before you leave the house, and pause, look in the mirror, and add 1-10 more items instead.
My question for you
What do you need help getting dressed for right now? Are you going on dates? Going back to the office? Still working from home? Have a vacation coming up? Whatever it is, help me help you by leaving a comment!!!
Recs of the week
1. I really never wanted to say this, but TikTok is fun. You should try it.
2. Read Haley Nahman’s highly relatable newsletter about anticipation.
3. Check out celebrity stylist Kate Young’s new YouTube channel - There aren’t a ton of videos yet, but I think the one about mood boards has some helpful tips. Plus I really admire her personal style and work.
4. If your workplace uses Slack, take full advantage of the direct message channel with yourself. Stop fucking around with airdrop. This is a much simpler way to transfer things from your computer to your phone and vice versa.
Thank you so much for reading this week’s short and sweet and sexy lil newsletter! I hope it gives you some ideas for your next date outfit or at least a laugh at the ridiculous things we put ourselves through in the pursuit of love. I appreciate you being patient with me as I figure out my new routine, and I can’t wait to keep sharing more of my ridiculous outfit ideas and inappropriate thoughts with you!!!!!!!
Cheers,
Maddy