Instead of sharing a sneak peek of this week’s Dear Baby, I thought I’d do a quick call for style prompts: You send me scenarios for which you want outfit ideas (if you want/give a shit), then I’ll pick some, get dressed, and over-pathologize my choices in a future newsletter.
You’re going to see lots of high achieving folk who have “smashed it” during lockdown and you’re tired and feel happy for them but also sad - and you want to look great to even things out.
A full year in soft, comfy clothes means you can't stomach wearing hard clothes again, but you're a thot who gets energy from looking like a dime piece-- what are some easy, breezy, sexy outfits to wear?
You’re going to a friends 30th in the park. You want to look completely fab while you reconnect with long lost pre-Covid friends and acquaintances. How do you achieve the perfect balance of chic and practical, while accommodating the fact that you will a) ride your bike to the park and b) most likely be sitting on a blanket/ the grass. TIA!
I have a friend’s wedding in June and I wanna look really cool and stylish but also not trying hard obvi. I’m from Chicago and the wedding is in Louisville, I don’t think it’s black tie but I don’t want to look basic..... I hate weddings
2) first day back at the office but you’ve optimistically sold everything thing you used to wear to work on poshmark and only have athleisure and your weekend clothes, maybe a button down
You‘re working from home, but have little errands to run throughout the day and it‘s that in-between weather where no jacket seems a bit risky but any jacket is too warm.
You’re going on your first date with a girl after only dating men and you’re so excited to explore your sexuality but you only really know how to dress for the male gaze in a dating/sexy situation and you’re NERVOUS
You just moved to a new state with your boyfriend and he suddenly breaks up with you. Now you’re a single gal living on your own in a new state, going on your first date in 4 years WITH A GIRL!!!
Reintroducing yourself to friends you haven’t seen or maybe talked to much through the pandemic. AKA, a chance to try something you’ve wanted to try but haven’t felt comfortable trying due to it being pretty divergent from your “normal” style.
It's early fall in Hudson Valley, and your planned elopement has turned into a 15-person family-only wedding (Mom's guilt trips still work on you). Weddings in general give you hives, and so do lace, sparkles, weirdly tiny buttons, and strapless necklines. It's in your backyard, and you're most excited about SHOES.
Outfit for living in your yellow 70s motorhome while traveling in the south and you want to look cool but also not so cool you alienate/horrify the rural southerners you find yourself around and also you’re near the woods so there are ticks you need to keep off your body
omg i live in the south and am so happy someone in a yellow motor home will be zipping thru! most of us aren’t easily horrified :) i would suggest lots & lots of layers bc it is hot and muggy a lot of places here & already hitting 80 in april. hope you have the best time!
You’re going to see lots of high achieving folk who have “smashed it” during lockdown and you’re tired and feel happy for them but also sad - and you want to look great to even things out.
A full year in soft, comfy clothes means you can't stomach wearing hard clothes again, but you're a thot who gets energy from looking like a dime piece-- what are some easy, breezy, sexy outfits to wear?
You’re going to a friends 30th in the park. You want to look completely fab while you reconnect with long lost pre-Covid friends and acquaintances. How do you achieve the perfect balance of chic and practical, while accommodating the fact that you will a) ride your bike to the park and b) most likely be sitting on a blanket/ the grass. TIA!
I have a friend’s wedding in June and I wanna look really cool and stylish but also not trying hard obvi. I’m from Chicago and the wedding is in Louisville, I don’t think it’s black tie but I don’t want to look basic..... I hate weddings
+1 for summer '21 wedding looks
Another +1 on summer wedding
Another for wedding ideas please!
youre having friends over casually and want to be comfy but still feel cute so you don't go to bed at 10 pm
1) Zoom job interview
2) first day back at the office but you’ve optimistically sold everything thing you used to wear to work on poshmark and only have athleisure and your weekend clothes, maybe a button down
^ #2! this is me
BRILLIANT IDEA, MS. NAHMAN!!
Omg E Jean Carroll!? Thank you!!
You‘re working from home, but have little errands to run throughout the day and it‘s that in-between weather where no jacket seems a bit risky but any jacket is too warm.
ooo i second the jacket or no jacket question
You’re going on your first date with a girl after only dating men and you’re so excited to explore your sexuality but you only really know how to dress for the male gaze in a dating/sexy situation and you’re NERVOUS
this makes me really excited for you!
this just confirms my suspicion that more women/non-men are queer after quar!
You just moved to a new state with your boyfriend and he suddenly breaks up with you. Now you’re a single gal living on your own in a new state, going on your first date in 4 years WITH A GIRL!!!
omg if this is autobiographical CONGRATS AND GO GET IT ENJOY YOURSELF <3
when you want to expand the “elastic waist” category of your wardrobe without looking like a retiree playing bocce on a cruise ship
Reintroducing yourself to friends you haven’t seen or maybe talked to much through the pandemic. AKA, a chance to try something you’ve wanted to try but haven’t felt comfortable trying due to it being pretty divergent from your “normal” style.
It's early fall in Hudson Valley, and your planned elopement has turned into a 15-person family-only wedding (Mom's guilt trips still work on you). Weddings in general give you hives, and so do lace, sparkles, weirdly tiny buttons, and strapless necklines. It's in your backyard, and you're most excited about SHOES.
congratulations!!!! would love to see what you decide to wear!
Outfit for living in your yellow 70s motorhome while traveling in the south and you want to look cool but also not so cool you alienate/horrify the rural southerners you find yourself around and also you’re near the woods so there are ticks you need to keep off your body
omg i live in the south and am so happy someone in a yellow motor home will be zipping thru! most of us aren’t easily horrified :) i would suggest lots & lots of layers bc it is hot and muggy a lot of places here & already hitting 80 in april. hope you have the best time!
I think post-pandemic outfits should be a no holds barred affair so I propose:
- a cryptozoologist on a book tour in the Pacific Northwest,
- "The Big Lebowski" but they are all insta influencers,
- what River Phoenix would wear in 2021,
- a watermelon :)
hahaha love this energy
Upvote for "The Big Lebowski" but they are all insta influencers, which seems like it'd fit a Haley style post?
you’re trying to finish your phd dissertation and want to feel like a critical and lively academic instead of an anxious, inarticulate blob