I have a quick break in between hosting game shows today, and I thought it would be a good time to check my Poshmark account and see how many dresses I bought last night. See, I go online and make a bunch of low-ball offers, and then in the morning, it’s like I won the lottery when I see which ones were accepted. Then I forget what I bought and it’s REALLY like Christmas when the boxes start showing up. And then I’m like, “What the hell was I thinking when I bought this? It’s two sizes too big (or too small) and I never wear this color. Was I drunk?” and I have to resell it and hope some other sleep-deprived, depressed woman buys it. Rinse and repeat.
Now, I know what you’re thinking: Jen, we haven’t heard from you in weeks, and it’s because you think you’re Steve Harvey and you have a shopping addiction?
Kinda.
No, I don’t think I’m Steve Harvey. Steve Harvey is a dude with a career. I’m a lady with a part-time job. However, the shopping did start a few months ago when the Lords of the game show came down and said we all had to dress better. Thanks, Steve Harvey, for setting the bar so high. The Lords wanted jackets and good shoes. It was like working at a bank again, if the bank allowed a disco ball jacket. When I started looking on Amazon for a disco ball jacket, I realized that shit is expensive and I’m a part-timer who is supposedly using this cash to pay bills. And then I remembered Poshmark! Sure enough, enough ladies had a terrific time in Vegas and now they’re looking to unload their rhinestone capes at a very reasonable price.
So, I was busy buying up jackets that used keyworks like “fun”, “funky”, “eye-catching”, and “bedazzled” when my bestie, Nicole, called me up and was like, “Are you busy next month and do you have a passport?”
I’ve always known that Nicole is freaking rockstar, but this phone call proved it because she told me she’d won a trip to an island resort and I could be her plus one.
SHUT UP.
A vacation? With my bestie (and hundreds of her co-workers)? I cleared my calendar and dug out my passport. I was ready.
I am ridiculously excited. RIDICULOUSLY. I don’t have to plan a damn thing. I don’t have to figure out how to keep my kids alive on vacation. I don’t have to walk the dogs or pick up poop. And best, I DON’T HAVE TO DECIDE WHAT’S FOR DINNER. I just show up and look pretty.
Oh wait.
THAT’S the problem.
This is a work thing. There are work things happening. There are work people there. It’s a fancy-ass resort. My friend is a BFD and these are her colleagues. I can’t be Jen Fucking Mann who walks around on vacation in her pajamas and Crocs. I can’t be Jen Fucking Mann who shows up in head-to-toe black and snarky t-shirts that say shit like, “I bite.”
I needed “resort” clothes. I have no idea what “resort” clothes are, but I’m pretty sure they aren’t a plethora of black dresses and funky jackets. So, back to Poshmark I ran.
And Amazon.
And Macy's.
And Nordstrom.
And TJ Maxx.
And anywhere else I could think of that might have something I would like and wear. I’ve purchased (and returned) a lot because I can’t quite find resort wear that’s me.
I’ve decided that resort wear is a lot of caftans. Did you know caftans are hundreds of dollars? I blame White Lotus and Trump for the price of caftans. I’m about ready to cut a hole in a brightly colored sheet and make my own.
Resort wear is also a lot of white. I hate white. I get that white is cool and clean and blah blah blah. But white needs something to “pop” against. It needs skin with some color. Unless freckles count as color, I have none.
If you aren’t wearing white, you’re wearing floral. BIG floral. BOLD floral. Floral that looks great at a resort but ridiculous at the grocery store. I can’t buy dresses with pockets that will sit in my closet for the next 10 years.
Every Google search comes back with shorts being the “perfect” outfit for a resort. Go fuck yourself, Google. I haven’t worn shorts (in public) since 1995. It ain’t happening.
Neither is any sort of dress that looks at a bra and says, “LOL, put that away. We’re free-balling tonight!” Do you know how few sundresses work with a bra? Yes, I bought boob tape, but really it’s just for the entertainment value, not the actual holding up of the melons.
And before Google even suggests I just hang out in my bathing suit, cover-up, and hat, I’ve got that look on lock. I am the Queeeeen of cover ups and big ass hats (see why I can’t/won’t wear white). I’m trying to figure out what to wear when pool cover-ups and pjs are not appropriate attire.
Linen is a big trend I’m seeing. But I’ve got two kids in college now and two dogs that enjoy the vet, I don’t have linen money. A linen caftan would bankrupt me.
Another hot look is baggy dresses. Like, super baggy. And long. The 6-foot-tall model in the picture looks cute in her giant baggy dress. I look like a trashbag with sunglasses.
I finally landed on a Reddit page where a woman gave me great advice. She said wear the black dresses I have, but pair them with an “elevated” shoe, a bright scarf tied around my hair/bag/waist, a “statement” necklace, and a dark red lip. Problem solved. I might still lose sleep over elevated shoes and bold scarves, but if I can’t find anything, I’ll bust out my disco ball jacket and really show these corporate folks how to dress for success!
Hit me with your best resort attire ideas (and red lipsticks)!
Also, I could use some good conversation starters for strangers. I typically open with, “That assassination attempt was made-for-TV bullshit,” or “I believe J.D. Vance totally killed the Pope,” or “Steven Miller is a soulless cryptkeeper-looking motherfucker who deserves nothing short of ass cancer.”
snarky t-shirts that say shit like, “I bite.”
LOL You can do better.
"I don't like making plans for the day because then the word 'premeditated' gets thrown around in the courtroom."
"The last thing I want to do is hurt you -- but it's still on the list."
Sell some of that shit that's piling up in your garage that you bought to "refinish", get online with Land's End or L.L. Bean and buy yourself a decent linen shirt that doesn't cost a million bucks, a pair of linen shorts/pants (ALSO not a million bucks) and 3 pair of colored High Tops (they now come in all kinds of bloody designs--Mary janes, platforms, etc.) and just flippin' GOOOOO!