The Entrepreneur Who Needs Wardrobe Help For His First Hollywood Party

The Entrepreneur Who Needs Wardrobe Help For His First Hollywood Party

The Entrepreneur Who Needs Wardrobe Help For His First Hollywood Party

35, Newly Rich-ish But Socially Unprepared, West Hollywood

May 9, 2025

May 9, 2025

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DAY ONE
2:00pm: Just got invited to a major Hollywood party. At THAT producer’s house. Celebrities, and my celeb crush! I RSVP yes because... why not? Then I look in my closet and realize it screams "pre-IPO hoodie gremlin" more than "fresh-on-the-scene mogul."

4:15pm: Panic-googling "quiet luxury," "elevated basics," and "how to dress rich without looking like you're trying." I even toss around texting that hot model I blew it with…. I spiral. Finally, I just message Duckbill: "Need to look expensive but not desperate. No budget because I AM desperate. Help."


DAY TWO
10:00am: Duckbill sends me a curated list and an address where I can actually try them on (instant relief!): a navy Tom Ford blazer, Italian loafers, a tee that feels absurdly priced, until I touch the fabric. I ask for a few more investment pieces that signal taste, so I have options. They deliver, with sizing notes and alternates.

7:00pm: Same-day tailoring appointment, booked by Duckbill. I show up and feel wildly out of place. The tailor compliments the picks. I pretend this is normal. Maybe it is now?


DAY THREE
3:00pm: Duckbill checks in with grooming tips and an optional, but clearly encouraged, add-on: a stylist-on-demand if I want one. I say no, but appreciate the offer. Maybe they're trying to tell me something…?


DAY FOUR
10:00pm: Deep breath: I made it, i've schmoozed, and I'm 3 mezcal Negronis deep. This party is kinda sick! Someone asks if I’m in film. I smile and say, "Sort of." My last minute glow up worked: I blended in. No one knows this whole thing came together via my now-favorite app and warding off only 1 panic attack!

Duckbill did their job. Now I just have to keep pretending I belong here, or following the advice I preach but never practice: fake it 'til you make it.



Want to submit a Duckbill Diary? Email deardiary@getduckbill.com and tell us a little about yourself.

35, Newly Rich-ish But Socially Unprepared, West Hollywood

35, Newly Rich-ish But Socially Unprepared, West Hollywood

May 9, 2025

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