Thursday–Sunday · Manhattan · Personal Days
Thursday
Travel day → Night out
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✈ Travel
Half-zip doubles as a blanket on the plane. Land looking put together.
Ivory tank
Black half-zip
Black joggers
Gold Adidas
Tan scarf🌙 Night Out
Clean, sharp, and the vest gives the red dress an edge. Statement earrings here.
Red dress
Black vest
Black flats
Leopard bagFriday
Library · Bryant Park · NY Liberty
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📚 Library + Bryant Park
Hot pink cropped top + ripped jeans + denim jacket is still a strong look. Half-tuck the pink top to keep the proportions right.
Black tank
Hot pink top
Ripped jeans
Denim jacket
Pink Adidas
Dino pack🏀 NY Liberty Game
Black tee + olive jacket + ripped jeans + gold Adidas is a clean, effortless game-day look. Frees up the denim jacket for later in the trip too.
Black tee
Olive jacketRipped jeansGold AdidasDino packSaturday
Biking · Picnic · Shakespeare in the Park
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🚲 Biking (morning)
53° in the morning — half-zip is necessary. Comfortable for the ride.
Atari teeBlack half-zipBlack joggersGold Adidas🧺 Picnic → 🎭 Shakespeare
Atari tee tucked into the pleated skirt is an unexpected combination that totally works. Bike shorts underneath for comfort. Bring the camel blanket in your bag — you will need it at Shakespeare when temps drop to 53°.
Atari tee
Pleated skirt
Bike shortsOlive jacketPink Adidas
Striped scarfSunday
Grey Dog Brunch · Museum · Night out
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☕ Brunch + Museum
Floral dress + denim is effortless and camera-ready for a Sunday brunch. Tan bag keeps it clean — the leopard's orange accents clash with the floral palette.
Floral dressDenim jacketBlack flats
Tan bag🌙 Night Out
Black vest over black tank + wide-leg trousers keeps the night-out look sharp and intentional. Already packed, already earning its place.
Black tank
Black trousersBlack vestGold AdidasLeopard bagMonday–Sunday · Brooklyn · No BS Retreat
Monday Retreat
Travel to Brooklyn · Evening planning ☔ 40% rain
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🚇 Travel
Olive jacket is your best rain-day option. Real 40% chance — don't skip the umbrella.
Gray teeOlive jacketBlack joggersGold AdidasTan scarf🌙 Evening Planning (optional swap)
If you want to feel cuter/cozier for the evening, add the pullover. Easy swap, same bottoms.
Brown pulloverTuesday Retreat
Year 2 with Gary · Coaches outing ☔ 45% rain
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💼 Year 2 with Gary
Sky-blue vest finds its home here — Def Leppard tee + black wide-leg trousers + Gold Adidas — relaxed but polished for a day with Gary.
Def Leppard teeBlack trousersGold Adidas
Sky-blue vestBlack trousersPink AdidasStriped scarfDino pack🍸 Coaches Outing (evening)
Floral dress second appearance — different context, different week. Tan bag works better here than the leopard with this palette.
Floral dressDenim jacketBlack flatsTan bagWednesday Retreat
Lunch w/ Calvina · Welcome Reception @ Pia's ☔ 35%
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🥗 Lunch
Denim jacket over black tank + cropped jeans — casual-cool for lunch. Clean and easy.
Black tankDenim jacketRipped jeansBlack flats🐆 Welcome Reception — First Impression
Leopard on leopard — you either commit or you don't. You're committing. The denim jacket grounds it and keeps it from going too precious. This is a memorable first impression for the retreat crew.
Leopard dressDenim jacketPink AdidasLeopard bagThursday Retreat
Main Retreat Day · Watertower Dinner
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🔥 Main Retreat Day
All-black anchored by the tan belt. Sleek and powerful for your biggest retreat day. The vest gives structure without formality.
Black tankBlack vestBlack trousers
Tan beltBlack flatsTan bag🍷 Watertower Dinner
Red dress + pink belt + gold Adidas is a creative, WOW-cool look — not trying to be fancy, just interesting. The denim jacket seals the "I know what I'm doing" energy. The tan bag keeps the warm palette cohesive without competing with the red.
Red dress
Pink beltDenim jacketGold AdidasTan bagFriday Retreat
Retreat Day 2 (outside) · VIP Evening ✨
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🌤 Retreat Day 2 (outdoor)
Comfortable, practical, and the rust/earth tone palette is cohesive with the olive. Olive gets its third day of work here.
Rust tankOlive jacketBlack joggersGold Adidas✨ VIP Evening — The Fish Vest Moment
The fish vest is your most distinctive piece and VIP evening is when the most new people will be watching you. Comfortable, creative, and completely Brooklyn-coded. Last year: fur coat. This year: fish. The theme continues.
Black tank
Fish vestBlack trousersPink AdidasStriped scarfDino packSaturday Retreat
Bathhouse · Lunch · Coaches Workshop
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🛁 Bathhouse
Red Birkenstocks🍜 Lunch
Post-bathhouse cozy. The red Birkenstocks pop against the neutrals.
Ivory tankBrown pulloverBlack joggersRed Birkenstocks📋 Coaches Workshop (if separate)
Quick change if needed. The skirt dried fast from any hand-washing earlier in the trip.
Gray teePleated skirtSunday
Comfy travel home ✈
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✈ Travel Home
Cozy, pulled-together, and you'll arrive home looking like you weren't destroyed by 11 days of NYC.
Gray teeBrown pulloverBlack joggersGold AdidasTan scarf
