Dear Winston
The art of positive uncertainty.
A thoughtfully curated surprise for yourself or someone you adore—delivered when least expected.
"I've taken the liberty of preparing something rather special..."
The Process
How It Works
Three simple steps to invite a little mystery into your life.
01
Choose Your Commitment
Select a budget that feels right. Winston works within your means to find something extraordinary.
02
Help Winston Know You
Optionally connect your Spotify or Instagram. Winston observes your tastes to curate something personal.
03
Await Your Surprise
Sometime in the next 14-90 days, a carefully curated gift arrives. The when is part of the magic.
The Possibilities
What Winston Might Find
Every surprise is unique. Here's a glimpse of the kinds of treasures Winston seeks out.
For the Audiophile
$100 tier"A vinyl pressing of an album that shaped their teenage years, sourced from a collector in Tokyo."
For the Wanderer
$50 tier"A hand-bound travel journal from a Florentine workshop, paired with ink the color of their favorite sunset."
For the Curator
$250 tier"A signed first edition from an author Winston noticed they'd quoted three times on Instagram."
For the Homebody
$100 tier"Artisan coffee beans from a micro-roaster, a ceramic pour-over, and a playlist for Sunday mornings."
Examples are illustrative. Your surprise will be uniquely yours.
Choose Your Investment
Select Your Budget
Every tier receives the same careful attention. The budget simply expands what's possible.
A Thoughtful Token
A carefully selected delight
A Generous Gesture
Something truly memorable
A Grand Statement
An unforgettable experience
The Winston Guarantee
If your surprise doesn't delight you, we'll make it right. Reach out within 14 days of delivery for a replacement selection or a full refund of the gift value. No questions, no hassle.
The Story
Why Winston Exists
We live in an age of infinite choice and zero surprise. Algorithms show us what we've already seen. We buy what we know we want. The unexpected has become... rare.
Dear Winston was born from a simple question: What if someone who truly understood you could surprise you? Not with something random, but with something perfect—something you didn't know you needed until it arrived.
Winston is part curator, part detective, part old friend who remembers the little things. He studies the music you love, the images that catch your eye, the aesthetic threads that run through your life. Then he disappears into the world to find something just for you.
The wait is intentional. In a world of next-day delivery, we've forgotten the joy of anticipation. A gift from Winston arrives unannounced—that's rather the point.
Questions