Well Planned · Lookbook
Michelle's Calistoga, CA Trip
October 2–4, 2026 · Calistoga, CA · Essentials (3 outfits) package
Here's what we're recommending for Michelle's trip:
- Three looks — a dinner outfit, a hiking outfit, and a wine tasting & picnic outfit — each with an Under Budget, On Budget, and Splurge option so you can choose the mix that works best.
Every item below is currently verified in stock in your size (top XS, bottom XS, shoe 6.5), in the pictured color, with a real product photo.
Look 1 · 50th Birthday Celebration Dinner at Solage
Dressy, Not Fussy
Elevated enough for a wealthy-crowd dinner, easy enough for a California evening — a maxi dress with a low, walkable heel.
Under Budget
Total $89.97
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Dress
Big Entrance Floral Maxi Dress
$45.00Size Small · in stock
A sleeveless scoop-neck maxi with a smocked waist.
View product — Big Entrance Floral Maxi Dress (opens in a new tab) -
Shoe
Everess Square Toe Mule
$44.97Size 6.5 · in stock
A low wedge — goes with everything.
View product — Everess Square Toe Mule (opens in a new tab)
On Budget
Total $167.95
-
Dress
Kinleigh Red Multi Abstract Pleated Bustier Maxi Dress
$98.00Size XS · in stock
Vibrant, pleated maxi.
View product — Kinleigh Red Multi Abstract Pleated Bustier Maxi Dress (opens in a new tab) -
Shoe
Rania Square Toe Heeled Sandal - Black
$69.95Size 6.5
A black colorway that pairs cleanly with the colorful dress.
View product — Rania Square Toe Heeled Sandal - Black (opens in a new tab)
Splurge
Total $208.00
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Dress
Anabelle Halter Neck Maxi Dress
$109.00Size XS · in stock
Fun and floral on a navy ground, sleeveless with a smocked bodice and relaxed A-line skirt.
View product — Anabelle Halter Neck Maxi Dress (opens in a new tab) -
Shoe
Mylee Heels — Black Leather
$99.00Size 6.5 · in stock
Gold hardware accent ties into your gold jewelry preference; tan still reads well against navy florals.
View product — Mylee Heels — Black Leather (opens in a new tab)
Look 2 · Saturday Hike at Bothe-Napa Valley State Park
Cute, Weather-Ready Layered Athleisure
You're bringing your own hiking shoes, so this is your top, layer, bottom, and sun hat — every tier includes both a short-sleeve base and a long-sleeve layer for the cool morning start.
Under Budget
Total $53.97
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Top
Fluid Seamless Fitted T-Shirt — Heather Gray
$14.99Size XS · in stock
Sweat-wicking short-sleeve base layer for a 2-hour hike.
View product — Fluid Seamless Fitted T-Shirt — Heather Gray (opens in a new tab) -
Layer
Fluid Seamless Fitted Long Sleeve Top — Medium Grey
$17.99Size XS · in stock
An easy long-sleeve layer to pull over the tee if the morning starts cool.
View product — Fluid Seamless Fitted Long Sleeve Top — Medium Grey (opens in a new tab) -
Bottom
High-Waisted PowerSoft Full-Length Legging — Black Jack
$20.99Size XS · in stock
Reliable everyday hiking legging, easy to layer under shorts if it warms up.
View product — High-Waisted PowerSoft Full-Length Legging — Black Jack (opens in a new tab) -
Accessory
Black Trucker Hat
$0.00Size
Bring your own!
View product — Black Trucker Hat (opens in a new tab)
On Budget
Total $181.97
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Top
Everyday Soft Racerback Tank Top — Navy Blue
$30.00Size M · in stock
An athletic tank in navy, a step up in performance fabric from Under Budget's tee.
View product — Everyday Soft Racerback Tank Top — Navy Blue (opens in a new tab) -
Layer
Sandwash Crop Pullover — Dark Khaki Olive
$23.97Size XS · in stock
A quarter-zip crop pullover in Dark Khaki Olive, a warm layer that keeps this tier well under budget.
View product — Sandwash Crop Pullover — Dark Khaki Olive (opens in a new tab) -
Bottom
Momentum Balloon Pants — Dried Palm
$128.00Size XS · in stock
A relaxed, wide-leg balloon pant in an earthy Dried Palm green — breathable and roomy for the trail with a little more personality than a basic legging.
View product — Momentum Balloon Pants — Dried Palm (opens in a new tab) Accessory
Wear your own accessory
Splurge
Total $289.97
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Top
Sandwash Sleeveless V-Neck Popover Shirt — Darker Ardosia Slate
$68.00Size XS · in stock
A structured sandwash popover in a deep navy slate, an easy neutral that layers cleanly under the stone puffer jacket for a hike.
View product — Sandwash Sleeveless V-Neck Popover Shirt — Darker Ardosia Slate (opens in a new tab) -
Layer
Canyon Insulated Jacket — Pumice
$111.97Size XS · in stock
One long-sleeve puffy layer in a light, neutral stone color, full-zip with recycled Primaloft insulation.
View product — Canyon Insulated Jacket — Pumice (opens in a new tab) -
Bottom
Sandwash Wide Leg Pant — Darker Ardosia Slate
$98.00Size XS, Regular inseam · in stock
A wide-leg sandwash pant in the same Darker Ardosia Slate as the top, comfortable knit with room to move on the trail.
View product — Sandwash Wide Leg Pant — Darker Ardosia Slate (opens in a new tab) -
Accessory
Packable Straw Down Brim Hat - Shade & Shore Tan
$12.00Size One size · in stock
Wider brim, more sun coverage — also worn wine tasting.
View product — Packable Straw Down Brim Hat - Shade & Shore Tan (opens in a new tab)
Look 3 · Wine Tasting & Picnic at Tres Sabores
Elevated Casual, Outdoors All Afternoon
Comfortable enough for a 1.5-hour outdoor picnic and tasting right after your hike — shorts instead of pants for the warm Calistoga afternoon, and no heels on the vineyard's grass and gravel.
Under Budget
Total $95.98
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Top
100% Organic Cotton Gauze Roll Sleeve Shirt — White
$11.99Size XS · in stock
Easy cotton tank.
View product — 100% Organic Cotton Gauze Roll Sleeve Shirt — White (opens in a new tab) -
Bottom
100% European Linen Shorts — Chambray Stripe
$32.00Size XS · in stock
A soft Chambray Stripe linen short that pairs well with the gauze top.
View product — 100% European Linen Shorts — Chambray Stripe (opens in a new tab) -
Shoe
Laws Toe Loop Flat Sandal — Tan
$39.99Size 6.5 · in stock
A cushioned faux-leather slide with an adjustable buckle — good footing on the vineyard's grass and gravel.
View product — Laws Toe Loop Flat Sandal — Tan (opens in a new tab) -
Accessory Same as Under (Hike)
Packable Straw Down Brim Hat — Tan
$12.00Size One size · in stock
View product — Packable Straw Down Brim Hat — Tan (opens in a new tab)
On Budget
Total $151.80
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Jumpsuit
100% Organic Cotton Gauze Smocked Wide Leg Jumpsuit — Indigo Blue
$49.90Size XS · in stock
A smocked, wide-leg jumpsuit in indigo blue — an easy one-piece look for wine tasting and the picnic that keeps this tier close to budget.
View product — 100% Organic Cotton Gauze Smocked Wide Leg Jumpsuit — Indigo Blue (opens in a new tab) Bottom
No bottom with this look — the jumpsuit covers it.
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Shoe
Farrin Block Heel Sandal — Buff Tan/Cyprus Tan
$89.90Size 6.5 · in stock
A low block-heel sandal in a warm tan tone that pairs with the indigo jumpsuit.
View product — Farrin Block Heel Sandal — Buff Tan/Cyprus Tan (opens in a new tab) -
Accessory Same as Under
Packable Straw Down Brim Hat — Tan
$12.00Size One size · in stock
View product — Packable Straw Down Brim Hat — Tan (opens in a new tab)
Splurge
Total $316.99
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Top
Rowe Rib Scoop Tank
$38.00Size XS · in stock
A muted tan-and-white stripe in Italian superluxe fabric.
View product — Rowe Rib Scoop Tank (opens in a new tab) -
Bottom
Brooke Gingham Linen Maxi Skirt
$110.00Size S · in stock
A best-selling gingham maxi skirt with a soft feel and easy smocked waistband.
View product — Brooke Gingham Linen Maxi Skirt (opens in a new tab) -
Shoe
Wink Sandals — Bone Leather
$39.99Size 6.5 · in stock
An essentially-flat sandal (0.5" sole) — no heel for the vineyard's grass and gravel.
View product — Wink Sandals — Bone Leather (opens in a new tab) -
Accessory
Helena Packable Straw Sun Hat — Tan
$129.00Size One size · in stock
Also worn on your hike.
View product — Helena Packable Straw Sun Hat — Tan (opens in a new tab)