Museum Date and Cooking Class
An air-conditioned museum and a hot kitchen call for opposite sartorial approaches, but aspects of the outfits you'd wear to them can be combined. Start with a base of high-waisted denim shorts and a striped T-shirt. Pack a light sweater for the fierce museum AC and tie on a neck scarf for some color. When you head to your class, switch the sweater for an apron; the scarf can now be used as a headband to keep your hair out of your face. Comfortable espadrilles will also be key for a day spent on your feet.
- Waist-Belt Tie Denim Shorts, $78, pixiemarket.com.
- Mixtape Tank Top in Stripe, $45, madewell.com.
- Jazzlyn Espadrilles, $20, asos.com.
- Salt and Pepper Cotton Top, $68, topshop.com.
- Jelly and Cake Apron, $35, thornbackandpeel.co.uk.
- Backpack with Top Handle, $363, mywalit.com.
- Striped Bandana-Style Scarf, $13, zara.com.
Champagne Brunch and Outdoor Movie
Looking pulled together for a celebratory champagne brunch when you're planning on spending the evening outside is one of the easier activity combinations. Dress up for your first stop with fun floral trousers, a flowy top, and a choker. When it cools down at night, you'll be glad you opted for pants. At the movie, break out a sweater with a bright pop of color and Turkish towel (lighter and thinner than a regular blanket) to sit on during the movie. You can always slip off the slides to get more comfortable.
- Floral Print Trousers, $50, zara.com.
- Margarita Off-the-Shoulder in Cream, $275, apieceapart.com.
- A-Line Jumper, $89, cosstores.com.
- Luxe Cat-Eye Acetate Sunglasses by Le Specs, $125, net-a-porter.com.
- Double Spear Collar, $105, melroso.com.
- Agnes Backpack, $535, clarev.com.
- Fouta Beach Towel, $48, serenaandlily.com.
- Leather Mule Sandals, $33, asos.com.
Farmers' Market and Outdoor Dance Performance
Stay cool at the farmers' market with relaxed pants and a loose T-shirt. Get a pop of color from this straw bag, which is big enough to hold both your market spoils and a pashmina to keep you warm during the dance performance.
- Striped Popover Sweater, $85, jcrew.com.
- Geremia Trousers by Weekend Max Mara, $150, matchesfashion.com.
- Straw Wide-Brim Fedora by Rag & Bone, $225, blueandcream.com.
- Ibiza Tote by Mar Y Sol, $135, bloomingdales.com.
- Leonard Mirrored Lense Sunglasses in Tortoise by Illesteva, $178, intermixonline.com.
- Tie-Leg Jelly Sandal, $17, asos.com.
- CK Logo Pashmina Scarf, $35, calvinklein.com.
Afternoon Picnic and Outdoor Yoga Class
Dressing for activities that range from lounging in the grass with your friends to vinyasa in the park is simple when you can just throw on a loose dress and wear your yoga clothes underneath. Best of all, the mat can double as a picnic blanket!
- Striped Tunic, $50, zara.com.
- Cinger Hi-Top Trainers, $45, topshop.com.
- Energy Bra Exhale, $58, shop.lululemon.com.
- Groove Short II, $48, shop.lululemon.com.
- Embossed Yoga Mat by Adidas by Stella Mccartney, $59, stylebop.com.
Road Trip to a Hiking Trail and the Beach
For a day-long adventure that entails a driving to your outdoorsy destination, dress in layered basics. Start the day by pulling on a sweatshirt over your T-shirt and shorts to stay warm in the car. Once you embark on your hike, the oversize shirt will be perfectly loose and cool, and will also double as a beach cover up when you shed your shorts by the sea. Also versatile: the fun printed scarf, which can serve as a towel both on the trail and at the beach.
- The Kanken Mini, $60, fjallraven.us.com.
- Juvenate Sneaker by Nike, $85, nordstrom.com.
- Cold Dye Linen Shirt by & Other Stories, $45, stories.com.
- Ripped High-Waisted Denim Shorts by River Island, $46, asos.com.
- Cropped Sweatshirt by Astraet, $179, farfetch.com.
- Macramé Trim Bikini Pant, $26, topshop.com.
- Plain Baseball Cap, $13, asos.com.
- Mesh Bikini Crop Top, $26, topshop.com.
- Printed Scarf, $40, mango.com.
Music Festival and a Family Dinner
OK, so you have festival tickets the same day as your family reunion dinner—no big deal! A fun floral dress is just as good for dancing as it is for dressing up. Think ahead and pack a gold choker, sleek slides, and a bright sweater to freshen up in the evening.
- Quay Fleur Round Cat-Eye Sunglasses, $45, urbanoutfitters.com.
- Hambledon Floral-Print Silk Georgette Maxi Dress, $520, net-a-porter.com.
- Wide-Brim Flat Top Hat, $278, needsupply.com.
- Stan Smith Sneakers by Adidas by Raf Simons, $258, farfetch.com.
- Phoebe Choker, $38, baublebar.com.
- Fringe Flap Faux Leather Backpack by Street Level, $54, nordstrom.com.
- Flat Shoes with Metal Heel Detail, $30, zara.com.
- Cotton Jackie Cardigan Sweater, $50, jcrew.com.
Ceramic Class and Rooftop Dinner Party
Denim dungarees are the unsung day-to-night hero: Don't worry about sullying your party dress at a ceramics class—instead, wear these overalls and add a silk scarf and an elegant cardigan for dinner.