One Trip, Two Outfits: Chic Ensembles for a Spring Vacation

A few days ago, I was approached by travel expert Kendra Thornton about an opportunity to create a style board as inspiration for her upcoming family vacation to Downtown Disney. I was beyond excited about the chance to work with Kendra, who’s been featured on both Tyra Banks and Nate Berkus’s talk shows, and couldn’t wait to get started on her “Kendra’s Night Out” Challenge!

I’ve never been to Downtown Disney myself, but I’ve been to Orlando quite a few times and know that it’s full of not only families making fun memories that will last a lifetime, but also gorgeous and on-trend ladies who like to vacation in style. That’s why I wanted to make sure to give Kendra a pair of outfit ideas that were casual enough to enjoy some fun with her family, but chic enough to stand out at the delicious restaurants and amazing shops that abound in Orlando.

Keep reading for a note from Kendra below—where she’ll fill you in on her upcoming trip and all the excitement it entails—and then check out the style boards I’ve created to help Kendra take Downtown Disney by storm (and in style!).

Kendra’s Fashion Challenge is about to hit Downtown Disney! Finding the perfect fashions for my night out with my husband & three kids is quite the challenge! I could really use some help putting together the best outfits for Orlando. I am 40 years old and ready to hear the best fashion advice from my favorite bloggers. Help me find an outfit that will complement my family’s night out! I want to look my best on my best. I will be surrounded by the people I love and enjoying an once-in-a-lifetime experience.

One of the things I look forward to on my trip is the House of Blues. The Downtown Disney location is very lively, even during the day and on the weeknights. It’s upbeat, and live music is always playing. The menu features some of the best BBQ in the area, so I am sure the kids will love it. Even if I don’t get to see a famous band perform, I am always up for some dancing after a tasty meal. I really look forward to the all-American style at the House of Blues!

Having the right outfit could make or break my trip to Orlando. The city is full of sophisticated people enjoying a world-class resort. I look forward to seeing some of the more relaxed areas of the large city, as well as Downtown Disney. Orlando is full of exciting opportunities to bond with family over activities, delicious dinners and unique shopping. No matter what you look forward to the most during your trip, looking good Downtown Disney is a must. Having the right outfit will make the night one to remember for a lifetime.

Ready to see what I’ve come up with to help Kendra transition from days in Downtown Disney to nights on the town? Check out my outfit ideas below:

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1. Nail polish in “Trallop” by Butter London 2. Collar necklace by First People First 3. Sunglasses by Ray-Ban 4. Watch by Michael Kors 5. Felt hat by Brixton 6. Tote by Tory Burch 7. Lipstick in “Coral Ribbon” by Lancome 8. Heeled sandals by Loeffler Randall 9. Lace shorts by Alice + Olivia 10. Printed blouse by Vivienne Westwood 11. Crystal necklace by T+J Designs 12. Link bracelet by Juicy Couture

Lace shorts are such a delicate, feminine and on-trend way to stay cool and comfy while out and about, and I love the idea of pairing them with a bold, floral, lightweight blouse to brighten things up a bit. To keep things casual enough for a day of strolling around shops, restaurants and other exciting sites, I highlighted the ensemble with simple ankle-strap sandals; gilded, layered jewelry; and a spring-ready woven tote. Finishing the look with bright lips, nude nails, and a floppy hat and sunglasses to protect from the blazing sun, this would be the perfect outfit for spending a day with the family at Downtown Disney and the surrounding areas.

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1. Scuba dress by Josh Goot 2. Statement necklace by River Island 3. Folded clutch by Clare V. 4. Lipstick in “Alibi” by Topshop 5. Cocktail ring by Kenneth Jay Lane 6. Eyeshadow quad in “Bronze” by Bobbi Brown 7. Gold bracelet by Michael Kors 8. Wedges by Tory Burch 9. Stud earrings by Kate Spade New York

Kendra mentioned that she can’t wait to visit the House of Blues, fill up on some tasty barbecue and then dance the night away in the evening, so I wanted to give her an outfit that was comfortable and easy to move in, but still ultra-chic and statement making. The bright orange dress is practically made for a spring evening on the town, and it’s just screaming for an eye-catching necklace to add some more visual appeal. Since the dress and necklace are bold choices on their own, I decided to anchor the look with simple shoes and accessories, along with gold baubles and neutral makeup.

For me, these two outfits are totally ideal for a stylish vacation in always-sunny-and-cool (but never cold!) Orlando, but what are your thoughts? What you would you wear for a chic Disney getaway?

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2 thoughts on “One Trip, Two Outfits: Chic Ensembles for a Spring Vacation

  1. The outfits are absolutely beautiful, but I take issue with some of your selections. Spending a day on heels will mean limping and no dancing by evening. The wood-block heels also have zero cushioning (cork is better). Instead, how about a pair of stylish gladiator flats with good support? A cross body bag is a more practical selection for touring, especially if you are carrying it around all day. The over-the-shoulder strap allows for hands-free touring. A bag with clip-on convertible straps means you can choose between handles or over the shoulder. A cute skort is a nice girlie alternative to shorts. A longer short might also be better for all-day walking. It keeps potential chafing down.

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