Hawaii Outfit Planning

Our vacation is finally here! Man BFF and I are jet-setting to Hawaii on Sunday! Lucky for me I have the day off, so I’ve been planning my outfits all day while Man BFF has been slaving away in his home office. Since I usually take a lot longer to pack, I figured I would take the afternoon and pull my Hawaii fits together. I took pictures of them to (a) post on my blog, (b) remind myself what accessories go with what outfit, and (c) have a reference for Man BFF to pack appropriate outfits that match my level of casualness or fanciness by occasion.

Flight to Hawaii

I think the ultimate venue for celebrity style is the airport. So, to mimic my girl Kourtney, I’m planning to wear a casual striped blazer and flats for a pulled together comfy look.

Haleakala National Park

My idea of a Hawaiian vacation is Mai Tais at the pool, but since Man BFF is volcano-crazay, our first day in Maui will be spent at Haleakala National Park looking at some volcano crater. Wearing sneakers is not the ideal situation, but I figure we’ll be hiking so I might as well plan accordingly.


After volcano-trekking, Man BFF and I are headed to a luau. I wanted to wear something very colorful and this dress has been a great asset over the last few years for weddings, summer parties, and the like.

Dinner at Ko

On Tuesday, we’re spending the morning driving the Road to Hana which is a gorgeous route around Maui where you can stop to swim, take pictures, and enjoy the lushness that is Hawaii. That afternoon I’m hoping to get some pool/Mai Tai time in, and then that evening will be spent eating dinner at our hotel, the Fairmont Kea Lani. This is a very special outfit becuase I bought the dress on our honeymoon and the pearls were a wedding day gift from Man BFF.


Doing this blog post made me realize I have no planned outfit for Wednesday! Eek, I’ll need to work on that. Wednesday morning we’re taking a canoe ride in Maui before taking a short flight to Oahu for the next few days!

Pearl Harbor Tour

On Thursday, we’re getting picked up bright and early by a tour company to tour Pearl Harbor and then spending the rest of the day at Waikiki beach, or taking a hula class if I get my way.

Dinner at Morimoto

For our last night in Hawaii, Man BFF and I have reservations at THE Iron Chef’s restaurant. We’re looking forward to the freshest sushi we’ve ever tasted!

Flight Home

This will be a sad day. Man BFF and I had a friend over for dinner the other night who said she literally cried on the way to the airport when leaving Hawaii. Well, I may be sad, but at least I’ll be comfortable for this overnight flight with leggings and flats.


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