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When I mentioned that I was booked on an Oceania cruise and trip to Miami, the first question many asked was whether I was going to post my outfits.  I often joke that if I ever write my autobiography, it will be subtitled, Confessions of an Overpacker, but laying everything out and planning each day's outfits really does help me pack smarter.  I think it's especially useful when you're traveling from cold winter weather to a warm and sunny climate.  It's easy to forget something if you haven't worn a certain outfit for a few months.  After I took these photos, I realized I forgot my Marni belt for the Phillip Lim dress and my other strappy Manolo Blahnik shoes.   

The hardest outfit to plan has been what to wear on the plane.  I am thinking I will wear an ivory silk Blythe Blouse and a light cashmere sweater from J.Crew with jeans.  I can remove the sweater when I arrive and throw on sandals that I'll have stowed in my bag.  I think I might have to wear boots to the airport though which is annoying but it's still snowy on the streets in New York. 

My new favorite tee is this striped boatneck tee from J.Crew.  You can't really see it in the photo but the Theory skirt is white eyelet. I am most excited to use my new Chanel wicker bag from Rice & Beans Vintage on this trip!  I also made the necklace by tying five strands of red beads from the outdoor flea market together with ribbon. Total cost $20. My Roger Vivier sandals were my best purchase ever and very comfortable too.  

Probably should have used a flash for this photo but you get the idea of how the J.Crew tee can be worn with jeans and a blazer while I'm in Miami. Everything has to be able to do double duty.

This is my homage to Grace Kelly outfit. I found these citron yellow Manolo Blahnik flats at Barney's recently for only $159.  I later realized that I had a light cashmere cardigan from J.Crew in my closet in the same color.  It might be too matchy matchy but could work with this dress and others if I get chilly. 

It's hard to see this Club Monaco dress but the top drapes and is a short wrap.  I can wear it during the day with a little belt, my Chanel bag and Christian Louboutin wedges or at night with this green satin clutch from J.Crew. 

This olive green dress in another favorite from Club Monaco.  I wear it now with a big black belt and black tights and boots but it will easily transition to warmer weather.  It might look better with the tan Christian Louboutin wedges though.  See why it's good to lay things out!

My purple silk jersey dress from Phillip Lim can also be worn during the day or at night with a little blazer.  It also packs well since it doesn't wrinkle. I just have to remember to pack my Marni belt that I forgot looks great with this dress.  I also have a light black scarf in case it's chilly at night. I obviously packed more clothes but these give you an idea of what I will be wearing.

The most important thing I have to pack for this trip is sunscreen and self tanner.  Estee Lauder Bronze Goddess Tinted Self-Tanner is my absolute favorite.  I've been using it for years. Estee Lauder also sent me bronzer and new products to try while I'm away.  My friend Ann from Kravet gifted me the Clinique sunscreen and after tan product which was so sweet.  I'm always worried about sunscreen breaking out my face so I am going to try La Mer SPF 30 this trip.

La Mer small size products are perfect for traveling and dry cabin air.  I slather myself with the moistering cream and eye balm the entire flight.  I also absolutely love Embryolisse Lait-Creme Concentre moisturizer which is lighter and Dermalogica Daily Microfoliant. 

I also have to remember to pack good hair products like Phytodefrisant and Moroccan Oil in case it's humid.  Definitely don't want Monica in Hawaii hair in Miami!