Packing Plans: Carrying On for Five Days

Today, the HOTY, Finally Five and I are leaving for New York. I’m super excited!  It will be a combination of work and fun, which is my favorite way to travel!

For as long as I can remember, I have done everything in my power to avoid checking a bag. There is something about the wasted time at baggage claim that makes me batty (and a little cranky!). As a result of not checking a bag, my luggage is never lost and it always magically arrives at my destination at the same time I do (Silver Lining).

I actually think that I would have been more suited to the era of Trunk Travel. I mean, really. Trunks are so elegant and well constructed.  I bought these gorgeous Louis Vuitton suitcases years ago at an estate sale (for a steal, by the way…Boy Oh Boy was I excited!). Now, the thing about traveling with hard cased luggage is that you have to have the strapping man to carry them for you because they are heavy without anything even in them.

So, since I will not be carrying these suitcases, I will manage, as I always do, to schlep through the airport with my trusted rolling duffle bag and tote.

The last time I went to New York with a girlfriend (who always checks her bags, by the way), she was amazed by how much stuff I pulled out of my suitcase, so much so in fact, that she called my bag a “clown car.” I took it as a compliment. Right?!?

For my upcoming 5-day trip to New York…

In my Tote Bag, I will be brining:

  • My cosmetics kit. Fortunately (or not), I don’t wear much makeup. Included will be my 3-1-1 bag.
  • Brush and Hair Styling Goop (i.e, gel)
  • Tamoxifen because I can never leave home without the darn stuff.
  • MacBook Air, iPad and iPhone…clearly I’m an Apple kind of gal.
  • Pashmina…because I am either freezing or hot flashing on planes and if I happen to be a remotely comfortable temperature, then it serves as a snuggly pillow!
  • Book and magazines
  • Wallet
  • Sunglasses…you wouldn’t believe how many times I’ve forgotten my sunglasses on trips that require a pre-dawn departure.

In my Carry-On, I will be bringing

  • 3 pairs of pants, including one pair of jeans
  • 2 jackets, including one leather one that I can dress up or down and will keep me warm
  • 2 skirts
  • 1 white T-shirt. I’m kind of obsessed with the J.Crew Tissue T-shirts right now.
  • 1 white blouse
  • 3 cashmere cardigans (one black-that I will wear on the plane, one cream, and one in a bold color)…I especially love my Jules Allen cashmere sweaters. She is as adorable in person as are her sweaters, by the way!
  • 1 simple shift dress that I can wear under the jackets
  • 3 pairs of shoes, including a pair of flats that I will wear on the plane
  • 5 pairs of undies
  • 5 pairs of gym socks
  • 2 pairs of black tights (because it’s cold in New York and my blood has thinned since living in California!). My all-time favorite tights are the Wolford Black Velvets. They are pricey (about $40), but the Silver Lining is that one pair lasts for a couple of years. Seriously. They are that great.
  • A small jewelry holder containing a few distinct pieces to dress an outfit up or down
  • 1 clutch for evening
  • 2 pairs of lightweight jammies
  • Gym clothing, including my running shoes and 2 pairs of Lululemon pants and one Lululemon jacket
  • Chargers for my MacBook Air, iPad and iPhone as well as an extra camera battery. I can separate them because I am NOT checking my bag. Love that.
On the plane, I will be wearing
  • Black pants
  • White blouse
  • Cashmere cardigan
  • Coat
  • Flat shoes
  • Colorful scarf
With that I will bid you adieu for now, but will be in touch from New York!
The real voyage of discovery consists not in seeing new landscapes, but in having new eyes.
– Marcel Proust

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  1. Adrienne says

    Oh my goodness , I would love to look at all of those magical store windows thru Finely Five's eyes ! Have a wonderful time ! Adrienne

  2. Kim C says

    Great the list of clothing and accessories! Perfection! You must have borrowed Mary Poppins duffle bag!
    Have a wonderful time. You especially, Finally Five…enjoy the Christmas Magic!

  3. Catie says

    How great, you HAVE to show me how to pack like this, as this is NOT my talent, and I am a serious traveler!! Just got back from Thanksgiving in NYC with the family, it was beautiful up there!! Have a great trip! 🙂

  4. Lesley Sutton says

    The obvious next question is "what brand of rolling tote lets you get all of that in it and still fits in the overhead?" I am impressed Hollye! And completely envious of 5 days in NY at this time of year – lovely.

    • says

      Great question, Lesley. It is an old Prada bag with two side zippers and a top zipper (by the handle). I've had it for 10+ years. Definitely worth the investment. Thanks for your comment!