Why it’s harder to pack for 3 days vs. 3 weeks.


As you have probably noticed, I’ve been traveling a lot this year. When I say a lot, what I mean is that I’ve been out-of-town 3 out of 4 weekends a month for the past 6 months.


Turning 30 means I’ve officially entered into what is commonly known as the second wave of wedding seasons. Between bachelorette parties, bridal showers and destination weekends, my free time has been taken over by shopping for, planning for, packing for and unpacking from a constant stream of 3 to 5 day trips.


It’s not that I’m complaining, these short jaunts have been a welcome reprieve from the extensive planning that goes into a 1 to 3 week vacation.  I take smaller yet more consistent chunks of time away from work and, in turn, feel far less burn out than usual. And honestly, who really needs more than 5 days in Hawaii? But here is the thing I didn’t quite expect – packing for 3 to 5 days is much harder than packing for a month away. Let me explain…


  1. I’m now traveling with a man. Yes, a man who thinks that bringing any bag larger than a weekender is considered over-packing. It doesn’t matter if the trip is for 2 nights or 2 weeks, he will still pack a barely full carry-on with three outfits inside. You would think that after a year and a half together I would get over my need to appear low maintenance and spontaneous yet also always impeccably and appropriately dressed. Alas, no, I will forever obsess about being prepared for every possible last-minute situation he could throw at me. “Surfing lessons? Beach volleyball tournament?” “Why yes, I have the perfect bikini that won’t fall off or ride up and it just happens to be lying here” …..”Last minute drinks with my business contact you’ve never met that happens to be vacationing here with his wife?” “I’d love to, let me just throw on that fashionably artistic yet conservative shift dress I packed last minute.” You can see where I am going with this.
  2. I may be a bit OCD when it comes to dress codes. I’ve found that most people simply want to be sure they don’t look like they are “trying too hard” or are “inappropriately dressed” for events; I, on the other hand, have a full checklist of requirements. I’d prefer to be over-dressed to under-dressed — I can blame my Italian grandmother for that. I’m sure that my therapist would tell you it’s my way of countering the anxiety I feel in new social situations. You know the drill, obsess over the elements you can control because you have no influence over the rest of it.
  3. Method traveling. We can talk more about this concept at a later date but in summary it is the term my sister coined for my obsession with character dressing while I travel. I have always thought of my life as a series of short scenes from a movie and myself as the heroine (as well as the costume designer of course). “What would my character wear as she sauntered through a marketplace in Barcelona?”… “And what about when she first sees him across the cafe sipping espresso?”… “What dress is she wearing, standing on the cliff of a beach wedding, that perfectly swirls around her as the wind catches it?” My character clearly has a consistent sense of style and individuality but she fully emerges herself into each experience. In my opinion, her (my) wardrobe should reflect that. And, let’s be honest, it makes for some beautiful photos. My therapist would also have plenty of thoughts on this one, but I’ll stick with my theory that I’ve always had a penchant for the theatrical, even if it’s only in my mind.
  4. Ok, it really is ridiculous to pack more than a small piece of luggage for a weekend away. Smaller suitcase equals less space equals tighter editing. Gone are the days of having 3 outfit options for every occasion as well as a few extra pieces “just because there is extra room.” I’ve learned to edit, to commit to my outfits beforehand and yes, I’ll say it, to pack less shoes. I’ve finally excepted that shoes are the killer of a perfectly packed suitcase.


So after countless weekends away, I feel as if I have almost perfected the art of the short-term, condensed packing. And because I would like to save you all from the hours of Pinterest scrolling, Google searching and Facebook stalking of your most stylish friends, I’ve decided to breakdown some of my recent trips into outfits and corresponding events. I’ll leave the rest up to you.


Note: Yes, I’ll fully admit that I have searched the hashtag #weddingseason to determine what’s appropriate to wear for various events. 


I hope you enjoy and safe travels!

💋 Brooks

Weekend Guide / Point Reyes