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what happened when I ignored all of my own packing advice

what happened when I ignored all of my own packing advice

my contribution to the plethora of substack summer packing posts

Dacy Gillespie's avatar
Dacy Gillespie
Jul 15, 2025
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what happened when I ignored all of my own packing advice
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Something you should know about me is that I'm one of those annoying people who takes pride in packing light. I hate dragging luggage around, I don’t like to check bags, and for the last ten+ years, we’ve also had child paraphernalia to deal with (only recently have I had a whole suitcase to myself!). Packing light1 has always been a priority and I’ve accepted that I will not be my most stylish self while traveling.

However, as my style evolves, my views around other areas of my wardrobe evolve as well. For a recent trip to visit family, I thought I might experiment a bit with *not* bringing the absolute fewest number of clothing items. Here’s my packing process for a trip a couple of weeks ago to visit my family in Mobile, Alabama and my own advice I did or didn’t take.

Advice taken: plan ahead

I have too much anxiety to not follow this one. I always pull out a bunch of options a couple of days in advance. Usually I use a wardrobe rack, but ours is currently full with winter coats, so I just hung things on my closet doors. I’m a visual person, so it’s really helpful for me to see everything together to make sure that I can make multiple outfits from what I bring.

Advice not taken: don’t buy anything new before a trip

I always start with more than I’ll need and then start to whittle it down. As I was doing this, I decided that I needed a new dress immediately. In my defense, I had been wanting to add a colorful dress for hot weather (I only had one) and had been looking in a thoughtful and intentional way, but by that point I hadn’t found anything. I threw up my hands and went to Marshall’s, where I found a very cute and comfortable dress that was good for the heat. I wore the dress on my trip and at least 4 times since (you should not do this, last minute shopping isn’t usually this successful!).

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Advice not taken: only bring one extra pair of shoes

This isn’t something I always follow, but usually do for casual summer trips like this one. This time, I thought I might actually like to wear different shoes for different outfits 😯 I brought flip flops and yellow slides, but didn’t end up wearing either of them. The Birks I wore on the plane are just too comfy and easy.

yes, I’m a packing cube girlie

Advice not taken: rewear as much as possible

Because of the heat, I actually packed an outfit per day. My suitcase wasn’t overflowing or anything, so it wasn’t a big deal, but I definitely did overpack. I didn’t get as sweaty as I had anticipated (going from air conditioning to air conditioning), so I did end up rewearing more than a few things and a few items didn’t get worn at all, or very little.

All in all, I probably would have done a little better if I had followed my own advice (except for that dress!). If you realllly struggle with overpacking or just not having a system for getting started, I put all my advice (much more than mentioned here!) into a mini-course with videos, a workbook, and a packing spreadsheet template! Use code SUBSTACK for 20% off.

Behind the paywall: how much I actually packed, the specific items, and how I wore them.

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