Sunset Wandering…

While I tend to procrastinate many things (especially house cleaning! ?), packing is not something I like to leave to the last minute. Generally, I start thinking about what to bring at least two weeks before my trip, sometimes more. I need to consider what we’ll be doing, what I want to wear, and—most importantly—how I want to feel.

Planning Ahead: Dressing for the Destination

When we went to Italy, for example, I knew I wanted to wear stylish blue-and-white dresses with sparkly sandals. Luckily, that was the trend that year, and I loaded up on a bunch of cute outfits that suited my curated vibe perfectly.

For beach vacations, my suitcase is basically a rolling dress rack:

• Simple, casual dresses for breakfast and lunch
• Cover-ups that double as day outfits
• More elegant dresses for dinners at the a la carte restaurants

Poland, however, was another story. I knew it would be cooler and possibly rainy. Since we had plans for day trips that included lots of walking, I packed versatile layers and comfortable clothes. To blend in with the Polish aesthetic, I leaned into black and neutral separates that I could mix, match, and dress up or down.

Of course, I turned to Amazon for a few essentials: a packable raincoat and a black maxi dress that could take me from wandering around old towns to dinner by the river.

And then there’s the wildcard factor—weather! The trip started cool and rainy but ended with temperatures soaring into the 30s. Luckily, Warsaw has fantastic shopping malls, and I scored a couple of breezy summer dresses on end-of-season sales.

Shoe Strategies (and Mishaps)

Shoes can make or break a trip. For Italy, I brought a pair of white Vessi sneakers. They were super comfortable—until I hiked up Mount Vesuvius and walked Rome’s cobblestone streets. Being waterproof, they were almost impossible to clean afterward, and after a few washes, they stayed a sad grey. (I’ve since painted them purple and now wear them for errands. Win-win!)

Poland required a more thoughtful shoe lineup. Since it was a “home away from home” trip with a mix of sightseeing, coffee dates, forest walks, and quick overnighters, I packed:

• Running shoes
• Black ankle-strap wedge sandals (which I thought I’d wear)
• Flat sparkly sandals
• White leather platform sneakers (worn on the plane)

The wedges turned out to be a bust—they hurt too much—so I grabbed a cute pair of black leather sandals locally (half-price and comfy right out of the box). Pro tip: leave a little room in your suitcase for spontaneous finds!

For side trips, I packed an empty carry-on and used it just for those mini-getaways. That strategy worked beautifully.

My Actual Packing Process

Now, despite all this planning, I’ll admit my packing method is not Instagram-worthy. I don’t use packing cubes, and I’m not a strict roller-or-folder. Instead, I:

• Lay my clothes gently in the suitcase (half-folded, half-rolled—whatever works in the moment)
• Double-bag liquids, wrapping them in a hand towel just in case
• Use the suitcase’s net compartment for underwear, socks, and swimsuits
• Slip delicate items into a reusable shopping tote to prevent snags
• Tuck shoes into compartments or reusable bags
• Use the hotel’s plastic laundry bag for dirty clothes (especially smelly socks!)

It’s not the most polished system, but it works for me. And yes, I always overpack. I like having options, and I’ve accepted that I’ll never be the type who travels with just a carry-on—unless it’s for a quick weekend.

What About You?

So that’s my approach: a mix of early planning, outfit mood-boarding, and a packing style that’s more ad hoc than minimalist.

Tell me in the comments:

What’s your packing style? Do you swear by packing cubes, or are you a fellow “organized chaos” traveler like me?