Packing for My Winter Escape (and Tips That Make It Easier)
Hello from my Winter escape.
I come to the same Caribbean island every year, during the same weeks, so by now I know exactly what I need, and even the possible weather variations.
Packing has become very easy. I bring many of the same pieces year after year, usually adding just a couple of new items that I bought during the previous months.
I love resort-wear dresses, but I always bring light pants and shirts with sleeves as well. We usually have a few windy evenings, and having those options makes a big difference.
For this trip, I created outfits in the styling app that I use with my clients, and for myself, too. These are real pieces that I own, and having everything organized digitally allows me to access my outfits on my phone anytime.
This is exactly what I do with clients: I create outfits for work, business trips, vacations, or special occasions so everything feels easier and more intentional. And honestly, if I take the time to do this for myself, it means it truly helps.
Below you’ll see some of the outfits I planned for this trip.
Tips That Help Me Pack (for This Trip and in General)
1. Try everything before you pack.
Especially pieces you haven’t worn in months. It prevents surprises and helps you feel confident about what you’re bringing.
2. Think about versatility.
Consider how one piece can work in multiple ways. For example, this handmade crochet dress doubles as a dress, a third piece, and a beach cover-up.
3. Choose a color palette.
This makes mixing and matching much easier. For shorter trips, neutrals plus two colors work well. For longer trips, neutrals plus three colors give more variety.
4. Be realistic about shoes.
I rarely bring high heels unless I know I’ll need them for a specific event. This time, I brought low wedge sandals, which worked perfectly with my patterned pants.
5. Keep jewelry intentional.
Jewelry doesn’t take up much space, but it can become heavy if you bring too much. A few versatile pieces are enough.
6. Simplify bags.
I brought two small bags and one beach bag, the same one I used as my personal item on the plane.
7. Keep makeup minimal.
At the beach, I don’t do much. A tinted moisturizer with SPF works for day and night, plus a creamy blush that doubles as lipstick. Lately, I’ve been wearing Jones Road a lot.
Packing becomes much less stressful when you plan outfits ahead of time and choose pieces that work together easily.
I hope these ideas inspire you for your next trip.
If you want help planning outfits for travel or organizing your wardrobe digitally like this, we can always explore that together.
Hi, I’m Marcia Crivorot, a Personal Stylist based in NY. Once a month, I send newsletters featuring style tips, recommended brands, and a shopping guide. Unlock previous editions of my newsletters and receive my emails firsthand by subscribing.
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