 Traveling to a cool place this winter? Why wouldn't you? Winter is a great time to avoid the crowds and get discounts on travel. Sounds like fun fun fun until you find yourself having to pack for the trip! Did you know that packing for vacation is most people's LEAST FAVORITE THING TO DO? That's right, it ranks as high as public speaking and going to the dentist on people's hate-to-do-list. And winter travel can be even more challenging with weighty fabrics. So is it possible to pack everything you need to be warm without packing a jumbo suitcase or multiple jumbo suitcases? It’s easy to pack small when you’re taking swimsuits and flip-flops, but jackets? No way. What if I told you it’s possible to have over 20 different cool weather looks in a carry-on? Impossible you say? Prepare to learn my method for the impossibly possible. (Check out the shopping links and video at the end.)
1. Start with the shoes. Nothing is worse than having a blister or aching feet on the second day of vacation because you didn’t take care of them on your first day of vacation. If you’re looking at vacationing in a cooler climate with the potential for wet weather, your shoes need to be considered carefully. Waterproof boots that can be dressed up or down are a good place to start. Plan the looks that coordinate with them. I love a variety of activities on vacation - my last trip included the opera, going to church, running & hiking, with maybe a beach or spa day depending on the weather. You may take an additional 2-3 pairs of shoes that include running shoes, sandals, and another good pair of walking shoes. These 3 pairs that you’re not wearing on the flight all fit in one side of the carry-on. Shoes take up a ton of space so maximize their storage capacity by putting socks, belts, and underwear in a zip-lock bag inside the shoes. Pro stylist tip: zip-lock bags are your friend for any liquids or items that are wet once traveling. A friend of mine showed up at the hotel on the first night of vacation, and opened her bag only to find her bottle of lotion had exploded inside the suitcase and had gotten on everything. What a mess! And what an easy way to ruin your first night of vacation. This could have been avoided by putting the lotion in a zip-lock bag to contain a potential spill. Packing cubes are great to contain dirty shoes, or dirty clothes while traveling. 2. Plan the clothes. What does your itinerary look like? Plan 10-15 simple basic pieces that mix and match to accommodate all of the fun included in your agenda. (With a few extra looks for whatever else might come up.) I will usually include 2-3 jackets in this mix - one more dressy, and one more casual. 8 tops and 5 bottoms. Wear the most bulky pieces on the flight to maximize the clothing space in your carry-on. Layering is key! With each item you add, ask yourself these two questions: does it work with 2-3 other things & can I layer it? If the answer is no, chances are it doesn't add value to your carry-on. See all of the looks I created with the pieces above, with shoppable links, HERE. Pro stylist tip: Cool weather game changers include tights or stockings (that you could layer under everything if needed), gloves, a warm hat, a stuffable windbreaker, and a blanket scarf. If you need a heavy coat, take one that compresses down. The first 4 take up minimal space but can make a huge difference in cooler weather. Wear the blanket scarf on the flight to double as a blanket when you’re cold.  3. Don’t forget a tote bag that slips over the rolling carry-on. This bag should include anything you might need to have overnight and the next day. It’s not uncommon for you to get to the gate with your rolling carry-on and tote bag only to be asked to check the rolling carry-on. Once in a while these little bags get lost and you find yourself on vacation waiting 2-3 days for your bag to show up. Yes, you may be able to track it but being able to see where it’s at almost makes the waiting-for-it-to-get-to-you game all the more painful. Pack the essentials for at least the first day in the tote just in case this worst-case scenario happens to you. How to pack warm clothes in an itty bitty bag and still have enough pieces for a variety of occasions is the classic conundrum. A strategy that includes lots of layers, wearing bulkier items on travel days, and smart footwear will have you traveling light AND prepared for the little emergencies life may throw at you. Speaking of which, you will love this post on how to be ready for any and everything while traveling here.  Looking for a little assistance with your vacation planning? I've got you. Get the details here. PACKING FOR WINTER VACATION IN A CARRY-ON WITH GOOD THINGS UTAH Comments are closed.
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Dani SlaughImage consultant and personal stylist. Dani is happily married, the mother of 3 charming children, and an Aussie named Josie Wales. Archives
May 2025
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