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The countdown is on. If you are heading out of town for the holidays, this is the time when packing anxiety hits you full force. Is it too dressy? Will I be comfortable? What about the weather? As a personal stylist for women, I talk a lot about individual style and body types. Yes, there are essentials, capsule collections, uniforms, call them what you like but many women are looking for a straightforward list of what to own and what to skip. Or, in this case, what do I pack and what do I leave at home.
Let me begin by saying that every woman's list will be different. But, this is a nice place to begin. Start with the essentials and make revisions as needed. After all, this is all about you. Safe travels!
The Stylish Woman's Holiday Packing List
1. Dress or Jumpsuit.
It doesn't matter where you are going, you could end up needing something nice to wear. Bringing the right dress or jumpsuit is key. You want something that can be dressed up or down. It's not too fancy, but it's not too casual. Also, it should be comfortable. In fact, it should be so comfortable that you can also wear it on the flight.
When to wear: On the plane, at a dressier event like the holiday dinner, as a casual everyday outfit.
Let's be real. The majority of Americans think of a great pair of jeans as the comfort food of their closet. Make sure you bring a pair on your trip. Ideally, these can be worn with a standard length top or with a tunic. Skinnies or straight leg are usually the way to go, in this case. Remember the cuts that work for your body type and stick to those. If you are going somewhere where distressed denim is appropriate, go for it. If this is a classier trip and/or you'll see family that won't love the distressed look, a dark pair is great, too. Really, you want something versatile.
When to wear: On the plane, as a casual everyday outfit, with the tunic or top.
3. Tunic/ Long Top.
This is the money maker. Bring along a dress that can also be worn as a top. This approach won't work for every body type, but if it works for you, it's going to make your trip easier as you can wear it solo or with your culottes or jeans. If it's warm outside, you can skip your tights and wear it with your slip on shoes. If it's cold, wear your boots and tights. An a-line dress will usually give you the cut you need to work over a pair of pants. Look for something that will not press against the button of your jeans so that it shows through. Knit often works well. Long sleeve means you can skip the cardigan if it's cold. Short sleeve or sleeveless work with layering.
When to wear: As a casual everyday, for a slightly dressier occasion.
4. Long Cardigan or Kimono.
This cozy piece works over everything on this list. If you are cold, you'll need it. If you feel like you need a top layer to complete your look, you'll need it. If you want a pillow for you or your loved one on the plane, you'll need it. If a kimono is more your speed, you'll get lots of use out of that, as well. Kimonos work for layering, just like a cardigan. A kimono is also ideal for loungewear or you can belt it and wear it as a dress.
Whether you go with a cardigan or kimono, opt for a color that works with everything on this list. In fact, when you lay out these items, everything should be able to mix and match. It may sound crazy, but after years of working with all types of women, I find that most have colors that work well together in their closet. Don't be afraid to mix and match unexpectedly.
When to wear: As a casual everyday, on the flight, for a dressier occasion as long as it's styled up, as loungewear.
5. Boots that Work with Jeans or a Dress.
Let's think about where you are going. You need the proper shoes. Your feet need to be warm and so do your legs. If you are going somewhere especially cold, stick with knee high or over the knee boots and some cozy fleece tights. If the temperature is more reasonable, an ankle or mid calf boot works just fine. You simply want that boot to work with jeans, the dress and/or the tunic. Boots are a place where you can truly express your personal style. Think moto versus cowboy versus docs versus fashion forward. Do you, my dear.
When to wear: When you want to look cool and stay warm. On the flight is an option if you need room in your suitcase.
6. Slip on Shoes.
If there's any chance that you'll be spending lots of time in a shoe-less house, you'll be very happy about having slip on shoes. When you head through security at the airport or are the passenger on a long car ride, you'll be happy you have slip on shoes. Try something that is flat and comfortable so it's also casual but chic enough to be worn with your outfits when skipping the boots. Or, if you like a heel, just make sure it's one that is super functional for your trip. Again, express your personal style through your feet. Opt for convertible mules (shoes that are open in the back or can be worn as traditional shoes), pointy toe flats, loafers, clogs, etc.. A slip on sneaker can work if your style is especially casual or you have a sporty vibe. You might consider an animal print, patent leather nude, metallic or other fun but still super versatile flat that can be worn with any of the pants, dresses, jumpsuits or tunics on this list.
When to wear: On the flight, in the house, in the car, out in the world.
7. Jersey or Silk Culottes or Joggers.
These are essential and are a common piece that get left behind. Here's the thing: these pants can be styled up for a dressy occasion, worn as a casual everyday with a tunic or top OR as loungewear. That's right, folks. If you are staying with friends or family, it's vital that you think about what you are wearing when you are transitioning from day to night. If you've been out in the snow and want to put something comfortable on, it needs to also be something that you can wear in front of friends, family and kids. That, most folks remember. But, loungewear can also still be elevated and express your personal style. That's the part that gets forgotten. A super comfortable and hip pair of joggers or culottes can do just that. Stick with black if you are flustered.
When to wear: At a dressy occasion with an elevated top or tunic, as a casual everyday, as loungewear, during your travels.
8. Long Sleeve Top.
This one is all about your personal style. If you are looking to be more casual, go for a long sleeve Breton tee or another comfortable option that works well with your culottes, jeans or joggers. A classic white, chambray or oxford button up is a win, too. Alternatively, try a long sleeve blouse that is still functional for your activities but is dressy enough for any situation. Wear this top with any of the bottoms on this list. and your boots or flats. In some cases, you can toss this over your dress and transform that into a skirt.
When to wear: Depends on how dressy you go, but this can be for a nice dinner if it's a blouse. Otherwise, it will work for casual everyday, the flight and if it's a tee, loungewear.
9. Bathing Suit.
I can hear you writing this one off as you are headed to a cold location. Don't. Worse case scenario you end up with an opportunity to go to a hot springs in the snow or a hot tub. These situations tend to sneak up on us and having to decide to skip the party or go sans clothing isn't ideal. Always pack a swimsuit.
When to wear: Oh, you'll know.
I say this all the time, but your coat is everything. If you can only afford one great piece, it should be your coat. It makes the first impression in so many situations. Did you see that scene in, "Home for the Holidays," when she runs into someone from high school and she's wearing an awful coat? It haunts her. When traveling, wear your stylish wool coat. If it's going to be super cold where you are headed, you can layer a down parka underneath, if need be. Or if you have a super stylish down parka, sure, wear that. If you are going somewhere warm, bring a lightweight trench to finish off your outfit.
When to wear: Whenever you need another layer to keep you comfortable, when you want to elevate your look for the grand entrance at an event.
It's so tempting to skip accessories on trips. After all, we're all just looking to take a break from it all. But packing a few pieces of jewelry elevates every look and is a gift when you decide to skip your makeup or hair routine and go for something less labor intensive. Just bring earrings and a bracelet or a necklace and a ring, as an example. Or bring a collection. Opt for pieces that go with everything you've packed. Sticking with metallics, wood or black pieces (if you are bringing black shoes) makes things super easy. You can always add on pieces that have more flavor to keep things interesting. Over the years, I've noticed that the girls in my family have really enjoyed digging through my accessories and wearing them (when appropriate) on the trip. It's fun for them and fun for me. Accessories go beyond jewelry. If you wear scarves, be sure to pack at least one to elevate your looks and keep you warm. Choosing the proper handbag for travel is a big decision. Try to go for something that can be hands free- a cross body, leather backpack, over the shoulder bag as you never know your situation. Straps also give you a place for your sweater if you get too hot during your outing. Just slide it between the strap and your body and tie so it won't fall to the ground unexpectedly.
When to wear: Everyday except with your loungewear. (FYI- You CAN wear them with your loungewear, but it isn't necessary.)
Last but not least, notice that I didn't mention leggings, my Dear Reader. That's intentional. You can do better. Yes, leather or vegan leather leggings will work. But those are the exception. I have confidence in you. Look and feel beautiful and enjoy your holiday.