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7 Universal Tips for Selecting Your Winter Travel Wardrobe

Packing a week’s worth of clothing in a carry-on is fairly easy in Summer, but in Winter—when you have bulky sweaters, hefty shoes, and multiple layers of clothing, it can be a bit tricky. After I spent an afternoon planning ahead, I managed to get it all in one carry-on with room to spare for other essentials. 

A friend who wanted my packing help said to me, "I love your outfits, but I don't think I can do what you do because not only is your style is different than mine, but also your size."

So I'm aspiring to share 7 universal tips for packing in Winter. These tips are cumulative, so I've labeled them in Steps--
and if you want to see my personal 7 day wardrobe, click here.

Step 1: Check the weather. My 7 days in Rome forecasted 5 days of cold rain.

Step 2: Plan your shoes. Most of the time when you travel, you spend more time on your feet than on ordinary days, plus you don't have access to your entire closet of shoes. You need GOOD SHOES--supportive, comfortable, weather-appropriate, and versatile. When packing for Summer, I work the outfits around a color pallet, in Winter, I work it around the shoes.

I knew for a week of rain that I would regret not having rubber rain boots (because in Italy the main mode of transportation is by foot!) Even though mine are hot pink, they were the first item selected—all else then revolved around this. However, they are not my most comfortable shoe, so I knew for those really long days of excursions, I would want my black boots by Hushpuppies (this was a trusted brand when I was a kid! They still don’t disappoint!) I added a Doctor Scholl’s arch support to them as well. I can seriously walk in them all day and my feet don’t hurt (they are tired, but not hurt).

Then I packed a comfy pair of canvas flats, just in case I wanted a break from boots in and around the hotel. I was glad I did this.

Step 3: Choose pants that work with your shoes and weather. I needed pants that would tuck into my boots (boot cut/bell bottoms walking on slushy streets = bad idea.) I chose warm, fleece-lined brown and black leggings and my most comfortable pair of skinny jeans, which happen to be navy. Immediately I thought, "Can I bring 3 different neutral colors and still keep my packing to a minimum?" Yes!

Step 4: Select versatile coordinating layers.  Limit to 3 outer layers.

This is where I spent the majority of my time planning. You can't fit 7 days worth of double layers in a carry-on unless you repeat the layers. Everything must coordinate and hold the potential of being worn multiple days. If you think this is not clean, keep reading.

I chose 3 under layers, 2 versatile layers, and three outer layers. Italians do not have extensive wardrobes. Yes, Italy is fashion central, but people invest in quality, not quantity. It is the norm here to see people wearing the same things repeatedly in a variety of ways. Also laundry in Italy is a lengthy and expensive process. Washing machines are small, dryers are rare. In the winter, it can take a few days to complete a wash and dry cycle, therefore, people wear things multiple times before laundering. You can too, especially in Winter when you're not sweating as much. ;)

But I still planned my layers for optimal cleanliness. Each under layer worn only once or twice. Each versatile layer(in this picture, the ones with collars are my "versatile layers") can be worn as an under or an outer. I wore each collared shirt as an outer layer first, and saved it for an under layer toward the end of the week.

I limited to THREE BULKY ITEMS ONLY. 2 versatile sweaters, and one fleece. I knew that at minimum, I would want the fleece when it was time to get comfy in the hotel or at the continental breakfast before going out for the day, but I wanted to incorporate it into an outfit as well.

After choosing the layers, I realized that they would not all suffice to cover the leggings by themselves. See flow chart “Are youwearing pants?” ;)

I chose one cream mini-skirt, and 1 pair of black skorts to wear over the leggings. These + leggings take up the same space as a regular pair of jeans/pants if you opt to go that route instead.

Step 5: When choosing Winter accessories, skip necklaces and bracelets, and instead opt for scarves and earrings. Statement necklace snag sweaters, take up weight and bulk, and are covered by your outerwear half the time anyway. Scarves are a two-for-one as they add style to your outfit, but keep you warm. I chose one heavy knit scarf, a casual blue, and a two-way white/gray scarf with a sheen. All 3 scarves coordinated with all three pair of shoes.
I limited jewelry to fun earrings, and only my favorite, small, meaningful bracelets. Clunky bracelets are lost under coats, and are in the way when shifting layers on and off, which happens frequently. I heard fashion advice a few years ago: have only one piece of statement jewelry. Since I was forgoing bracelets and necklaces, earrings are big and fun and stand on their own!

I included a hat to add variety to an outfit or hairstyle while also providing warmth, and I made sure to pack a hairband and rubber bands for potential bad hair days. 

Don’t forget that lipstick is a great accessory which draws focus away from messy hair!

Step 6: Cross-body bags, 1 big, 1 small. This is not just for style--cross-body bags free up your hands and also prevent theft. Because of my weather information in Step 1, I brought a small water-resistant cross-body, and a mid-size bag for carrying my computer and notebooks (my trip was for business/study), but when I travel for tourism/shopping, I opt for a larger tote-size. My small cross-body has removable straps so it can double as a clutch for a fancier night out.

Step 7: Ignore temptation to add more things! Stick to the minimum! At this point, I thought there was still plenty of space in my carry-on to add a few extras--"Aww, maybe one more sweater and scarf..." but no, there was still Pajamas, toiletries, my computer, my Bible, and other unmentionables, etc. Note that I do not re-wear socks or underwear.


I brought enough for new daily wear, and tucked them in my shoes for packing, which allowed space for all the other necessities plus my special favorite pillow and a roll of TP! (I don't like hotel sandpaper TP so I always bring my own!) :)

That's it! 7 Universal tips wardrobe tips for a week in Winter!

I easily fit all of this in a carry-on, and if you'd like tips for packing efficiently, just search youtube carry-on packing for some helpful tutorials.



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