After "Travel Light - Two Weeks In A Carry-On," the number one question I received was "this looks great for summer, but how do I do this for winter?"
It can be done, I promise!
I'll briefly touch on some of the original tips here, but if you've been here a while, you can skip through below to see the outfits.
The bulk of the work in traveling light is planning. Preparation is everything. You must spend a couple of hours thinking through this, and not wait until the night before. I can't stress this enough. Take your time. Think it out. You'll also breathe easier not running around the night before haphazardly packing. This leads to forgotten items and overpacking.
Ready? Click through the jump to see the tips + outfits to take.
WHAT'S IN MY SUITCASE
Charter Club Grey Cashmere V-Neck Sweater | Charter Club Black Cashmere V-Neck Sweater | VS Feather Grey Heather Tunic Sweater | Bar III Black & White Drape Cardigan (Similar) | Bar III Oatmeal Cardigan | Alfani Burgundy Blazer (Similar) | Madewell Chambray Button-Down | VS Hunter Green T-Shirt | J.Crew Grey & White Striped Tee (Similar) | Black Leather Pencil Skirt | Merona Grey Stripe Dress (Similar) | Mossimo Burgundy Pencil Skirt | Style & Co Black Skinny Jeans | Kenneth Cole Reaction Black Ankle Boots (NO LONGER AVAILABLE - SIMILAR) | Kenneth Cole Reaction Taupe Ankle Boots (NO LONGER AVAILABLE - SIMILAR) | RH Brown Leather Riding Boots (Similar) | Mossimo Infinity Scarf | Fossil Watch | Merona Brown Skinny Belt | Dorothy Perkins Black Skinny Belt (Similar) | Banana Republic Necklace (Similar) | Gap Parka (Similar)
Bags: Samsonite Suitcase | Nest Shoulder Bag | J.Crew Crossbody Purse | Eagle Creek Black Packing Cube
TIPS FOR TRAVELING LIGHT
What will you be doing on your trip? Exploring a city? Spending time with family? Heading to the office? Maybe you have a holiday party to go to. For this particular trip, I am going to the office for a week, and spending time with my family for a week, with some dressier holiday functions in between.
Choose Dual Purpose Items + Learn To Love Layers
Try to make sure each item you take can be worn with more than one outfit. This is the only way you can pack for 14 days. Each item should have at least two uses, if not three or four.
The easiest way to stay warm when traveling during colder seasons is to layer. Three thinner layers are always warmer than one bulky layer. I can promise you this, from experience walking around 30 degree weather in New York City in the snow. For trips this time of year, I love cashmere sweaters layered with chambray button-downs and for really cold trips, a long sleeve tee underneath that's whisper thin and traps in your body heat.
Try to wear the bulky items on the plane as long as you can remain comfortable doing so. In the fall and winter, this means wearing your jacket onto the plane. You can stuff it in the overhead or under your seat once you're on the plane. Or if you're like me, it can double as a blanket when you inevitably get cold mid-flight.
Spend Time Selecting Your Outfits + Snap Some Photos
Include your shoes & jewelry. Pick a few accessories that work with everything. For me, this includes my watch, two statement necklaces, and a pair of studs. Pick one or two belts that make an impact to jazz up a plain dress or to wear at your waist over a cardigan.
Take at least one nice dress. You can wear it out for a nice dinner or with flats for a casual look.
Choose your shoes judiciously. You don't need a pair for every day. I generally wear riding boots on the plane and pack a pair of ballet flats and ankle boots. And if it's really cold where you're going, I'll show you how to fit the wellies in, too.
Once you've selected your items, lay them all out. I like to take photos of each outfit with my phone. That way, when I'm traveling I can reference the photos. This also serves as a way for me to check that I have enough items and looks without making a list.
Learn To Fold Like A Pro and Maximize All Spaces
Stuff every empty space in your suitcase to take advantage of nooks and crannies that might otherwise sit empty. I stuff everything - tights, belts, necklaces, even pajamas - in boots.
Do you think you can pack for two weeks in a carry-on? Where are you heading this winter?
I'm always happy to answer any questions in the comments!
The easiest way to stay warm when traveling during colder seasons is to layer. Three thinner layers are always warmer than one bulky layer. I can promise you this, from experience walking around 30 degree weather in New York City in the snow. For trips this time of year, I love cashmere sweaters layered with chambray button-downs and for really cold trips, a long sleeve tee underneath that's whisper thin and traps in your body heat.
Try to wear the bulky items on the plane as long as you can remain comfortable doing so. In the fall and winter, this means wearing your jacket onto the plane. You can stuff it in the overhead or under your seat once you're on the plane. Or if you're like me, it can double as a blanket when you inevitably get cold mid-flight.
Spend Time Selecting Your Outfits + Snap Some Photos
Include your shoes & jewelry. Pick a few accessories that work with everything. For me, this includes my watch, two statement necklaces, and a pair of studs. Pick one or two belts that make an impact to jazz up a plain dress or to wear at your waist over a cardigan.
Take at least one nice dress. You can wear it out for a nice dinner or with flats for a casual look.
Choose your shoes judiciously. You don't need a pair for every day. I generally wear riding boots on the plane and pack a pair of ballet flats and ankle boots. And if it's really cold where you're going, I'll show you how to fit the wellies in, too.
Once you've selected your items, lay them all out. I like to take photos of each outfit with my phone. That way, when I'm traveling I can reference the photos. This also serves as a way for me to check that I have enough items and looks without making a list.
Use A Hard Sided Suitcase + Push The Limit Of Your "Personal" Item
I realize it seems counter-intuitive to use a suitcase that limits the amount you can carry, but trust me on this one. A hard sided suitcase helps compress the items and keep them from wrinkling. I chose a lightweight, spinner wheel model to zip through the airport and make it easy to lift above my head into the bin. Even when it's packed solid, I can maneuver this suitcase with ease. To keep it organized on the inside I use this large packing cube for clothes. This turns a cavernous space into neatly organized compartments for all my essentials.
In addition to the carry-on, utilize space in your personal item. Think outside the box when you're selecting a bag to find options that are stylish but spacious. Mine is actually a designer diaper bag (stay with me) by Nest made from genuine leather with classic gold hardware. It has tons of pockets to keep things organized, it's built to withstand a lot of wear and tear, and since it's big enough for my MacBook Pro, I use it as a work bag after I arrive at my destination.
This bag is large enough to hold an extra pair of shoes, my scarf, a crossbody purse, my curling iron, hair brush, noise canceling headphones, MacBook Pro, glasses, snacks, iPad, and medicine. Make sure to toss your toiletries in containers 3 ounces or less (I love these for beauty products and these for shampoo & conditioner) and place them in a clear plastic bag to remove at security.
I cannot emphasize the importance of learning how to fold clothes properly. For me, this is a skill I honed while working at Gap during high school. For the rest of you, I suggest tutorials by Martha (who else?) How to fold a tee, a button down, and jeans or pants. Keeping your stacks of uniform size and shape prevents wrinkles and takes up less space in your suitcase.
Stuff every empty space in your suitcase to take advantage of nooks and crannies that might otherwise sit empty. I stuff everything - tights, belts, necklaces, even pajamas - in boots.
Do you think you can pack for two weeks in a carry-on? Where are you heading this winter?
I'm always happy to answer any questions in the comments!
