How to Travel Light

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I basically live out of a suitcase.
Rarely do I book a round trip flight. I am always booking a one-way... meaning I don't always know where I am going next or how long I will be gone. 
Frequently, I am asked the same question: How do I pack when I never know when I will be returning? 
The answer is simple: TRAVEL WITH JUST A CARRY ON. 
This will make your life so much easier... in all circumstances. Here's why:
1. You don't have to waste time (especially if you're in a hurry to catch a flight) checking your bags.
Forget about having to show up to the airport super early. If you can manage to travel with just a carry on, you don't have to waste time and money checking your bags at the airport. Simply have your mobile boarding pass ready and head straight to TSA. 
2. You have your luggage with you at all times. 
You don't have to worry about your luggage being thrown around or getting dirty/damaged. 
3. You don't have to worry about your luggage getting lost/misplaced. This happened to me when traveling to Rome last November. I wore the same outfit and makeup for three days. Needless to say... I always bring the essentials WITH me on a carry on ever since. 
4. SAVE TIME & MONEY 
Again refer to number 1. 
I don't know about you, but the first thing I want to do when the plane lands is immediately hop off and get out of the airport as fast as possible to get to where I'm going. Side note: DON'T be that person that gets up immediately when the plane lands and tries to push to the front. Just don't. Anyway, when traveling with just a carry on, you can save the hassle of figuring out which carousel your bag is located just to wait another 20-30 minutes to arrive. Or save yourself from the panic of arriving to your dream vacation only to be the only one still standing at the bag carousel to realize that your bag, along with all of the fashionable outfits you planned to take photos in, are lost. 

Now the question is...
How do I pack for weeks at a time and fit it all into a little carry on?
Don't underestimate yourself! You will be shocked at the amount of stuff you can fit into a 22 x 14 x 9.

​The first step to packing light is to wear you heaviest or bulkiest items. 
In the photo above, I have on my thickest sweater, jeans, and shoes. This seriously saves SO much room in my bag! When going on a trip, I normally bring a max 2-3 pairs of jeans, and the same with shoes. Flip Flops you can always zip up in the small side pocket of a carry on, or stick them in your purse if you are bringing one. This is the sole reason I wear heels to the airport. Hence the name, Wander in Heels. Tie a jacket you are bringing around your waist to save even more space. 
If you are bringing a coat, wear it. Sometimes I bring a coat and a cute heavier jacket. So I either wear or carry the jacket on my arm, and wear the heavy coat. Choose only one hat to bring, and wear it. If you want to bring another, let it sit on top of your purse instead of cramming it in your bag.

The other secret to traveling light is to have a big purse. I LOVE my Christian Louboutin Cabata Leather Tote. I linked all available here: http://liketk.it/2vg5y 
I have been traveling with this bag for over a year now, that's how much I like it. Not only do I get compliments on it everywhere, but it is the sturdiest, roomiest bag for all of my things. I have thrown it around on countless flights, ubers, trains, and taxis and it is without a scratch. 
I stuff this thing full. The things I normally put in my purse to slide under the seat in front of me on an airplane instead of my overhead carry on include: Laptop, large headphones, planner, makeup bag, curling iron/straightener, liquids in a quart size freezer bag, snacks, sometimes a pair of heels, etc. Crazy, right? Its do-able. I manage every. single. time. :) 

I also wear a cross body bag. You can wear it underneath your coat when boarding the plane so that it doesn't count as a third bag. I put my ID, passport, credit card, chapstick, etc. in my cross body so that I don't have to worry about losing important items or digging in my purse to find them.     
​                                                         Here are some of my favorites:

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Packing for weeks at time to fit in a carry on size bag is not only a sport, but a fine art. 
This last trip had to be the hardest to pack for. Transitioning between warm weather and cold. From summer to fall. I went from NYC to Florida, Florida to NYC, and NYC to Boston. I was traveling for playoff baseball... so who knows? I could have been in NYC and around until the end of October! I had to be prepared for anything. 
Now prepare to be amazed. 
Here's what I fit into my RISE gear carry on bag. 
     Zipper pouch on top of riser: accessories, jewelry, misc items.
     Top two pouches: Three swimsuits, three bras, countless pairs of socks/underwear.
     1st shelf: baseball jersey, suede jacket, two body suits, three casual dresses, two sweaters,
     six tops. 
     2nd shelf: two pairs of jeans, one jumpsuit, two rompers, five dresses. 
    Bottom (laundry spot): two pairs of workout pants, three pairs of workout shorts, four 
   workout tanks, one pair of tennis shoes (Adidas are flexible), two pairs of heels. 
     Side pockets: one pair of flip flops, one long jacket. 

The best thing about this particular carry on bag is that you can just hang up the riser once you get to your hotel and be completely organized your entire trip. No more overflowing bag with wrinkly clothes all over the room. Keep everything neat and most importantly, stress free! This bag has been a total lifesaver for me.
Here is the link to purchase: RISE Gear Roller Grey 
If you already have a carry on roller bag that you like, simply purchase the insert here
If the Rise Gear Roller is sold out (it is often), Here are a couple TSA approved carry-on size four wheel roller bags that you can use the insert with:

I hope this helps you in all of your travels! Please comment below your thoughts & questions. :) ​