Packing Essentials || How to Pack For Your Next Vacation In One Simple Carry-On

Is anyone else a complete over-packer like me? (Raising both hands up here!) I recently invested in a seriously large roller luggage piece and was still charged an overage fee of $100 because my suitcase was over the allowable weight limit.

Next question, have you ever packed your entire life away for an important vacation only to have your luggage lost by the airline? (Raising both hands here, AGAIN!) Sadly, this has happened to me not once, but TWICE. Since that time I have vowed to do my absolute best to get all my prized possessions for vacation into a small carry-on bag. An impossible task, right? How in the world could I possibly fit all the things I need into a small 21 inch bag? Never! Well, I am here to tell you today it is possible and I'll show you just a few of my strategies for doing so successfully without stress.

Shawn and I headed off to New York today (YAY! - don't forget to follow along on Instagram!) and these tips came especially handy when packing for this trip as I even downsized the size of my carry on based on the rumors in-flight carry-on requirements will soon be getting even more stringent than today. And lord knows I cannot possible have my luggage lost on a trip to the Big Apple, right?

To make it simple, I am going to break down this post down into two sections 1) with and overview of all the items I managed to pack in my carry-on and 2) my strategy and tips for fitting successfully fitting them all in with ease.

What to pack?

Clothing. When it comes to packing for vacation, I try to choose versatile pieces which I can style multiple ways and for a number of different occasions. For this particular trip to New York, I chose easy, yet stylish dresses I can dress down for an afternoon of shopping with great flat sandals or dress up with heels for dinner on the town. I also packed a number of rompers and jumpsuits for their packing ease and comfortability. You can easily throw on a great blazer or denim jacket with either for cooler temperatures.

Angela Rio Cross-Body Bag || Tory Burch Mini Robinson Cross-Body || Sole Society Embroidered Clutch || Clare Vivier Patterned Clutch (sold out) || Clare Vivier Leopard Clutch

Blue Ray-Ban Sunglasses || LOFT Sunglasses || Marilyn Monroe Sunglasses || LOFT Pink Reflective Sunglasses || Ann Taylor Sunglasses || TOMS Sunglasses

Blumoss One-Piece Swimsuit || J.Crew Panama Hat || J.Crew Leopard Sandals || Gap Distressed Denim Shorts (old) || Ann Taylor Sunglasses

Espadrille Sandals || Blanket

Accessories. I like to pack great clutches for evenings and simple, stylish cross-body bags for day. When out-and-about shopping downtown, or through a great beach market, I like my hands to free to enjoy everything around me or available to snap photos. Flat clutches in great patterns also pack well and take up little space. And no vacation is complete without a number of pairs of sunglasses and a great hat. Don't forget your swimsuit! I am loving this one-piece from Blumoss!

J.Crew Leopard Sandals || Tory Burch Wedge Sandals || Ann Taylor Ankle Strap Sandals || J.Crew Strap Sandals || Lace-Up Flats

Shoes.  I pack a combination of great heels and flat sandals. I like to be comfortable on my feet while remaining stylish. When it comes to heels, I try to choose ones that are, again, versatile and can be worn with a number of different looks. A great pair of black or nude ankle strap heels are always a win in my book! Learn later in the post about how I pack more bulky wedge sandals, etc.

Tooth Brush || Toothpaste || Q-Tips || Static Guard || Foreo Cleansing Brush || Shine Mist || Key West Aloe Save a Tan Supplies || Small Hair Brush || Nexxus Shampoo & Conditioner || Pattern LA Sunset Make-Up Pouch || Living Proof Leave In Conditioner || Revlon Eyelashes || Revlon Lip Color || Extra Hair Ties || Deoderant || Tommy Bahama Sport Sunscreen Lotion || Tommy Bahama Sunscreen Lip Balm || Amika Dry Shampoo || Whish Body Lotion || Rilastil Progression HD || Rilastil Progression HD Intensifier

Toiletries & Beauty Supplies. I'd say my toiletry bag is pretty basic like most of you gals, but there are a few things to note I simply cannot live without: dry shampoo, my Foreo cleansing brush, great leave in conditioner, bold lip colors and any of my Rilastil products! What products can you not travel without?

MacBook Air || InStyle Magazine || 'An Organized Life' Planner || Logitech iPad Mini Keyboard || iPad Mini || iPhone Case || Toshiba Portable Hard Drive

Tech Accessories. I cannot go anywhere it seems without a full on entourage of tech accessories including my MacBook Air, my iPad, iPhone, a collection of magazines, my planner and my portable hard drive to upload photos from my trip. I have also recently invested in a number of on-the-go portable chargers which are a must if you're on your phone often like me.

Packing strategy?

First.  Before packing anything, my #1 tip is to roll your clothes versus folding.  I assure you doing so will save you a ton of space and will also help lessen the likelihood your clothes will wrinkle.  Ones you've started to roll some of your pieces, makes one layer at the bottom of your suitcase making sure to use every inch of coverage possible - put small pieces like socks in small corners.

Talbots Mini Bucket Bag

Second.  If you're packing a handbag of small to medium size, set it aside and grab a large plastic zip lock bag.  Open, place the zip lock bag inside of your purse/handbag and strategically place all of your toiletry items inside.  Once filled, zip the zip lock bag for security against potential spills.  Set aside packed bag for the moment.

Third. Once you have your initial layer of packing complete, I use the empty space from my hat to fill with other items such as my swimsuits, tees, tanks, etc. to not only hold the form of the hat when packing, but to also maximize space.

Forth.  Lay the hat - one or two depending on how many you're packing (you can feel free to put another on top of the hat you stuffed) down on the initial layer from step three making sure the top of the hat is not much taller than the side of your carry-on bag.

Fifth. To secure the hat in place, pack all other items surrounding the hat, including your packed handbag filled with your toiletry items.  Again, ensure you are using every last inch available filling those empty spaces with rolled items, flat sandals, etc.  Continue doing so until your bag is completely packed.

Any smaller loose ends/items, along with your tech accessories, can be thrown into your second carry-on bag.  I love a classic tote like this one from Kate Spade as an all-purpose carry-all.  Also, I to help with not having to pack my bulkier items, I wear larger heels and jeans on the plane to avoid taking up room.

After all this, boom, you're done!  All packed and ready to go without the worry of lost baggage!

I hope these tips and suggestions have helped out!  I'd love to hear your thoughts and packing strategies as well!

Happy Wednesday!  Much love to you all!

Anna