Today I’m making up for my absence last Wednesday and Friday (new book proposal, check), by providing you with absolutely priceless information completely free of cost. In 800 words or less (but probably somewhere around 1,000) I am going to teach you how to cram an entire week’s worth of clothes into one piece of carry-on luggage. My packing prowess is among my greatest points of pride (under showing people around Los Angeles, of course, but above writing messages in birthday cards), so it gives me great pleasure to pack it forward, as no one says. 

As you might remember, I have some general issues with suitcases as they pertain to other people, but I think that only further proves what kind of thought-time commitment has gone into this advice.

But bottom line and long story short, you’re 30 now (if I am, you are) and you shouldn’t have to waste $25 bones (or whatever those snakes at the airlines are now charging) because you can’t decide among your seventeen pair of pants.

Let’s get started. For clarity sake I’ll be fitting the following possessions into this size suitcase for a trip to NYC this coming weekend. I’m traveling for a full 10 days including a black tie wedding and week of meetings in Manhattan, so this is really putting things to the test, that I will pass. 

Dresses First – You want to be packing as many dresses as humanly possible because they provide one complete outfit in a single article. Throw on tights, which are small, and boots, which you’re going to wear on the plane ride over, and you’re done. Here are the four dresses I am packing.

• Long-sleeved hunter green shift dress
• Long-sleeved fucia shift dress
• 3/4-sleeved black-and-white sweater dress
• 3/4-sleeved leopard shirt dress  (formal-ish)
• Black tie gown (light material, easily foldable)

 These dresses will account for at least four full days in New York and one wear over the previous weekend, specifically to a rehearsal dinner. I will roll each of them and place them on one side of my suitcase first.

Shoes Second – Now that you have a color palette to work with, you should throw the shoes in because they’ll take up the most space. Whenever possible, wear the largest shoes you have on the plane. For me this means taking a red eye in a pair of knee high black boots, but they’re coming off the minute I hit the seat, and wearing them is saving me a ton of room, so I don’t care. In addition to those black boots I will pack only two other pair of shoes.

• Fancy shoes for a black tie wedding
• Black bootie shoes with a low heel

Do I want to bring 5 pair of my finest pieces of footwear? Of course. Do I want them so bad that I’m willing to lug a massive bag around? No. Also this helps me because I now have to pack an all-black round-up of clothes. Put the shoes opposite the dresses, and don’t forget to pack socks into them to save even more space!

Sweaters and Tops Next – You need pieces that can layer because they’ll take up less space than bulky sweaters. I wear cardigans over button downs and try to limit the skimpy silky tops during winter trips. Here is my list:

• A. Black tight-checked button down
• B. Black turtleneck
• C. Black long-sleeved chiffon top 
• D. Black long-fit cardigan
• E. Red cardigan
• F. Red & black checked flannel
• G. Royal blue blouse
• H. Light-knit tan sweater w/ giant fox on the front (the fox is black)
• Black camisole

Almost all of those tops can be dressed up or down for various activities. If it’s super cold I can throw the turtleneck under one of the dresses, and the cami works under the black, blue or red top. If you’re against wearing the same cami four times in one week (which is reasonable), you can either hand wash it en route or pack two because they’re tiny. Just to be a super freak about this, here is how many unique outfits you could create from the above: A+B, A+D, A+E, B+F, C+G, C+E, C+D, G+D, B+H = 10, and that’s not counting the dresses!! Gah!! I roll these too and put them to the right of the dresses.

Bottoms – Black jacks, blue jeans (2), red jeans – done. 

Every single bottom goes with every single top (except red on red, but you knew that). That is critical. I recommend on pair of jeans be “nice” and one be “knock-around” so you don’t end up with 35 outfits for meetings and nothing to wear to grab a Dunkin Donuts. These get folded or rolled and lay over the dresses and tops.

PJ‘s – Sorry but I cannot allow for plush flannel jammies in this set up. I do light grey leggings and a comfy tee. I shove these in around the open holes where the shoes are.

Socks, Undies, Tights – as needed. And no, I don’t pack half the underwear I need and wash them in process (unless I’m going for a full two weeks), I just pack mostly thongs because you’d be surprised how much less room they take up! These also get shoved into any open holes.

The In-Flight Outfit – This might be the single most important element of the entire pack. If you can get at least another whole look out of the flight wear, you’re golden. This time I’ll be wearing legitimate leggings (as in ones I would wear to dinner, not to bed), a long-sleeved denim top (that covers my butt in said leggings), a large sweater over that top (bright pink that will go with tops A. and B. above), and my boots (as mentioned).

Toiletries and Accessories – I live a travel-sized life so my make-up bag is fairly contained and can fit inside the main luggage bag along with my curling rod 😉 I keep the accessories with me in my personal item (a large purse that fits my computer) because I feel safer that way and because it’s pushing it to fit them into the main luggage too. The only remaining items are a scarf (which I wear on the plane), winter beanie (personal bag), and my evening bag for the wedding (front zipped pouch of my suitcase).

You guys, we/I did it again! Are we going to look the best we’ve ever looked? No. Does anyone is freezing cold New York care? Absolutely no! So reach out with any questions in comments and let the stress-free traveling begin!…except for the part where you have to hoist this mother load into the overhead compartment. That part’s a bitch.