Packing Essentials for a Summer Girls’ Trip To NYC: The 5-4-3-2-1 Rule


TME reader, Karen reached out to us on Facebook with the following dilemma: 

“In the spirit of ‘inspired by’ posts I’ve seen over the last few weeks, I thought I would submit and ask if you would consider whipping up some suggestions. A few friends and I are meeting in NYC for 4 nights (5 days) of kid-free girl bonding. We’ll be playing culinary tourists (so food baby allowance is a must) but obviously comfort and function trump everything. What basics and stand out pieces should I pack (or buy?) before heading out? Our days are likely to be spent touring (read: walking walking and more walking) while our nights will be cocktail lounges and semi-fancy dinners. My typical jeans and tees aren’t going to cut it! HELP?!”

First off, I’ll just come out and say it: I am completely jealous. How amazing does this trip sound?! A girls only getaway to NYC is the perfect way to recharge your batteries and create memories to cherish for a lifetime. And by “create memories” I don’t mean stand on a convenience store countertop at 4am and serenade the cashier with a drunken rendition of “You are My Sunshine” (because that wasn’t AT ALL what happened on my last girls’ trip to NYC) Ha..moving on…

When I read Karen’s Q, I jumped at the chance to help and maaaybe even live vicariously through her for a minute.  Here’s what I discovered: 

The 5-4-3-2-1 Packing Rule

What I originally intended to be an “essentials” vacation packing list quickly became an “everything but the kitchen sink” packing list. Oops. When I turned to the internet for some much needed help I came across something that completely blew. my. mind:

The 5-4-3-2-1 packing rule.

The originator of this idea needs some sort of award. Seriously. I am in awe of all organized, analytical, left brain thinkers because my mind just does not work that way.  To say I am unorganized is an understatement and by default, packing is no exception. My method goes a little something like this: find the biggest suitcase, stuff it with everything in sight, pray it closes. Needless to say, I NEVER have what I actually need on a trip – just every pair of shoes I’ve ever owned. 

5-4-3-2-1 is SO simple and here’s how to do it: 5 tops (one lightweight jacket or raincoat, one hoodie or sweater, at least one t-shirt, at least one tank),  4 bottoms (one pair of jeans or pants, at least one pair of shorts, at least one skirt)  3 shoes (one comfortable walking sandal, one pair of  low-sling heels for evening, one pair of sneakers or flats), 2 bags ( a daytime carry all bag and small evening bag like a cross body), then 1 dress, 1 shawl, 1 hat, 1 pair of sunglasses and 1 carry-on sized sunblock. Just for fun I added in something to read + an instant camera (it’s the over-packer in me).

If you’re only going for a few days or a long weekend just narrow the list down to 4 tops, 3 bottoms, etc.

Here’s my NYC getaway wardrobe based on 5-4-3-2-1…

nyc packing list final

Clothing Items


Denim Jacket  –  Kut from the Kloth ‘Helena’ Denim Jacket, This jacket is AMAZING, it’s been a steady piece in my wardrobe for over five years now and it’s just about the most comfortable denim jacket out (ever (2% spandex gives it the perfect amount of stretch) and it comes in five different washes. I have it in the ‘Sweet’ wash and I love that it’s a light wash that is super unique. 

SweaterFrank & Eileen Long Sleeve Sweatshirt,  I got A TON of wear out of my striped pullover on my trip, it’s lightweight cotton French terry so it’s chic and stylish. 

Tee  – Madewell Short Sleeve Harley Tee,  Gotta have a basic tee. I swear by Madewell’s tees. 

Lace CamiCAMI NYC The ‘Racer’ Top, In my suitcase, a nice lace cami is an absolute ESSENTIAL and goes just as good with a pair of skinny jeans, a clutch and heels in the Evening as it does paired with denim shorts and sneaks during the day!  

Tank – Free People’s Pretty Please Bodysuit, I LOVE the tiered/ruffle hem look but so often that means my tummy ends up being exposed. So this solves that problem! I’ve been doing it wrong all Summer!


JeansCitizens of Humanity Rocket Crop Mid Rise Skinny Jeans, I always take a pair of Citizens with me when I’m traveling. They just make me feel like a million bucks whenever I wear them and they can go from daytime to Evening easily. I love how comfortable and lightweight the fabric is, perfect while traveling. Going in cooler weather? Take a second pair of jeans, instead of the shorts. I love my white  MOTHER The Hustler Ankle Fray Jeans, perfect for dressier outings.
Dressy ShortsMadewell Paperbag Shorts,  I LOVE how flattering these Madewell paperbag shorts are!

Denim ShortsAGOLDE Dee Ultra High Rise Shorts, I am not a huge fan of denim shorts, not because I don’t love they way they look on other people, I just have had a super hard time finding a pair I like on me UNTIL THESE. They are the only pair I wear.

SkirtPaige Alamar Wrap Skirt  (for a more Summer vibe) Madewell Painted Spots Midi Slip Skirt (a Fall-Forward Print) When it gets REALLY hot out, I refuse to wear anything but a skirt, especially when I’m out walking for hours, the LAST thing I need is to deal with chaffing and sweat soaked shorts. 


Flat SandalsSorel’s Ella Sandals on sale at Amazon. These are my FAVORITE comfortable sandals of the Summer and they are on crazy sale right now on Amazon! 

Sneakers Madewell’s Sidewalk Spotted Dot Low-Top Sneakers, opt for non-white sneaks when hitting the gritty streets of NYC, I am obsessed with these feisty printed sneaks from Madewell, I ordered them as soon as I saw them!

Heeled SandalsUGG® Trina Ankle Tie Wedge Sandal, or Tom’s Poppy Sandals Both of these sandals are made for moving in and they are SO CHIC. 


BackpackRebecca Minkoff Leather Julian Backpack, if it ain’t broke don’t fix it! This is the bag I’ve taken on every single trip, vacation, night out, for over five years. So worth the money! Shopbop has a cute nylon camouflage version of the Julian that’s much more affordable and would be perfect for hot weather!

Clutch or Belt Bag – For Evenings out at the theatre and dinner, I like to transfer my essentials into a cute clutch or tote, especially after walking with a backpack all day long. My favorites right now are the    Madewell Small Lantern Bag and Rebecca Minkoff Bree Leather Belt Bag



ScarfMadewell Bold Stripe Blanket Square Scarf –  A scarf comes in handy in the city. I forgo a jacket and just bring a wrap instead during Evening activities.

Dress –  I love both of these midi options from Anthro: The  Globetrotter Tee Dress is short sleeved and has a super flattering pullover mid section (plus it’s on sale right now) and the  Bailey44 Solid Dishdasha Dress is my GO-TO for years now.My jersey tee dress is always the foundation of my vacation wardrobe. I wear it during the day if it’s super hot and in the evening with wedges. 

Hat – Madewell Mesa Packable Straw Hat is packable and perfect for a trip to the Jersey Shore or any vacation to the beach really. 

SunglassesQuay Australia Noosa 50mm Square Sunglasses , I love QUAY sunglasses! They have super stylish designs and are so affordably priced!

SPF Tinted MoisturizerIT Cosmetics’ Your Skin But Better CC+ Cream (SPF 50+), Scotti recommended this tinted CC moisturizing cream to me and I love it! It’s all you need wrapped up in one cream and I love that it’s 50 SPF!

Added Fun Stuff

Reading MaterialThe 500 Hidden Secrets of New York, I wish I had seen this book before my last trip to NYC in July. I love being a tourist, but I would have loved to check out some new spots.

Instant CameraFujifilm Instax Mini 9 Instant Camera $70 at Urban Outfitters. Because I’m a 90’s kid and I loved my polaroid camera.

How to Make Your Vacation-Friendly Outfit Stand Out

If you’re looking to spice-up your standard jeans and tee look for vacation, flowy dresses and skirts are a great way to add variation to your wardrobe. I’m a BIG believer in rocking a dress or a skirt during summer months; especially when I know I’m going to be active and outdoors. As I’ve learned over the years, my body type (hippy and thick-thighed) doesn’t take kindly to most shorts and without fail, they ALWAYS ride up/cause me some chafing or both. If you can relate, make your life 10 times easier and go for that flowy dress or skirt. Add a patterned shawl or scarf (perfect for cooler evenings, too) to make your outfit stand out even more. Here are some of my favorite pieces + other must have travel essentials:

My NYC Summer Packing List


Hope this helped, Karen! Enjoy that girls’ trip.

– Jess


  1. Love this post! The 54321 rule is really so simple yet eye opening! I have been working on a packing list for myself and two little boys for a month and a half trip to Korea over the summer: lots of walking, sight seeing, man-handling the kids, and even my grandmother’s hundredth bday (crazy!) with tons of family I have to look decent in front of… all in constant heat and humidity. Thinking of this packing rule times three. Do you have suggestions?! I’m open to any and all- Thanks for this post of wisdom!

  2. A humble suggestion – Recommend swapping out the “flat walking sandals” with cute city sneakers or even ballet flats. NYC wreaks havoc on bare feet. Seriously, your feet will be black if you’re walking around in flat sandals all day. 🙁 Love everything else on this post. 🙂

    • Agreed–great post–but as a New Yorker sandal feet are gross. Many people are wearing the adidas superstars here with everything and you would totally fit in AND be comfortable. Also, I would nix the flowy shorter skirts–unless your aim is to have a Marilyn moment over the many, many subway grates over and over again. Unless that’s your thing… No judgement.

      • Thanks you guys, advice from true New Yorkers is invaluable! It’s been more than a minute since I’ve been there so I must have romanticized it a little too much. Very much appreciated!

  3. This is a great rule for packing even if its for a short weekend. I know for me a flying/ travel bag is a must. I love my eba tote for travel because i can literally shove everything in it for the travel portion and then still use it during the trip. And the lining is waterproof so any spills is no big deal.

  4. Do not underestimate the importance of good comfortable sneakers. Very much non sneaker girl here before I moved to NYC then that was the only thing I wore. Went back for a few day solo trip last fall and walked soooooo much and only in sneakers.

  5. This post is awesome and has me dreaming of a girls weekend sans kids! In the meantime, we are getting ready to leave for Laguna Beach for a month WITH kids. I am bound and determined to NOT OVERPACK this year. I’m hoping to fit everything I need in one normal size suitcase. Do you have a post I can read to help me figure out what to bring? Help!!

  6. Do not wear new shoes. You are going to walk everywhere and those cute sandals are going to look a lot less cute with Band Aids sticking out. My friends *always* wear new shoes when they visit and they always regret it. Also, Capri pants are the new scrunchi. You are immediately spotted as a tourist. 😉

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