I know what you’re saying, I totally get it: you’re packing for a trip where you’ll be meeting exciting people and doing exciting things, taking lots of photos and walking a ton. You don’t want to be weighed down by multiple bags, but you have MOODS, you need a multitude of spontaneous options to suit them! But what’s worse…? Not getting to wear your over-the-knee-boots when you are in a distinct over-the-knee boot mood? Or lugging a steamer trunk of clothing up and down crowded subway stairs and/or having to take a $100 worth of cab rides to and from the airport?
What to do!?
I recently packed for a ten day, 2 leg trip to New York and Chicago with a fashion show and cocktail party, a business meeting, a broadway play, a wedding and plenty of urban hiking in the cards. I was flying the dreaded American Airlines (who charge extra for a checked bag) and planning on taking as much public transit as possible, so I decided all this fun needed to fit in my carry-on sized convertible backpack. It took me a few hours and a masters degree in Tetris to pack, but it was sooo worth it! I felt chic, put together and comfortable all week and didn’t even have to resort to vacation laundry!
What’s that you say? Oh yes: SKILLS.
I’m officially qualified to write this post. Says me.
Tips and Tricks for Bringing what must be Brought:
Pick out your favorite things.
Do it up, you’re on vacation! There will be more pictures of you during these upcoming days than you’ve taken in the past month so wear things you’ve been saving for those nonexistent “occasions” – this is it. Choose a maximum of one thing per day that tickles your fancypants most and lay em all out on your bed. Then pick out your best neutral, time-tested staples and see how many fancy-ticklers you can pair with the each one. Pack only the staples that will go with more than one of your chosen pieces. And try to make sure that each piece is different- no need to bring your black skinny jeans AND your black cigarette pants. Bring the ones you wear most and leave the other home, believe me, they’ll miss you more than you miss them.
Wear wool.
Ah, the technology of nature. Wool is comfortable, repels stink and sweat, keeps you cool in summer and warm in winter and nowadays, is the antitheses of “scratchy.” Invest immediately in an obscenely soft wool undershirt and you will come home with a suitcase full of freshness. You can even wash your “baselayer” wool in the hotel sink.
Economy of Duds and the Power of Accessories.
Plan for the unexpected and stretch out what you’ve packed with a little finesse.
Maybe your hotel doesn’t have a pool, but what could it hurt to bring an eensy little swimsuit in case you meet some hip kids who propose a late night dip? Consider bringing a one-piece instead of a bikini in case you want to wear it as a bodysuit with your high-waisted jeans. Eh?! Look at you, always thinking ahead! Accessories too! They’re teeny. Maybe you don’t need that rhinestone hairclip… but what if you decide to crash a cocktail party and have the need to whisk your sundress away from the day and into the night??
Conversely, if you have multiple semi-formal events, see if you can’t make a formal outfit from separates that you can wear again, uh, separately, dressed down for brunch or a walk on the beach.
Check the forecast.
Duh! The weather can change as often as you do, so I recommend lots of layering options. You can wear layers multiple times and no one will notice. Bring a leather jacket – it’ll break the wind, keep you warm, save all the suitcase room your down parka would hoard and can double as a light jacket for an innocuous spring breeze. Things like knit hats, leggings, wool undershirts and scarves are invaluable in an unexpected cold patch (or bad hair day) and hardly take up any space at all. If the weather looks like it’ll let you get away with nothing but sundresses and rompers, right on, because dresses are space-savers, but if you’re anything like me, you might wanna mix it up with some shorts and skirts to avoid that feeling of wearing a uniform.
To pack light, pack tight.
It defies all reason, but I swear that rolling your clothing before shoving them into your case actually does reduce their cargo space. Fold everything carefully in half longways and flatten them out before rolling them up and wrinkles should be scarce. Shove socks and underwear into shoe cavities and hats. Pack a cloth bag to wrap your shoes, hold your dirties or bring home extra shopping in.
Shoes are bulky
If you really must bring those clunky platform brogues, plan on wearing them to the airport and on the plane to save space. Low profile flats are space savers and good to have in your purse when those sandals you THOUGHT were comfortable start eating away at your ankles. Make sure the heels you bring are versatile enough to wear with jeans or a cocktail dress.
Most importantly, HAVE FUN!
I’m now going to apologize now for my slothful posting schedule lately and list my excuses with bullet points. Get this:
-I’m planning 2 parties – my bf’s birthday and sister’s baby shower.
-I’m organizing, styling and art directing a big 60s circus-inspired photoshoot with 3 stunning blondes and some handmade indie designer duds.
-Eve and I are posing for an amazing fine art photographer and his camera from the 1800s.
-Still playing work catchup from our New York/Chicago vacation.
-I have Jury Duty next week.
-All this needs to get done before I start packing for our Painfully Hip ROADTRIP in 2 wEEKs!
I hope you can you forgive me.






















We pay someone to come to our library(ies) and tell us all about how to pack smart for a trip. The program is hugely popular and we get anywhere from 80 to 100 at my branch alone. I’d much rather pay you for that program. I’d love to draw in the non-geriatric crowd and I think you’re just the Holly Golightly to do it! In fact, I can think of lots of Painfully Hip centered library programs…(an alternative fashion show, perhaps?)
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I, too, am a roller.
Your “special occasion” trick is a good one!
SBJ’s last blog post..Sea-femme by the seashore.
Yes packing can be a bitch.
The last time I went travelling I was packing for an Eastern European spring/summer climate, followed by an extremely hot Moroccan summer.
Problem is, dressing up in Eastern Europe is NOT the same as dressing up in Morocco. Especially the tiny town I was in.
One tip though. Mackage has an amazing rain jacket that zips into a cute little purse. These have got to be the hottest rain jackets I’ve ever seen.
Gabrielle’s last blog post..I Think I Creamed Myself – Google Squared Released
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[...] boot mood? Or lugging a steamer trunk of clothing up and down crowded subway stairs an click for more var gaJsHost = ((“https:” == document.location.protocol) ? “https://ssl.” : [...]
You got SKILLS indeed! Rolling small items inside shoes help, too.
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Hey — this was great advice! I *hate* packing for a trip and end up wearing 2 outfits over and over again. I envy the bf because he just throws 2 pairs of jeans, 8 black shirts and a sweater into a duffel and wonders why I can’t figure out what to put in my suitcase. This was really helpful. AND – you looked great at the wedding!
Katherine’s last blog post..Friday Garage Sale Open Thread
Great Post… now if i just had somewhere to go
This post was amazing! You guys are completely genius.
A very useful post. I find if I have time to plan a bit when packing I end up packing much lighter and have a more suitable selection when I get there. If I am in rush I just chuck everything in but the one thing that I really need.
Wow sounds like you are really busy, enjoy your trip, you have inspired me to go on a trip around the UK (when I have time)
Posh Swaps’s last blog post..The 3 R’s Reduce, Reuse and Recycle for Clothes
You are forgiven, and this post was awesome. I do have some packing skills as well, if I do say so myself.
I also like to just bring a backpack – soooo much easier!
Eyeliah´s last blog ..The World is Love and Life are Deep
This has been super helpful, next weekend I am going away and I always have a tenancy to pack everything that is in my wardrobe!
Jessica´s last blog ..Etsy finds of the week – Reworked antiques
on a side note, whoever took this photographs is just awesome!
[...] my clothes are my favorites. (do you have any idea how hard that makes it to pack? i swear by the rolling method. i wouldn’t lead you astray on this one. i think i got 27 days worth of outfits into one [...]
Uh, I’m allergic to wool.
sob sob.
[...] asking politely if she could guest host on The Bonnie Hunt Show. I thought I had the subject of packing light covered, but now she’s gone ahead and one-upped me like I’m, well, Bonnie Hunt. Thanks [...]
nice blog..anyone who likes beach weddingdresses ?
Doc´s last blog ..Wedding Dresses Discount