Tracey has a question: “We are heading down to Phoenix for two weeks and since I intend on doing some serious damage at the Outlet mall, I am hoping to pack PRACTICALLY NOTHING, so I have more room in my suitcase to bring all my new finds (and for the boys back to school clothes!) home…I am SO excited to shop at J. Crew, Ann Taylor Loft, etc, places that do not exist here in Canada!!! So ANY tips on packing extremely light (US Air charges by the bag, boo!), would be very appreciated.”

Before I answer Tracey’s question, I have a confession. Remember when I wrote about what to pack for vacation? And then I actually packed and went on vacation? Well, I took all the wrong things.

Ok, not entirely: I had two swimsuits and two coverups and plenty of running clothes and of course pajamas, which was pretty much what I wore 80% of the time we were in Florida. But the other 20% of the time, when I actually had to get dressed? Total packing fail.

I made three big mistakes: I didn’t try things on (which meant that I wound up with a skirt that is too small and a tank top that should NOT be worn in public), I didn’t take any accessories (I got overwhelmed by the goggles and Wii controllers and all the other kid things), and I didn’t think about outfits (who needs an outfit for the beach?!?).

So I wound up having a week where my swimsuit was the best looking thing I wore. Which is really and truly sad.

Fortunately, you can learn from my mistakes, and pack right for your trip. Here are five simple tips for packing as light as possible on your next outing.

1. Make an itinerary; list everything you will be doing (or possibly doing) during your vacation. Beach? Mini golf? Real golf? Dinner at a kid-friendly restaurant? Dinner at a grown-up restaurant? Write it all down. If you need to, consult with the other people vacationing with you to see what they’re planning to do. We’re going to see my parents next week and we’re having a family photo taken, so at the top of my packing list is clothing for the picture, all of which has to be carefully coordinated with my brother’s family and my parents. Once you’ve got your list, use it to assemble your outfits.

2. Try things on. This is really important. Don’t just assume that those shorts from last summer still fit — unless you’ve worn them recently, you need to test them out. And if you’re planning to mix and match pieces you don’t normally wear, for a fun vacation-y look, try those on together, too. There’s nothing worse than getting to your destination and realizing that none of your tops work with your bottoms. Go ahead and plan some outfits, too — there’s nothing worse than standing in front of an open suitcase and realizing that you didn’t bring anything to go with this particular skirt or top. Not that I did that on my vacation. No no. Not at all.

3. Assess the laundry situation. When we were at the beach, we did laundry every single day, I kid you not, if only to get the towels dry and sand-free. This meant that I could have packed half of what I did, for myself and for the kids, and still had clothes left over. If you’ll be staying in a place where you have access to laundry, or if you’ll only be away for three or four days, then pack super light. It won’t kill you to repeat pieces. If you’re not going to be able to launder anything, take that into consideration — once you sweat all over that white tee, it’s not really wearable again. At all.

4. Be honest about what you’ll wear. This is where that itinerary comes in handy. If you’re going to spend your days hiking, then a strappy sundress may not be the best choice. Touring galleries and vinyards? You might want something nicer than shorts and a t-shirt. If your week will be full of kid activities, packing for adult events is a waste of suitcase space. And yes we could have a big conversation about how vacation is supposed to be a break from the routine which means not wearing the same old clothes, but let’s face it: if you’re vacationing with the kids, you’re just taking the routine on the road. That silk sheath dress is no more appropriate for driving go karts at the beach than it is for driving through car pool at home. Sadly.

5. Take only what you need. My friend Maggie never checks a bag, and she always looks fantastic; she is a master at packing only what she’ll wear. She’s written a series of handy-dandy posts on packing light, which are really helpful. But the bottom line is this: do not put one single maybe outfit in your suitcase. If the stars will have to align in some peculiar manner for that dress to work on this vacation, then that dress needs to stay home. Period.

So what should Tracey take to Phoenix? That really depends on exactly how much shopping she’s planning to do. She could easily buy two weeks worth of clothes at the outlet mall, but if she’s shopping primarily for work, she may go home with pieces that are not suitable for this vacation. Assuming that she’s buying casual clothes, she should still pack for four full days; that’s plenty of clothes for two weeks, honestly, even before the shopping. I would suggest that she go with warm-weather basics, like shorts and skirts (two of each) with a tee or tank, or a dress or two. Dresses will take up less precious space in her bag, but they’re only worth taking if she’ll really wear them.

And of course, she should pack an extra bag, in case she really scores at the outlets. It would be a shame to buy a whole new wardrobe and have no way to get it home. (Although she should also look into shipping things — I doubt that it will be cheaper than checking a bag, but it’s worth researching.)

What’s your best packing light tip? Let’s hear them, because clearly I need some help.