When my mother moved back to her native Michigan four years ago, I started a new tradition of bringing my family to visit her once a year. We choose fall to visit because it’s so beautiful with the changing colors, and it’s my favorite season. I think next year we’ll visit during summer so we can swim and enjoy the long, warm evenings. In this photo, we’re all sitting on a built-in bench couch in The Palmer House, a Frank Lloyd Wright built home in Ann Arbor. You can rent this house and experience FLW’s magnificent Usonian design yourself!

These days, I like to travel light, but I also like to tell a story of who I am, especially when I only see my family once a year. I want them to know how I’ve evolved, what my new passions are, and how I express myself these days.

I don’t always get it right, but this year I got it mostly right — except for the fact that Michigan had unseasonably warm weather so I didn’t get to wear my cashmere sweaters.

After traveling to Michigan last week, here’s five things I’ve learned about packing that might help you on your journey of self-expression, too:

1. Pre-tested always wins.

We each have pieces in our closet that are repeat favorites. You know, those things that bring compliments, no matter how many times you wear them. For me, it’s a Fleurette cashmere coat that can go over a pair of jeans and a tee shirt or a fancy dress. When the weather gets chilly, I always carry this coat with me. I look and feel put-together in this coat, and that gives me reassurance that I will look good walking into any place!

2. If it’s a foundation piece, it needs to be perfect.

Your foundation pieces, like tee shirts, white blouse, and even jeans, need to fit like a glove, have character (your best color, neckline), and be of lasting construction and fabric. They don’t need to be expensive, they just can’t look cheap or worn out. It’s all about bringing basics, like a great cropped jean (which I wore 2 or 3 times on this trip), a sleek turtleneck, a great cardigan, a classic trench coat, or a pair of comfortable loafers. Your basics should look substantial, expensive, well-made — that’s what makes an outfit easy to put together.

3. Several pieces of good jewelry can make your outfit.

Every woman needs a few well-loved, get-noticed pieces that have the power to bring even the simplest outfit to life. I brought a slew of my favorite “Helen Anderson Creations” necklaces, and stacked them around my neck to make a simple tee shirt and cropped jeans outfit look stylish and interesting. I had so many pieces that my daughters were borrowing them to add pizzazz to their outfits, too! If your jewelry is a keepsake, never pack it in checked luggage — carry it with you. Check out my jewelry designer friend’s selections she’s selling on my website, Haute Necklaces by Helen

4. Plan your outfits like a pro.

I teach this method in my virtual Style Workshop because it will make or break your trip. Having the confidence that you are bringing everything you need, and nothing you don’t need, will dramatically scale back the stress factor.  Here’s what  I do: make a list of every day you will be gone, what you anticipate doing each day and evening, and then create your outfits top to bottom for each day (sometimes you’ll have 2 outfits), lay them out on the bed, take photos, and then edit. You’ll see where you can double up on a blazer or sweater, so you can remove items. That’s all you need to pack — no more adding in shoes or tops at the last minute. One more tip: I fold my nice tops with tissue paper so they don’t wrinkle. Really works!

5. Follow Coco Chanel’s lead.

After you’ve assembled your packing list, take one or two things out. “Before you leave the house, look in the mirror and take one thing off.” Simplify. Trust me. You know which pieces you will never wear on your trip. Extra suitcase room means possibilities of shopping for new things!

One final tip

When I get home from my trip, I make a list called “What I Actually Wore.” This is a list of what I actually wore and didn’t wear. It helps me learn from my mistakes and plan better next time. If you visit the same place every year, or take similar vacations, this one activity will help you hone your packing skills.

What are your best packing tips?