Planning My Fall Travel Wardrobe

Oh, my friends… time is ticking down. Is that the expression I want? Gad. I’ve been using malapropisms and mixing my metaphors all week. It’s a function of my excitement I guess. We leave in three days for almost a month in Portugal and Spain.

After we came home from New Brunswick in late August, I laid out my plans for trip preparation in neatly planned chunks of time. The weeks were supposed to unfurl gently and uniformly following my designated pattern.

One week was for shopping. I needed a few things before we travelled. On my last trip, to Calgary in July, I held my breath hoping that my old suitcase would not burst open on the luggage carousel. It’s given me good service for many years and many, many miles. And now it’s time to retire it. After a few forays into the city, I finally found a suitcase I liked. And last week found a tote bag/overnight bag to use as my carry-on.

Other weeks were set aside to review all of the planning we did last spring, print off any documents we needed, make sure we had copies of all our confirmations, make final our trip calendar, get the housesitting arrangements in place, plus do some lawyer stuff that we’ve been putting off. And plan my fall travel wardrobe.

Of course my well laid plans required some massaging and a bit of squishing because of a few minor health issues: I had an eye infection one week, the next week I was stung by a wasp and my arm swelled up like the incredible hulk. I do NOT react well to insect bites or stings. I’ve been bitten and reacted badly on four continents, people. Let’s just say that my travel first aid kit is quite robust. After my eye and my arm cleared up I still had a couple of days each week to do my trip errands. Then I caught a bad cold and was further sidelined for a few days. Good thing I started getting ready early.

The last thing I had to finish was planning my travel wardrobe. I’ve been working on it bit by bit over the last couple of weeks. And I thought I’d explain my process today.

It’s not rocket science. I don’t use a formula. I’ve tried, but it seems that hard and fast numbers or rigid rules don’t work for me. Probably because wardrobes and style preferences, not to mention travel plans, are individual.

For a while, I thought I’d try the “sudoku packing method.” It looked interesting. In this method you’re supposed to lay your nine pieces out in a grid, three tops, three bottoms, and three layering pieces. And be able to work back and forth, and up and down the grid to build outfits. Like a game of tic-tac-toe. You can read about that method here.

But upon closer consideration the idea of packing the same number of bottoms, tops, and third pieces or layering pieces did not seem sustainable to me. I rarely travel with more than one or two layering pieces. A jacket that goes with all my bottoms, and an additional rain jacket for hiking. And I need more than three tops. So I shelved the sudoku method pretty quickly.

And I went back to my own way of planning. I started with the bottoms I wanted to take. Then I added tees or light sweaters and footwear with each bottom to create outfits. I used the same tops and footwear with each bottom. Or I attempted to do so. I tried on each outfit, setting aside the pieces that worked. Then I eliminated bottoms that did not work with enough of the tops. And tops that didn’t work with the bottoms that I’d planned to pack.

Like my All Saints tan linen cargo pants. I’d planned to pack these because they are great for hot weather. But I wasn’t loving them with any of the tops that worked well with the other bottoms. They had to go. Ditto a long-sleeved striped tee and a long-sleeved white tee and a yellow tee and sweater combination that only worked with the All Saints cargos.

I annotated my lists. See below. And I added new options, like my white Levi’s, and noted decisions I needed to make. Then I was done for the day. Trying on outfits is exhausting; for every one you love there will be a couple you hate. Besides, the room looked like a bomb had gone off, and I was in desperate need of a cup of tea. I restored order and went to switch the kettle on.

A couple of days later I tried again. Fall travel wardrobe attempt #2. I listed the tops and bottoms according to whether they were more suitable for warm/hot weather or for cooler temperatures. I noted some pieces that were iffy, and then crossed them out or checked them off once I’d made a decision.

My white Levi’s 501s were in, and the black linen dress I’d planned to pack was out. I tried everything on again and asked myself if I’d really and truly wear that outfit. The dress was a definite no. I’d thought about packing my Stuart Weitzman black mesh Mary Janes but decided that they were not comfortable enough to walk for any distance, plus I’d probably ruin them.

I debated packing my wide-leg Levi’s like I did last year, but decided against them. They are bulky to pack and too hot to wear all day. I decided to bring my cropped mom jeans. I bought these second-hand two years ago. They are loose and comfy and good for warmer days. Plus I’m going through a period where I love wearing them. Their loose, easy, insouciance suits my mood these days. I mean if a pair of jeans can be insouciant, that is.

See annotated list number two below.

Then after a brief interval waiting for my cold to pass, attending lawyer’s appointments, and hair and pedicure appointments, I finally finalized my list. Fall travel wardrobe… the conclusion.

I once again started with the four bottoms I would be packing. Using the tops I’d planned to pack (black and white tee shirts, light sweaters, linen shirt, and navy sweatshirt) and the footwear I’d have with me, I made a list of outfits. See below left. Each bottom made at least three different outfits. I found I could even spin my navy and white checked Rag and Bone cropped pants into five different outfits. There’s no way I will need sixteen different outfits. I will probably repeat a few of them more than others. I could probably eliminate one pair of pants altogether if I wanted to be strict with myself. But I don’t. Want to be strict with myself, I mean.

I also decided on a travel outfit. I needed a pair of comfortable long pants. Comfortable enough to wear on the plane and long enough to wear with socks. I’m always cold on planes and I need to wear cosy socks. I can never understand how some women travel in cropped pants and flip flops. Plus, I will need a pair of long pants in case we have a rainy, cool day on the trip. I decided to wear my Mother long, stretchy, black jeans with my pink Vince cashmere sweater and my black Uniqlo windbreaker. I’ll bring my plaid Burberry scarf, and probably throw another scarf in my luggage.

You can see my final list below. I rated my tops and bottoms for suitability for warm or cool weather. That might have been overkill. But, I love lists.

You can see the pieces I’m packing, below, laid out on the spare room bed.

Starting from the left, and top to bottom. I’m packing four bottoms. My Cos black cotton wide-leg, cropped pants, my checked Rag and Bone cropped pants, white Levi’s 501 jeans, my cropped Mom jeans. Altogether I’ll be packing 9 tops. My Max Mara white linen oversized shirt. Two light-weight long-sleeve sweaters: one black, one burgundy. One short-sleeve black and white striped sweater. Four short-sleeve tee shirts: one good white one, one old white one to wear hiking or under sweaters, one good black one, and one old one for hiking or wearing around the accommodation. We are staying in several self-catering places. I won’t wear my good tees to cook in or when lounging about with my tea and a book. And I’m packing a navy sweatshirt for cool mornings.

I’m also packing some specialty pieces: light-weight sweats and shorts for hiking, a light-weight walking/running shirt. My bathing suit. And a waterproof jacket for hiking or on cool rainy days, if we have any.

I’ll pack my black Birkenstocks, and a pair of cream and navy Adidas Spezial sneakers that I bought a few weeks ago. I’ve decided that I cannot travel with my Veja sneakers anymore. They are too heavy and hot. I’ll also pack my black running shoes that I wear for walking and hiking. I’m leaving my hiking boots at home. I’ll wear my burgundy Paul Green loafers on the plane.

Of course I’ll also be packing nightwear, and underwear and socks, and a pair of ski underwear bottoms for lounging in. Underwear bottoms make great leggings. And they’re more comfortable. I plan to throw in a soft hoodie for cool mornings or evenings. The only non-athletic jacket I’m taking is my black Uniqlo windbreaker. It did yeoman service last year, and I expect it will again this year.

Anyway. That’s it. I think by the time I’m eighty I will have my travel packing down to a science. Like when my mum and my father were first married and had moved with his work several times in two years. Mum said that if anyone mentioned moving, the dishes stood to attention in the cupboard all ready to be wrapped and packed. Again.

It seems that every year I bring something on our trip that I wished I’d left at home. In 2019 it was my boot cut jeans. Why, oh why did I pack them? I wore them one day. Or my burgundy down vest last year. I wore it faithfully for several years, and so last year I packed it almost without thinking. I wore it once. It’s not coming with us this year.

Sometimes I conjure up outfits just for the sake of being flexible and, when I get where we’re going, never wear them. This year, when I tried on an outfit, I asked myself if I’d wear it at home.

That helped me to eliminate several pieces. And trying on is key, my friends. I thought about bringing my striped oversized shirt. I could wear it under my black sweater, I told myself. Until I tried it on. Nope. I’d forgotten how much I hate fussing with a sweater over a long-sleeve shirt. I also found the second try-on was helpful. I tried on all the combinations I thought had worked the first time. If I said, “Oh, yeah.” They made the cut. If I demurred they didn’t.

So now everything has been washed and ironed and folded neatly in their respective piles. My pile, and Hubby’s pile. Tomorrow I’ll divide up the piles so that some of each of our clothes goes in each suitcase. We travel with carry-on size suitcases, but we always check them. A change of clothes will go in our actual carry-on luggage. I will take my new tote bag, and Hubby always brings a backpack. I still have lots of small last minute stuff, chargers, converters, ipads, my journal etc to pack. Plus cosmetics, drugs, first-aid kit, hats, sunglasses… you know.

Then after everything is packed, there’s just the waiting. Sometimes I think that’s the hardest part.

I’m hoping to be able to blog when we’re away. It all depends on where we are. I fear that Saturday will be a bad day for blogging for most of the trip. Maybe a mid-week post might be welcome?

Still, I’ll post on Instagram probably most days. But as always, I’ll save the best stories for the blog.

Now it’s your turn, my friends. Any good travel packing stories you want to share with us? Or packing disasters. Sometimes disasters make the best stories.

P.S. I didn’t take travel outfit photos this year. But you can see previous travel packing posts here and here if you’re interested. Some of the pieces you’ll recognize, I imagine.

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