Transitional Season Travel: You just never know

The long range forecast tells you one thing -- but you get something entirely different! On a recent trip to Ontario, I experienced this twice. I spent the first few days near Toronto with my brother, where the weather was much colder and windier than predicted, and despite having packed layers, I nearly froze on our lakeside walks  Next came a dressy-ish evening work event in Toronto. I wore a "suit" of my blue knit jacket, silk blouse, blue wide legs, raincoat, and cream boots and felt appropriately and comfortably dressed for the occasion.  Then I left for Kingston for more work and visits with friends. There, the weather was a balmy 18-21 and sunny most of the time, and I was often too warm! 

Still, it was glorious to walk along the lake and check out the autumn colours. 

I took a leaf from Dee and aimed for the 3x3 capsule (3 bottoms, 3 tops, 3 toppers -- aside from activewear) but in the end I added more mid-layers (i.e. sweaters), and was glad I did. 

The new boots were excellent for comfort except for when I wished I had something other than boots.  The runners are my active-wear ones, meant for long walks or hikes or jogs, not fashion. But because my only other choice of footwear was ankle covering, I was often too warm and and had to rely on the sneakers in a few situations where they didn't look particularly good with the bottoms. I wish I'd brought my blue oxfords instead. The velvet pants were also not the best choice.

Oh well -- live and learn -- maybe? 

How do you manage packing for transitional weather? Any great (or awful) experiences to share? 

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17 Comments

  • Rock replied 2 months ago

    Ooh I sympathize with you, Suz.  About two years ago I went to Chicago in the spring,  The forecast was for lovely weather, but it was freezing and windy as is typical for Chicago.  I froze for ten days.  Now I vow to not be too trusting of the forecast.  


    In about four weeks, I’m going to New Orleans, Tokyo, and Taiwan in one extended trip.  Part of the trip will involve work suiting, part will be sightseeing in cold weather, and part will be pleasant weather in Taiwan.  I’m planning to bring several HeatTech tops and two t-shirts to layer under lightweight, low volume solid color merino or alpaca sweaters.  I plan to bring two toppers, one a lightweight puffer and one a rain jacket.  I will also bring a blazer for work events, and a puffer vest. The layers should provide lots of options for changes in weather.

    i will bring one denim pant, one ponte pant that can fake it with a blazer, and a couple of lightweight crops.  I plan to purchase a new pair of HeatTech bottoms in Tokyo.

    Typically I bring one pair of dark colored booties and one pair of sneakers, with varying weights of merino socks, and  one or two scarves.

    I think it is always live and learn, but I try to re-evaluate and refine my layering pieces each trip.  Chicago is one of my favorite cities and I never want to have another miserable trip because I was unprepared.

  • Katerina replied 2 months ago

    Suz, I am with you. It is a challenging time of year for packing. My biggest issue is that I always overpack no matter the season and so I actively work on it every time I travel. Transitional seasons, fall especially, make this much more difficult because I try to cover all the bases and bring too much stuff. I usually bring a bigger suitcase than everyone else in our group, which is not only impractical , but sometimes a bit embarrassing.

  • Lisa replied 2 months ago

    Beautiful pictures! 

    Traveling is always a struggle to get the "right" wardrobe. The weather can change at any moment! My biggest issue with travel used to be footwear. Many years ago I made the mistake of wearing ballet flats with no socks for a day of sightseeing in London. I had so many blisters I bought a pair of knee high London printed socks that I wore with the ballet flats. I looked ridiculous but my hurting feet did not care. I've never worn ballet flats without a foot ped or other sock since and don't even have them in my wardrobe anymore. My feet sweat and rub if they don't get enough ventilation with my shoes if I go sockless.

  • ChristelJ replied 2 months ago

    It seems every trip gives me a learning experience like that, so I relate. When I have had a host, I have borrowed puffers and such when necessary. I try to include plenty of layering pieces, but even then they can be inadequate for harsh weather.

    I feel your regret at not having your blue oxfords. Of course footwear has to be comfy for walking, but what about proper function for pant length? I have packed the wrong match-up, resulting in unseemly gaps I had to live with all day.
    Now I do a pre-pack several days ahead, and try on every pant with every shoe...

  • Dee replied 2 months ago

    Yes there was a weird swing in temperatures recently here in Eastern Canada, and that certainly does make it difficult to pack for.

    I’m a chronic over-packer most of the time and on my recent trip to England I really wanted to just do carry-on only. I wasn’t exactly sure how I would be able to do this but then I saw the 3x3 packing grid online which helped get me started on a colour palette and coordinate some outfits to mix and match together. However, I also wore an additional outfit for the plane with a heavier jacket overtop and also added a couple of extra tees and a lightweight packable rain jacket that easily tucked into my bag along with a couple of different types of scarves.

    So in reality I had 6 tops to wear, as well as 2 outerwear options,  4 toppers, and 4 pants because of what I wore on the plane. It was quite cold when I first arrived and I had started to wonder if I should have packed more longer sleeved tops instead, but then the weather warmed up nicely and it all worked out quite well in the end.

  • JAileen replied 2 months ago

    Oh no!  I hate being cold.  Years ago we went to Boston in late fall.  We had lived in a ski area so I thought I knew cold.  Ha!  Joke was on me.  My outerwear was completely inadequate.  The result was that I had to wear a pullover sweater I had packed every single day.  I was pretty sick of it by the time we got home, and never wore it again.

  • Suz replied 2 months ago

    Thanks for the commiseration, all. I'm glad I'm not alone. Good strategies to borrow from hosts if possible, or to purchase something while there. I have done the latter from time to time, for sure! Borrowing a coat from my brother would not have worked, alas, as we are no where near the same size. ;) 

    I tend to overpack a bit, too, and strangely, even on this trip felt I had overpacked some items while under-packing others! It's probably a kind of lesson from the universe because following our London trip I was feeling so smug about my packing prowress -- on that trip, I had exactly the right clothing for all situations that arose and wore almost everything at least once -- maybe had one top or something that I didn't end up putting on, but everything else went through its paces. 

    Oh well!  

  • Jules replied 2 months ago

    As a transitional season traveler I hear ya! I was in Paris in March 2023 and we are headed to Amsterdam on Friday, with a side trip to an outdoor festival in Germany. Thanks for posting this to get my gears going about packing. The first thing that's occurring to me is to bring the wool beret and scarf I picked up in Paris -  because even if the forecast appears temperate and dry, one can experience an entire season's worth of weather in one day of city walking, and warm accessories that easily come off and on are a godsend. The scarf will function as a plane blanket as well.

  • Bonnie replied 2 months ago

    We went to Italy in April a few years ago and I planned to purchase a sun hat while there because I am really sensitive to being in the sun. Last trip was in June and there were sun hats everywhere so no problem, right? 

  • Angie replied 2 months ago

    GORGEOUS Autumn pics!

    That sodding inaccurate weather forecast that ruins our well thought out travel capsule. URGH :(

    You made it work and looked fabulous nonetheless! 

    Transitional weather can be all over the place. Like you need to pack your Summer shoes and a beanie....

  • Sal replied 2 months ago

    What beautiful autumnal colours!!

    Yes transitional weather is very hard and weather forecasts are often not correct!!  Especially in NZ.  

    I have got it wrong on several occasions - December can be cooler than expected and I recall needing a puffer on the 24th December which I had not packed.  Likewise in Ohio last year my closet was a bit too wintery when the temperatures were very warm during the day.

    My only real recommendation is merino tanks or layering tops like heat tech that can be worn under a shirt to make it warmer or not worn but don't take up much room.

  • Runcarla replied 2 months ago

    I swear by super lightweight puffers (what are being called ‘liner jackets’ recently) and under layers (which can be worn - or not).  


    Travelling on shoulder seasons has its benefits (no crowds, better prices) however the weather can be a roll of the dice!  The last trip to the UK I decided last minute to not bring boots, and subbed in a second pair of sneakers instead.  It turned out to be the right decision!

    The trickiest conditions, in my opinion, are cool/cold mornings and evenings with hot daytime temps.  Layers, layers, layers - and a backpack to carry them all around!  

  • Irina replied 2 months ago

    You really need knitted Cole Haan oxfords in navy blue!
    I wore my black pair a lot on my recent trip to Portugal. I found that I do OK packing for a week long trips but with two weeks it gets harder to predict weather anywhere. On my recent trip, I didn’t wear my lightweight Zara jacket in Lisbon. It was either too warm for it during the day or too cold in the evenings. Oh, well. Not too terrible. I remember putting layers, socks, my cotton mac, a scarf and feeling so cold on a boat in Venice. Or rushing to a H&M in Prague to buy a sweater and a hat. Also, being cold and wet on a rainy day in Paris. Hmm, there is a theme here. I often travel in October :)

  • Suz replied 2 months ago

    Irina, I HAVE those oxfords! I wish I brought them. I wore them constantly in the UK. I just didn't think it would be warm enough for them in Ontario. Big mistake! 

    And yes, maybe my biggest mistake was travelling in October, LOL! 

    I did bring merino underlayers (not pictured) and I wore them. I also had my lightweight puffer. But Carla, you are right that it was the temperature variation within a day that made things even more complicated. 

    Sal, it sounds like you've been caught with too warm items on a trip as well. I seem to remember that last year from your report. 

    Jules, definitely bring a hat and gloves for Europe. They don't take up a lot of room and could come in very handy indeed. 

    Irina, I think you are right that when a trip is longer, it's just harder to pack. I was gone for 11 days, so not quite 2 weeks but long enough. 

  • Jaime replied 2 months ago

    Beautiful pictures Suz! I have no great packing suggestions - but there are some good ones above. My focus is usually on comfortable shoes and a few layers and I often end up repeating outfits a lot on trips because only one really suits the weather.

  • Firecracker (Sharan) replied 2 months ago

    I can only sympathize. It sounds like you had the gamut in weather, very hard to pack for! Beautiful photos, though! And I consider it a big win that you felt good in what you wore to the evening work event.

  • RobinF replied 2 months ago

    Beautiful walks!

    We also do a lot of our travel in September and October, which is a nice time of year for it but also can be hard to pack for. This year we didn't do an international trip but went to Salt Lake City to visit our daughter and it was hot summer weather! Shorts and tees. But we have been to Amsterdam and London in September and wore puffers. 

    I feel your pain about not having the right shoes - I have been known to buy some on a trip :)

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