If you haven’t already felt a chill in the air, you will soon. As we approach Thanksgiving here in Canada, temperatures begin to drop below freezing for much of the country. We’ve already seen a couple of nights below zero here, with the temperature generally ranging from 1° – 2° Celsius to 14° Celsius over the course of the day.

With such a range of temperatures, there are some unique challenges. I’m going to focus on clothing & how to tote it all around. This was a particular challenge for me, so I’m sure it’s something that’s come up for others as well.

The Right Kid’s Clothing for the Temperature

There’s going to be a lot of clothing. You’ll need to crack out long sleeved shirts and pants for the kids. And if that weren’t enough, you’ll need sweaters, jackets (wind & waterproof recommended), toques, and mittens or gloves. A regular hat for when the temperature peaks will be important, as it typically grows too hot for a toque.

Where I am, it’s a wet Fall, with almost as much rain as we typically see during the Spring. As a result, rubber boots are a necessity, but they do nothing to keep kids feet warm. This makes it especially important to double-up the socks at the start of the day. Remove the extra set by midday. Although you’ll likely want to swap out both pairs, as they’re likely soaked from jumping in muddy puddles.

Clothing Checklist

  • Long-sleeved shirt (2 – worn & packed)
  • Pants (2 – worn & packed)
  • Sweater (1)
  • Fall Jacket (1)
  • Toque (2 – they’ll likely lose 1 or get it very wet & dirty)
  • Hat (1 – to be put on as it gets to warm for a toque)
  • Mittens/Gloves (2 pairs – and they’ll likely lose 1 hand of each pair, hopefully not the same hand)
  • Rubber Boots (1 pair)
  • Socks (4 pairs – double up at the start of the day, swap out over the course of the day)
  • Sunglasses (optional, but recommended)

This list is really just the bare minimum. It doesn’t take into account anything special, like if they’ll be playing soccer or football, which come with another set of clothes, including shoes. If the temperature ranges warmer, you may wish to consider a pair of shorts and short-sleeved shirt. This isn’t typically an issue this late in the fall, but stranger things have happened.

How do you carry it all?

Even if you were able to find a baby-bag that wasn’t overly feminine, chances are your kids have long outgrown it. When my wife is takes the kids out, she upgrades from a “phone-wallet” to a “kitchen-sink” purse. Unfortunately, that really isn’t an option for most men. Some might be able to get away with it, in some cities, but things trend a little more conservative here.

There are three options that really stand out: duffel bag, backpack, or a messenger bag.

Duffel Bag

A duffel bag is certainly big enough for everything you’re going to carry. In addition to the long list of temperature-appropriate clothing, you’ll need all the regular stuff (including the spare lovey). With a pocket at either end, and usually a smallish one on the side, there is some ability to organize, but not much.

You’ll want drinks & snacks at one end. Quick toys, spare lovey, and other “occupiers” at the other. Tickets, passes, wallet, and phone will likely go in the side pocket. Don’t keep these in your pants. It becomes very awkward when you’re holding one kid’s hand and trying to balance a swinging duffel while you reach for your (inevitably) cross-body pocket. Trust me, this is not considered a good yoga posture.

The top benefit of a duffel bag is its storage capacity. A fair-sized duffel beats out most backpacks and all messenger bags. Making the duffel bag ideal if you’re taking the kids to soccer, or if you need to lug extra supplies.

The Downside of the Duffel Bag

Sadly, the duffel bag’s large, main storage area is also its biggest weakness, as it typically offers no sorting capability. It’s literally one big section. This means everything gets mixed up and bounced around, no matter how well you try to keep things organized. If you only have clothing for one kid, it’s not a big deal, as you’ll have a plastic bag for anything soiled. But you’re in real trouble if there’s more than one kid. Trouble can also arise from sports gear, diapers, wipes, picnic goods, etc. Additionally, if the temperature stays cool, your fingers will get frosty before you can sort through everything. So keep that in mind.

An additional drawback with a duffel bag: shopping. Far too many stores require people to check/leave their bags and backpacks at the front before they enter the store. Although this never seems to apply to a purse or a baby bag, it always applies to a Duffel Bag or Backpack.


One of the premium offerings, the backpack has numerous different pockets making it easy to sort everything for quicker retrieval. Most backpacks have 2 or 3 large pockets (one of which is typically padded to protect a laptop or tablet). Add 2 or 3 smaller pockets on top of those. If you’re lucky, there’s a small pouch dangling inside of of the larger pockets. Sometimes there are places to put pens, a small notepad, and a few other small items at the very front.

Additionally, most backpacks have a bottle pouch on either side. There may even be another pouch, typically big enough for small battery charger or mp3 player (if you still have one of those). If you’re really lucky, there’s a flat pouch that rests directly against your back. This is ideal for important documents, tickets, etc. Some backpacks also have laces, clips, or velcro straps, which you can to attach a plastic bag or shoes.

If we’re talking about convenience, this is definitely a great option. There’s plenty of space for everything you need for a typical day. There’s also plenty of options for how you want to have it sorted to be suit your family’s needs. If all the straps are adjusted correctly (including a chest strap), the backpack is one of the most comfortable bags you can wear over a long period (especially if you’re hiking).

The Downside of the Backpack

As mentioned when discussing Duffel Bags, you may be forced to abandon your supplies. If there’s a “No Bags” policy, they’re very militant on taking away your backpack. If you have multiple kids, and one of them is very small, you will not be able to wear them. You could wear the backpack on your front. From my experience however, this is more awkward and difficult than it’s worth.

Messenger Bag

Of these three options, the Messenger Bag has the least amount of storage space. If you aren’t great at packing things, the messenger bag is not for you.

Typically, a messenger bag has two larger pockets, plus a handful of pockets of various sizes, safely beneath the flap. Sometimes there’s pocket in the flap, and another large one on the back of the messenger bag. Additionally, there may be 1 or 2 bottle holders and small pockets on either end.

Although typically not as comfortable as backpack, Messenger Bags have 1 huge advantage: quick access. When worn right, you can slide the bag from your back to your front without ever taking it off.

If that sounds somewhat like a baby bag, there’s a reason for that. Many baby bags are (typically smaller) messenger bags. To make a messenger bag actually work well though, there’s a few things you’re going to want to do.

Messenger Bag tips
  1. Don’t fold your kid’s clothing, roll it. You can actually compress it a lot smaller this way. Plus, by storing it “end up” you’ll have an easier time retrieving it from the bag when you need it. Given the range in temperature, this is going to be vital.
  2. Tighten the strap. A messenger bag should not hang next to your body (like a duffel bag or purse). It should be tight across your back. Leave it loose enough that you can pull the bag from your back to your front without pulling it over your head. If this description leaves you scratching your head, I highly recommend this article on messengerbags.com. Their article has has a few great pictures to demonstrate.
  3. In an easy-to-see colour, write “kid’s bag” in big letters on a visible part of the strap. Shockingly, by looking similar to a baby bag and that label, most stores let you ignore the “no bags” policy. This is especially handy when you’re in aisle 5 and your toddler starts screaming for goldfish…


Of the three, messenger bags are my preferred option for toting around the kids stuff on a day out in the fall. With such a range of temperature, you’re need to put away or swap out that long list of clothing quickly. Quite often, there just won’t be anywhere to put your bag while you do it. This makes the messenger bag essential for fall outings.

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