How to Dress Kids for Outdoor Winter Playtime

Kids would play outside in their summer best on mid-winter days if given the choice.  And while they are actually more prone to heat loss than their bundled up parents, their desire to expend energy regardless of the temperature may actually work to keep them healthier through the winter, as regular activity boosts the immune system.  So parents are left negotiate the fine line between what kids need to wear to stay warm and what they will actually wear. Technology has come a long way since the days of dressing like the Abominable Snowman for winter play, and now parents simply need to know what to buy and how to layer. 

A fleece pullover is easier to clean,
endures harder wear & keeps them
warmer than a sweater.  Zippers allow
for further temperature adjustments.

Building an outdoor-play-worthy winter wardrobe start with "cotton is the fabric of death."  It is a little extreme for just playing outside, but for any layer that will be exposed to the elements, stay away from cotton.  If you plan to be outside for an extended period, especially in the snow or rain, nothing should be cotton, as when wet, it stays wet and keeps moisture against your skin, making you colder.

Layer.  Think of layering as having an adjustable thermostat versus an on/off switch.  This is twice as important with kids who need to be able to take off a layer when they get hot, which they will do even at -20, and you don't want the only layer to be their coat.

Make it comfortable.  Do not get anything that makes them itch, is too tight, or restricts movement, as it is a waste of money, because they will not wear it.

Invest money when necessary.  Winter clothing is not cheap, especially with ever-growing children, but certain pieces are worth the investment.  To make winter essentials more budget=friendly, consider buying at the end of the previous season, a size up, or used.
 
Beyond coat and boots, whose requirements vary by area of the country, below are essential winter wardrobe elements and recommendations for keeping kids warm and parents happy this winter:


Breathable, warm & soft.
Smartwool beanies endure
even the toughest wear.

It doesn't matter what percentage of body heat escapes through the head; put on a hat.  Kids aren't always the biggest fans of hats, but they quickly learn that they will help keep them warm without getting in the way. 
The best hats come down low on the head and should never be made of cotton.  For really cold days or kids with sensitive skin, elect a fleece or fleece-lined hat. For active kids, elect a tight-fitting, breathable beanie, such as by Smartwool.  Though they cover the ears, for a layer of added wind-protection, and the ability to remove the hat during vigorous activity, consider a windproof headband, such as the Barrier headband by Pearl Izumi. 
 

Keep their feet dry and warm.  All kids need rain boots that will allow them to go outside as soon as the rain has passed and expend energy.  No need for investment here, as the goal is to get these shoes as dirty as possible, so make them fun and cheap and turn your kids loose to enjoy them.
What is more important than the rain boots are the socks that go inside them.  Cotton socks are not sufficient for winter on dry or wet days, so invest in wool socks, as they will keep little feet warm and dry.  Wool socks are not cheap but a good pair will last three children through multiple winters each.
These are not your itchy rag-wool socks of yester-year, so do not worry about itching.  Let your kids pick out their favorite design, but consider a tall and thick pair and another with slightly less cushion for the option of wearing them with tennis shoes, as once your kids try them, they will be addicted.  This will also allow for layering on really cold days.    
The most famous brand of wool socks is Smartwool, as they have an incredible variety.  You can pick them up at REI, where if you buy 3 or more pairs of socks, they are 10% off.  REI also has a high quality private label that offers a considerable savings, but they do not have as many design choices.

Choose a good base layer.  Base layers sit next to the skin and should wick moisture, such as sweat, which kids will still do on the coldest days, away from the body.  They should also dry quickly.  The best materials for base layers for kids are polypropylene, capilene, merino wool, or fleece.  Most companies make their long underwear in a variety of weights, so to make the pieces go further, choose an appropriate weight for your average winter temperature, not the extremes, and consider style and comfort so that the piece can be a wardrobe staple not a drawer liner.  
Above the base layer is an insulating layer, and there is no better or more kid-friendly insulator than fleece, as it wears hard and washes easily.  Consider two essential fleece pieces; first, a thinner, straight-cut piece such as the North Face's Glacier pullover or LL Bean's Fitness Fleece.  Both can work as an insulating layer in milder temps or as a mid- or even base layer on cold days.  Next comes a thicker, more wind-resistance fleece, such as Patagonia's Snap-T pullover or Synchilla jacket, which may work as a winter coat in milder climates.       

Perfect for layering, vests keep the
core warm without limiting arm
movement.

The most important area to keep warm is their core, and there is no better layer than a vest.  Vests were made with kids in mind, as it is impossible for them to confine movement.  A vest made of a dense fleece is less bulky under a water/wind proof shell than the "puffy" or down vests, which also carry a bulkier price tag.
These vests are available through many retailers, but if buying from a retailer that does not specialize in outdoor clothing, make sure to read the tag, as they frequently slip in cotton.

There are many ways to make a winter wardrobe more affordable, but my favorites are 1) Join REI and shop there.  REI is a co-op, and a lifetime membership is only $20.  If you do any form of outdoor sport or you just like fleece, you will save a great deal by joining, especially if you make any major purchases through REI, such as a stroller, bike trailer, or a first bike.  2) E-bay.  Outdoor clothing is meant to be long-lasting, and generally even children cannot destroy it, so try getting some gently used items.