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Fall and winter walking/hiking - clothes and shoes recommendations?

Hi.  Could use some help.  65 and starting this spring through summer walked average of 90 minutes a day.  Easy being prepared, I think, shorts and tennis shoes.  Now heading into fall and winter I don't want to stop being outside.  Live in Illinois and will travel to norther Illinois, Wisconsin and Iowa.

Any basic recommendations for clothes, shoes etc to get started.

Appreciate the help.



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5 Replies

My biggest piece of advice for you is to dress in layers. Even in the cooler fall I usually have a t-shirt on as my base layer, but may put a long-sleeve shirt, then a primaloft jacket over it. It is easier to adjust to hotter and cooler temperatures if you can add and remove layers. There is also a saying, "cotton kills," so think about synthetic clothing, which is more insulating and warm.

For staying warm, the three most important things to me are my core (an awesome jacket), my feet (socks that keep your feet warm), and gloves.

1. I recommend a good primaloft jacket, preferably with a hood and pockets. 

Primaloft is a synthetic version of down and is much lighter. I had a hard time believing that primaloft would be warm because it was so thin, and was loyal to the much puffier down. That was many years ago. I still love a good down jacket (and have several) but my primaloft jackets are my go-to, and I ALWAYS take one with me when I go out in the fall, even if the weather seems warm. They compress small so they are easy to pack, and they are great for when the weather surprises you and cools down on you! 

I bought an REI-brand primaloft jacket on clearance maybe 10 years ago, and that jacket is so warm, soft, and comfortable that I STILL pack that jacket for cool-weather mountain biking. I had no idea how much I would love it. I also have a Mountain Hardwear, a RAB, and an Outdoor Research, all primaloft, that I really, really love. I would recommend any of those brands! Not all primaloft jackets are equal so compare a few. I have some that are crispy. I have some (all the brands listed above) that are incredibly soft, quiet, warm, and packable if you buy the right one. I like to to have a hood for extra warmth as well. (I do, however, double up and put a down jacket over my primaloft in the dead of winter. My go-to down has been a highly packable Sierra Designs down jacket that I bought off REI many years ago. 

It looks like REI doesn't have a full stock of primaloft jackets yet but the Ghost Whisperer primaloft jacket is on sale in a cool green color and is the first thing I would recommend.

I will mention that I am in Utah. You, being in the Windy City, might care more about also making sure you have a great shell jacket to go over the primaloft. 

2. Warm socks:

I highly recommend investing in good socks for cooler weather. We are extremely partial to Smart Wools (me with wide, flat feet that likes thinner socks) and Thorlos (spouse with high arches and feet that easily blister, who prefers slightly thicker socks) for most of our cool-season sports but I have a favorite trusty pair of REI wool socks that are my go-to for winter snow biking, which is my main winter sport. I can't wear wool anywhere else on my body (it irritates my skin) but have not had any trouble with any of my wool or partial-wool socks in this brand. 

20 years ago, I had an experience with freezing feet while we struggled to start a wet-wood camp fire. I finally, desperately, pulled off my white cotton socks and switched them for a pair of Smart Wools. My feet warmed up in minutes, well before the camp fire started. That experience sold me on the importance of quality and materials (wool/synthetic over cotton).

3. Gloves

My favorite fall gloves are a thin pair of leather Hestras. When it gets realllly cold, I prefer my Sugoi lobster gloves. I also have a 20-year-old pair of Burton mittens that are soooo warm. We both always pack a light pair of REI gloves that we bought years ago, at minimum, when the weather starts to cool. 

I'll stop there ... but definitely for shoes, do a little bit of research. Some shoes are slippery when wet so it's worth it to look for good winter shoe recommendations. In our household, we are partial to Merrell and Keen for our winter boots (and though we do shop at other places too, we both bought these boots from REI). This noteworthy because for both of us, this is the only time we wear that brand. During the rest of the year, I am usually (but not always) in Altras in the mountains unless I'm on a bike.

It's no longer available but it's this is the Keen we love for heavy duty winter:


Location makes a huge difference. I live in Michigan I layer also, during the fall long sleeve undershirt, flannel shirt, outer fleece vest, and hat. Winter month era usally polyester long sleeve undershirt, vest, wool outer shirt or wool pull over, fleece line pants. 
I’m also 65 years old, hunt, hike, winter tent camp.

@tstanley - I'll also throw my voice into the Wool chorus. SmartWool, DarnTough or REI wool socks are what I put on even if its warm and I'm going hiking. They are available in different thicknesses for different temperatures. No clammy feeling at the end of day from sweaty feet, even if the sock is damp when I take it off. I have a couple spare pair, one that I save exclusively for sleeping in, and the other that I will toggle for tomorrows hike.

I recently picked up a Merino long sleeve wool shirt (Smartwool Merino 150 Crew Base Layer apparently I can't include a link even to an REI page...) that I love for hiking in. Even in June in the heat it was super comfortable, wicking moisture away from me and protecting me from the sun, but still keeping me comfortable in the evening when the temps dropped. My wife gives me the side eye for wearing long sleeves in the summer, but the sun protection is worth it to me, and I never felt over warm.

I'm in the middle Atlantic states, but grew up in Central New York, so I'm familiar with cold, wet, slush and snow. I wear Keen Targhee's and love them, very water resistant. No worries slopping through muddy trails, and when we occasionally get snow here, its the boot that I put on.

Already a lot of good recommendations here, but I would also suggest thinking about accessories for fall vs winter.

Everyone is different, but if my hands and neck are cold I am going to feel cold.  Even in the more mild fall temperatures, I like to wear a lightweight pair of gloves, a neck gaiter or scarf, and sometimes ear muffs or a beanie hat.  You’ll want heavier options for the coldest parts of winter, but it’s worth thinking about the “in between” temperatures as well so you can adjust as the seasons change and be comfortable the whole time.


Hi @tstanley .  

Good for you!  Undertaking an exercise regimen and sticking with it requires determination...especially when carrying it through to the less pleasant weather conditions.  

You've received some really good recommendations already, but I'll throw in my 2 cents.

First, I'm in the mid-Atlantic, and we get the whole gamut of weather conditions; hot and humid in the summer; snow, ice, sleet, and "mixed mess" during the winter.  With this being the case, I have quite a wide array of clothing options I choose from.

I agree whole-heartedly with proper layering, and with wool socks.  A couple more specific recommendations though, are that I like liner socks under the wool.  For me, it really helps in the regulation of moisture, and minimizes any itchiness from the wool.  I'm also a big proponent of the mantra "Be bold, start cold."  If I start a hike feeling warm, I need to shed a layer within 15 minutes, or risk overheating and sweating, which will ultimately make you colder and less comfortable.  Even down into the 20s, I will typically wear only a base layer and a fleece, but carry a puffy and/or shell jacket for when I stop or take a break.  Pants that are wind and water resistant are a good suggestion too.  I personally do not like the lined or insulated pants, but choose a good, wicking base layer pant under a standard hiking pant.  My personal favorites are from Outdoor Research, like the Ferrosi or Equinox; or (sorry REI) Eddie Bauer Guide Pro pants.

If you choose to upgrade your winter footwear, make sure you size appropriately to allow room for thicker winter socks.  I prefer waterproof (resistant really) boots.  And if you are in an area that has icy surfaces in the winter, a pair of microspikes might be a wise investment.  

That's all I can think of at the moment, but would be happy to share some more specific recommendations if you'd like.

Keep walking!

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