How To: Dress for Fall Cycling

Welcome, Autumn! This is my favorite season with the best cycling weather.

Fall cycling: light jacket and tights

Fall cycling: light jacket and tights

Incomprehensibly, when summer ends bike commuters begin dropping off as if they were flies and the crisp autumn air were infused with Raid. I’ll never understand why so many people think the best days to cycle are the insufferably hot ones. In light of this phenomenon, we’d like to discuss how to keep on cycling in the fall. The main trick is using light layers to combat the chill that you can remove easily if your body warms up. I am writing this from my point of view cycling in Chicago. If you live in an area with mild weather, consider this your how to dress in winter advice, or pick-and-choose what works for you.

  • Gloves – Start carrying light gloves with you. Even if the weather’s not particularly cold, your hands will be cold exposed to the wind on the handlebars.
  • Earmuffs – Like hands, ears get cold quickly. As soon as a chill is in the air, muffs are on my ears.
  • Scarves – A scarf around your neck works to keep the chill away. If you get too hot, it’s easy to remove. Remember to wrap it well. If it is too long, it risks getting caught in your spokes or a passing car’s mirror!
  • Socks – If you’ve been wearing sandals all summer, add some socks underneath or change your shoes completely. For the first few weeks of fall last year, I wore Smart Wool socks under my Keen cycling sandals for my work commute. Sure, you may look a bit dweeby, but your little piggies will thank you.
  • Boots – Boot season is fun! Enjoy it. In Chicago, for longer rides I can wear my stylish boots only in the fall. By winter, I’m stuck with my sturdy and serious black leather boots from Russia.
  • Jackets – A light button or zip down jacket should do the job admirably. Jean jackets are perfect, as long as you’re not wearing jeans on bottom :) If you need a bit more movement, a windbreaker or cardigan may be better. I don’t wear sweaters if I think I will warm up because I can’t take them off over my helmet. I’ve made that mistake before and entertained pedestrians by wiggling around while blinded by a sweater (luckily, I stopped riding first).
  • Shorts, Skirts and Dresses – I wear shorts, skirts and dresses well into the fall. Remember that legs don’t get as cold and warm up quickly with pedaling. Unlike a sweater, you (usually) can’t easily take off your pants when you get hot. I’d much rather be a bit chilly on my legs for the first few minutes than be miserable and sweaty.
  • Arm and Leg Warmers – These look really cool and are a good solution to cold legs. I’ve never tried them before, but they’re worth looking into.
  • Tights – I get very excited about tight season. Have a ball wearing fun patterned and colored tights. This is a great way to stop worrying about your skirt staying in place.
  • Leaves – As pretty as they are, watch out for fallen leaves. They are slippery when wet and mushy.
  • Lights – You must use lights on your bike (white in the front, red in the rear).  This is even more important in the fall, when it is darker longer.

That’s it. Most of the time you can simply wear what you would wear off the bike, but some parts of you will be colder and some parts of you will be warmer. Remembering to cover your extremities and having easy to remove layers will make your life a lot more comfortable.

Don’t stop riding – the fun’s just beginning! Celebrate your new sweat-free existence. We’ll start our winter “how to” series soon :)

Mr. Dottie in fall-colored zip down wool

Mr. Dottie in fall-colored zip down wool

  • Lovely Bicycle!

    Autumn weather is the best, and I love tights and boots – so I’ve really been looking forward to it. This will be my first Fall/Winter season cycling. Not sure yet whether I will be able to make it all the way through the winter, but we’ll see!

    • dottie

      That’s a smart approach to take. Last year I was not sure what I would do about winter and simply took it one day at a time. I learned to adjust and never stopped (except on the worst days) but not pressuring myself into doing something that felt dangerous or uncomfortable was important to the process. There’s no shame in putting away the bike for the winter, as long as you give it a try first.

  • Catherine

    “Tweed” and “wool” are among my favorite words in the English language. And I am convinced that the most soothing feeling on earth is a gently worn and slightly pilly flannel sheet against a cheek. Ah, fall. That’s about all I have to add to this discussion :)

  • ksteinhoff
    • Daniel M. Perez (Slow Bike Miami)

      You got that 100% right!

  • Cyclin’ Missy

    Would you mind doing a rain riding guide, too? Thanks!

    • dottie

      Great idea, Missy! I’ve talked about cycling in the rain a bit here and here (and a bit more if you click on the “rain” tag to the right) but a full guide is definitely in order.

  • superbk

    I am SO excited for my first Fall as a bike commuter. Last year I walked to work everyday, but now I can wear all my pretty shoes on the bike, including my favorite boots! And tights! And skirts! Oh my!

    Luckily, the snow is minimal in DC, so I should be able to bike-commute well into winter while still wearing regular boots, although the earbags sound like a dream!

  • E A

    dottie, you’re right – layers are key! On my morning commute (especially in the sun) I could be fine in a long sleeve shirt, but by the time I ride home at dusk or later, a light jacket is sometimes needed. Also – I can’t stress how important and useful being well-lit is! Too many cyclists ride without the necessary lighting — and in Chicago it’s the law!

  • Doohickie

    I hope you don’t mind, Dottie, but I pointed to this post from my blog.

    Well said.

  • Scott

    I think most people in Chicago have completely the wrong idea about cycling weather. They think it is too cold most of the year, and only ride when it is incredibly hot. Then they say they can’t do it because they will be too sweaty. A guy I work for tried it once this year (on a 94 degree day of course), and decided he can’t do it. He asked me whether I sweat through my clothes every day. I didn’t know what to say.

    Well, here’s to awesome riding weather and plenty of open spaces on the bike rack!

  • Lara

    Perfect list…thank you. The weather here in Boston is getting crisp and cool, and I’ve been layering up slowly. Love riding in the Fall and Spring…

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  • Jess

    Can anyone give any suggestions on bottoms to wear cycling? My usual commuting gear is more typical cycling gear: lycra pants, light tshirt and a lightweight and waterproof jacket with plenty of ventilation.

    But when I want to go into town and wear something ‘normal’ during Fall and Winter, I am at a loss what to wear.

    I have ruined countless pairs of jeans because the thigh area wore thin from biking in them, but would like to look normal and be warm while cycling and wandering around in shops!

    • dottie

      Hi Jess. I can’t say enough about my love for cycling in skirts and tights. The skirts allow for freedom of movement and the tights keep your legs warm and your modesty intact. Another love of mine for winter cycling is wide-leg jeans, although you’ll need either an ankle strap or chain guard to keep your hem clean. The looseness in the thigh area should prevent any undue stress on the fabric.

      • Jess

        Hmm, thanks for the advice on wide leg jeans, I’ll keep an eye out for a pair.

        I felt so silly asking that question because I’ve been bike commuting for 4 years due to not owning a car. But I’ve also seen countless, irreplaceable favorite pairs of capris and jeans bite the dust due to biking into town with them!

  • Braxton

    Mr. Dottie and I appear to wear the same cycling gloves.

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  • Daniel M. Perez (Slow Bike Miami)

    I’ll shut up about Fall in Miami. Seriously, I will. ;-)

  • Yvette (Slow Bike Miami wife contingent)

    You’re so lucky to have such a thing as “fall” (and not have it mean you hitting the ground). Waiting for the heat to abate here so I can wear tights again and forget about my skirt staying in place or not.

  • Sungsu

    I use lights in the daytime when it’s overcast and rainy.

  • Trisha

    My ears get sore! I haven’t figured out how to avoid this yet, other than perhaps wearing earmuffs or getting one of those flap helmets.

    Dresses, tights and boots are the best fall cycling uniform. ;)

  • Charlotte

    I’m a HUGE fan of cycling with earbags.

    Really. They’re the best.

  • E A

    Trisha, I usually keep a gator (my preference is the HAD headwear — The tube style allows for so many different ways to wear it – and it’s thin enough for cool fall or to layer in the colder winter months.

  • Trisha

    How have I never heard of this product? they look great on you. :)

  • E A

    Great idea! I think I’ll look into these this fall/winter!

  • cupcakerator

    I’m so excited for fall riding! And fall fashion, of course.

    I’m in love with dresses, tights, and boots. I can’t shut up about them.

    I just worry since my throat has this uncanny ability to get sore when I ride in windy weather at all. I wish I could avoid this somehow.

  • Mamavee

    I love it- ya’ll read my mind as I have been thinking about fall riding. And I love the jean jacket comment. I love my jean jacket but finally found the perfect jacket to wear with jeans ( not jean of course! purple velvet!)

    I need to wear skirts more too as I hate the hot legs feeling. and I need to buy some leg warmers.

  • cratedigger66

    what you don’t like the 80s style “jeans suit?”

    “Jean jackets are perfect, as long as you’re not wearing jeans on bottom :)”

    seriously, I enjoyed my short ride yesterday, which was the first one of season where the leaves were noticeably crunching under the Raleigh tyres.

  • Trisha

    Ooh, we will definitely need to see pictures of the purple velvet jacket!

  • miss sarah

    Yay! I love fall too. And yes, I hate how unforgiving the snow is to my pretty boots. I basically have to get synthetic plastic ones that don’t get all battered from the moisture. Fall is indeed the time.

    I also like tights because I can then wear short skirts without worrying about people seeing 1. my panties and 2. my THIGHS. I use all caps because that’s how I feel about them. I’m a robust little Asian!


  • Ira

    “Canadian tuxedo”

    I have awful luck with lights. the cheap ones last a season, the nice ones are in the triple digits. I really want one that looks clean and won’t break or be stolen- they don’t seem to exist.

  • sara

    Never heard of earbags either… Just purchased Bern helmets with the winter inserts (fuzzy & warm ear coverings) for all my fellas. My boys complained a ton about cold ears riding in the cargo bike & so we were layering them with hoodies, with the hoods up & under their helmets. I figured the investment in the Bern winter helmets is an investment in us being able to continue bike commuting through the fall & into the winter.

  • Sox

    We’re finally enjoying summer here, and tho’ fall is my favourite time of year, I can wait for a few more weeks for it to arrive.
    You have piqued my curiosity by twice mentioning your Russian boots. Do you have a picture? They sound warm and I have perpetually cold feet.

  • dottie

    I wore those boots nearly every day last winter. They are the only boots I have that keep my feet warm December through February, and I wear them with two pairs of Smart Wool socks. There are pictures from previous posts here, here, and here. Not the best pictures, but they come a couple inches above my ankles, are thick black leather with thick rubber soles and have some sort of fake fur/wool lining. I’ll have to devote a whole post to them when I start talking more about winter. I bought them for about 20 USD when I was studying abroad in Russia in 2001. Never had to wear them again until I moved to Chicago :)