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

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38 thoughts on “How To: Dress for Fall Cycling

  1. cupcakerator says:

    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.

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

  3. Yvette (Slow Bike Miami wife contingent) says:

    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.

  4. Sungsu says:

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

  5. Mamavee says:

    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.

  6. miss sarah says:

    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!


  7. cratedigger66 says:

    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.

  8. Ira says:

    “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.

  9. 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 says:

      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.

  10. Sox says:

    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 says:

      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 :)

  11. Catherine says:

    “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 :)

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

    • dottie says:

      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.

  13. superbk says:

    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!

  14. E A says:

    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!

  15. Doohickie says:

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

    Well said.

  16. Scott says:

    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!

  17. Lara says:

    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…

  18. […] best weather for bicycle commuting or recreation. This post from Let’s Go Ride a Bike about dressing for fall cycling is little different than most because it’s from a woman’s […]

  19. […] this morning in Chicago was 48 degrees, with a high of 57. A perfect day to put in action my How to Dress for Fall Cycling advice. Two weeks ago I wore this strappy summer dress alone with sandals. Today it became an […]

  20. […] this morning in Chicago was 48 degrees, with a high of 57. A perfect day to put in action my How to Dress for Fall Cycling advice. Two weeks ago I wore this strappy summer dress alone with sandals. Today it became an […]

  21. Jess says:

    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 says:

      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 says:

        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!

  22. Braxton says:

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

  23. […] An oldie but a goodie: how to dress for fall cycling. […]

  24. […] “How To: Dress for Fall Cycling” – How to Ride a Bike […]

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