"Chicago, IL" 10 - best $25 Work n' Sport Super Brawny RED BUFFALO Flannel Shirt Doesn't matter. It's timeless. Warm, but not too warm. Beefy. Hi-vis. Boxy fit (unless you like that), smaller sizes frequently out of stock, too many urban lumberjacks wearing same shirt. https://www.farmandfleet.com/products/g-27277-work-n-sport-mens-long-sleeve-super-brawny-flannel.html Clothing / Apparel Autumn, Winter Cold, Snow, Increase Visibility, Wind "Chicago, IL" 9 $55 Pearl iZumi P.R.O. AmFIB Lobster Gloves lobster gloves 2016 Warm, durable, and large coverage Expensive, bulky, and can cause sweaty hands at times  Clothing / Apparel Winter Extreme Cold, Wind, Ice, Snow, Cold "Minneapolis, MN" 9 $45 45 NRTH Greazy 45 NRTH Greazy Merino Cap 2017 Lightweight, Warm, Breathable Brim is a little flimsy, not cheap. https://45nrth.com/products/greazy Clothing / Apparel Winter, Spring, Autumn Rain, Cold, Wind "Chicago, IL" 10 - best $25 Work n Sport Super Brawny CHARCOAL BUFFALO Flannel Shirt It's timeless. Sturdy, warm, classy and understated. You can wear it without looking like a clone of the three guys in your office wearing red flannels--also more "all-season" than a red flannel. Boxy cut (but maybe you like that), and sleeves are a bit short. Hard to find in smaller sizes. Not hi-viz. https://www.farmandfleet.com/products/g-27277-work-n-sport-mens-long-sleeve-super-brawny-flannel.html Clothing / Apparel Spring, Winter, Autumn Wind, Cold, Snow "Minneapolis, MN" 8 $35 Swrve Soft-shell Belgian Cap Belgian Wool Cap 2015 Lightweight, Super Warm, fits nicely over lightweight balaclava, Not too expensive Really only for deep cold, waaaay too sweaty if it's above like 20º https://swrve.us/collections/caps/products/softshell-belgian-cap Clothing / Apparel Winter Extreme Cold, Snow, Ice "Chicago, IL" 9 $50 Bar Mitts Bar Mitts 2010 Easy to put on/take off. Blocks wind. Durable. Makes it difficult to access accessories on handlebars (mirror, bell etc.) http://barmitts.com/ Bike Gear / Modification Winter Extreme Cold, Cold, Snow "NYC, NY" $8 32 Degrees Heat tshirt long sleeve  Long sleeve t-shirt Costco "Synthetic fabric does not trap sweat or moisture, so it keeps me warm and dry. Very light, thin, and stretchy, so I can wear it easily under anything, even a tight summer cycling Jersey, and cuffs do not interfere with any glove or mitten. Provides some SPF protection for arms in the event of daytime riding." Not suitable for machine drying on heat so laundry cycle should include space and time for air drying. https://www.costco.com/32-Degrees-Men's-Heat-Tee%2c-2-pack.product.100507954.html Clothing / Apparel Winter Cold "Chicago, IL" 10 - best $100 Cotopaxi Pacaya Cotopaxi Pacaya Insulated Jacket 2018 "Amazingly warm for a light weight jacket. Packs into its own chest pocket which makes it easy to throw in bike bag for weird Chicago might be 60F might be 30F kinda Fall days. Good craftsmanship and materials." The price point is a bit daunting BUT they hire refugees and the quality is top notch. https://www.cotopaxi.com/products/pacaya-insulated-jacket-men-sale?variant=28534193291325 Clothing / Apparel Autumn, Spring Cold "Chicago, IL" 9 Continental or Suomi  Snow Tires You won’t slip on black ice Some wheel resistance will make your legs stronger for next spring. Bike Gear / Modification Winter Extreme Cold, Ice "Chicago, IL" 8 $65 Keds Scout Shoes 2018 Waterproof, they're not bulky so they don't create a conflict with pedal cages like most waterproof shoes, look like normal shoes so I can wear them to any destination and don't have to carry extra shoes for work Developed a hole on the sole/upper seam after about a year (but to be fair, I wore them almost daily and abused them on my bike), had to be broken in a bit before they were really comfortable, if being used solely for winter they're not super warm but socks can fix that. https://www.keds.com/en/keds-keds-she-scout/ Clothing / Apparel Winter, Spring, Summer, Autumn Rain, Snow "Chicago, IL" 10 - best $120 Portland Design Works (PDW) Full Metal Fenders (personally, I like the matte dark brown finish) Fenders 2017 "-Never cracks or breaks  -Handles public transit (buses, Metra, CTA el) with all its bumps and squishing with aplomb -Fenders are ESSENTIAL gear for winter biking. They protect your clothing and gear, help to minimize salt spray, and they take away the worry about hitting puddles, avoidance of which might send you into traffic." -It might rattle. You can cut a chunk off a wine cork and fit it between the frame mount and the fender to avoid this, if it occurs. https://ridepdw.com/collections/fenders Bike Gear / Modification Winter, Autumn, Spring, Summer Rain "Chicago, IL" 10 - best $180-ish? I got them on sale at REI Korkers Verglas Ridge Boots 2018 "1. Warm 2. No seriously, they're warm 3. Your toes will think they're in the tropics when it's -10 out. With proper socks and these boots, my toes have never gone below chilly on a bike ride(~5 miles each way every workday, regardless of temp or windchill). I can't say enough good things about them. I even walked a mile each way to/from the gym in the polar vortex (-20s air temp, -50s windchill) in them and my feet were slightly cool but perfectly safe. " "1. Heavy (like 1.5 pounds each, I think - they noticeably weigh my feet down) 2. Bit of a pain to get on/off 3. The laces are pretty flimsy and the outer layer started stripping off pretty fast. For my second winter of wearing them, I'm going to need new laces.  They're pricey, but I don't count that as a con because compared to the cost of frostbite they're a real bargain. " https://korkers.com/collections/outdoor/products/womens-verglas-ridge?variant=24522035986532 Clothing / Apparel Winter Extreme Cold, Snow, Ice, Cold, Wind "Chicago, IL" 8 $25 I have Bar Mitts because they're cheap on Amazon. Nice ones would probably be even better. I have the flat bar ones, but I doubt there's a difference between them and the drop bar style other than the fit Pogies 2017 "1. Keeps my fingers toasty 2. As good as an extra layer of gloves, without the bulkiness 3. You can put hothands in them for extra toastiness. " "1. Annoying to get on/off the bike. 2. Can be difficult to get a double-gloved hand through the pogie opening and grip the handlebar comfortably - there just isn't enough space, and I have small hands.  3. Difficult to extract hands quickly - makes for nerve-wracking moments going over ice because if you fall your hands are trapped. https://www.amazon.com/Bar-Mitts-Mountain-Commuter-Handlebar/dp/B009F9ZQH4/ref=sr_1_2?dchild=1&keywords=pogies&psc=1&qid=1571196463&sr=8-2 Bike Gear / Modification Winter Wind, Cold, Extreme Cold "Minneapolis, MN" 9 $10-25 HeatTech and HeatTech Extra Warm long and short sleeve t-shirts, tights.  Uniqlo HeatTech 2016-2019 Cheap compared to other base layers, lightweight (fits under other clothes and can be layered for more/less warmth), moisture-wicking stays dry after activity. https://www.uniqlo.com/us/en/men/heattech-collection Clothing / Apparel Winter, Autumn Cold, Extreme Cold "Chicago, IL" 8 $8 3M Virtua CCS Protective Eyewear Foam Gasket, Anti Fog Lens, Clear Clear Glasses 2016 Foam gaskets help keep heavier rain and cold wind out of your eyes where regular sunglasses fail. Lenses are clear and thus ideal for riding at night. Comparable to wearing regular sunglasses w/ option to remove foam gaskets.  Anti-fog coating doesn't really work. Lenses scratch easily. https://www.amazon.com/3M-Virtua-Protective-Eyewear-11872-00000-20/dp/B00AEXKR4C/ref=pd_bxgy_328_img_2/142-7353305-8630752?_encoding=UTF8&pd_rd_i=B00AEXKR4C&pd_rd_r=34b40d68-6bb2-42d6-b06d-49ccc4cb3f86&pd_rd_w=mIIvH&pd_rd_wg=jwwQi&pf_rd_p=09627863-9889-4290-b90a-5e9f86682449&pf_rd_r=5X7VWGA9K8YXDYE6V5TW&psc=1&refRID=5X7VWGA9K8YXDYE6V5TW Clothing / Apparel Winter, Autumn, Spring Rain, Cold, Wind "Chicago, IL" 9 $50 Bar Mitts  Bar Mitts Cold Weather Mountain/Commuter Bike Neoprene Handlebar Mittens Amazon "These keep your hands warm when outdoor temperatures drop. They do not inhibit the operation of your bike. They're easy to install and remove when the weather changes." "These can make it a little harder to get to your signalling bell, etc. They're a little expensive for what they are. They can look a little silly, though if you're bike commuting in the winter this is the least of your concerns!" https://smile.amazon.com/gp/product/B002VK1MC2 Clothing / Apparel Winter Cold "Milwaukee, WI" 10 - best $$$ wooooooool  is warm for your cold parts, stays that way even when wet cheap wool is itchy, oh no Clothing Apparel Winter, Autumn, Spring Cold, Extreme Cold "Chicago, IL" 10 - best $17 Blitzu has always been good to me  Blitzu Cyborg 168T Lights!! 2017 "Lasts pretty much forever on one charge Waterproof effectively Bright as heck!!" "It loses its direction sometimes due to the mount Sometimes hard to get the port open Cant think of a third!" https://www.amazon.com/Rechargeable-Intensity-Accessories-Helmets-Flashlight/dp/B015IEJ0GC/ref=sr_1_5?dchild=1&keywords=blitzu+light&psc=1&qid=1572322811&sr=8-5 Bike Gear / Modification Winter Other, Increase Visibility "Nashville, TN" 9 Maybe $10 at Target on clearance? none in particular none in particular glommets 2010s Top part folds over fingers to retain warmth; can flip over if hands get too warm Can be a little bulky for shifting with integrated shifters; not always windproof depending on the brand  Clothing / Apparel Winter Extreme Cold, Wind "Nashville, TN" 9 $120 Columbia WOMEN'S SNOWPOW TALL OMNI-HEAT BOOT (don't think they are made anymore) insulated rain boots 2017 Windproof, waterproof, stretches over my calves! Can get slightly too hot https://www.columbia.com/womens-snowpow-tall-omni-heat-1701371.html Clothing / Apparel Winter Extreme Cold, Rain, Wind, Cold, Ice, Snow "Nashville, TN" 10 - best $25 Buff merino wool neck gaiter 2012 Can pull up over ears & nose for extra warmth; wool stays warm when wet; also comes in a WINDPROOF version for super cold days Not great for rain or precip days https://buffusa.com/buff-products/multifunctional-headwear/lightweight-merino-wool/denim-multi/117819.788 Clothing / Apparel Autumn, Spring, Winter Cold, Extreme Cold, Wind "NYC, NY" 9 $30 Buff Lightweight Merino Wool Wool neck buff 2013 "- Plugs a gap in coat /sweater collar - Can use as facemask by wedging under helmet/cap, and can double over to increase thickness - Doesn't stink ever" - When used as a facemask in super-cold temps, can sometimes frost over by nostrils/mouth, making breathing somewhat trickier. But everything used this way does. https://buffusa.com/buff-products/men/multifunctional-headwear/lightweight-merino-wool/castlerock-grey-multi/117819.929 Clothing / Apparel Autumn, Spring, Winter Extreme Cold, Cold "Chicago, IL" 10 - best This one is no longer made; similar models are around $200. Product link is to similar models. Columbia The one I have isn't made any longer. :( 2-layer jacket 2018 "1. It has a puffer underneath and a windbreaker over top, and you can separate them so it's very easy to adapt the jacket to different temps/wind conditions.  2. WARM. If I put a merino wool baselayer under it, I'm comfy down to about 15 degrees. With a baselayer and a long-sleeved T-shirt, down to about 0. Below 0 needs a hoodie under the puffer under the windbreaker layer. 3. Lots of pockets for all my random stuff (work keycard, keys, wallet, phone, headphones, receipts, spare Buff, chapstick, etc. etc.)" "1. Zippers have small tabs that are hard to work with bulky gloves on. Thinking of attaching big dorky pieces of plastic or something to it so I can get a decent grip. 2. There are so many zippers and toggles and snaps and random features that the jacket has a bit of a learning curve, at least if you're slow on the uptake like me. :)  3. Not very visible and no place on the back to attach a light to my body. I wish they'd make them in high-viz reflective yellow; I don't care how stupid it would look. " https://www.columbia.com/womens-3-in-1-jacket-shells/ Clothing / Apparel Winter Extreme Cold, Cold, Rain, Wind "Chicago, IL" $40-100 Continental GrandPrix 4Season Tires Tires 2019 Stopped into a local Chicago bike shop for winter tire recommendations for commuting. They said to essentially stick with what you're comfortable with - if you ride with slicks or knobby tires, you're likely going to want to stick with what you know.  Across the board though they said their shop recommends Continental GrandPrix 4Season tires. Glass is a bit of an issue On Chicago streets and these are supposed to be good for their puncture protection. https://www.continental-tires.com/bicycle/tires/race-tires/grand-prix-4-season Bike Gear / Modification Winter, Spring, Summer, Autumn Snow, Rain "Washington, DC", "Arlington, VA" 10 - best $10 Nite Ize Spokelit - Red Spoke lights several years ago For side views, makes me far more visible to cars. Easy to install.  Batteries last me all winter season/night riding. https://www.amazon.com/Nite-Ize-Spokelit-Bicycle-Spoke/dp/B07VDM5C6X/ref=pd_sbs_468_t_0/141-2986416-8741334?_encoding=UTF8&pd_rd_i=B07VDM5C6X&pd_rd_r=4af438dd-b786-44f4-92aa-ce02c652a4ca&pd_rd_w=NOcmx&pd_rd_wg=Z2pEs&pf_rd_p=5cfcfe89-300f-47d2-b1ad-a4e27203a02a&pf_rd_r=AHH5S4Y0CA6TBJF6TYJK&refRID=AHH5S4Y0CA6TBJF6TYJK Bike Gear / Modification Winter, Spring, Summer, Autumn Increase Visibility "Washington, DC", "Arlington, VA" 10 - best $90 Light In Motion Urban 1000 Ridgetop Rechargeable bike light Handle Bar light REI Exceptionally bright illumination of path ahead. Variable settings (high, low, flash). Swivels to sweep left/right as needed.  Battery drains quickly when using in brightest setting (I charge every day at work before riding home in dark) https://www.amazon.com/Light-Motion-Ridgetop-Headlight-856-0688/dp/B07C1P3JBP/ref=sr_1_9?dchild=1&gclid=CjwKCAiAh5_uBRA5EiwASW3IaifCZZt7AcsUW8MJmC6GrXSgnT-skov_mtlP_hRgvHhuYiVQGpHDxBoCeRIQAvD_BwE&hvadid=178112915184&hvdev=c&hvlocphy=9008168&hvnetw=g&hvpos=1t2&hvqmt=b&hvrand=17498287888592746963&hvtargid=kwd-2462278121&hydadcr=13935_9753344&keywords=light+in+motion+bike+lights&qid=1573420464&sr=8-9 Bike Gear / Modification Winter Increase Visibility "Chicago, IL" 9 $10 Bobster Bugeye Goggles Amber lens for days with sun, clear for days without. Motorcycle Goggles 2017 I cannot stand wind on my eyeballs. The motorcycle goggles fit better under my bike helmet than sunglasses or ski goggles. Portable, compact, haven'e scratched or crushed in my bag yet. Nothing really. I don't have problems with them fogging or being too tight. https://smile.amazon.com/gp/product/B002P3LLR6/ref=ppx_yo_dt_b_search_asin_image?ie=UTF8&th=1 Clothing / Apparel Winter Wind, Snow, Cold, Rain "Chicago, IL" 9 $20 Buff Any  Multifunctional Headwear (Headband, Balaclava) - Buff 2017 "1. Extremely versatile - can be used as a headband to cover ears, neck cover, or pulled up high over the face. 2.  Is seamless and comfortable 3. Comes in fun colors " "The ""Original"" model isn't always warm enough for super cold temperatures, so you end up needing a couple different versions for a variety of temperatures. https://buffusa.com/shop-buff/men/multifunctional-headwear-category/original-family.html Clothing / Apparel Autumn, Winter Cold, Wind "Lansing, MI" 9 $75 Bar Mitts  Bar Mitts 2019 "Easy to install Easy to use Actually works" "Aesthetics are poor Limited hand position  Looks kind of cheap" http://barmitts.com/ Bike Gear / Modification Winter Cold "Chicago, IL" 8 $35 Coldl Avenger  Cold Avenger Face Mask 2017 "Helps keep goggles from fogging Warm face Front chamber warms the air you are breathing a bit" "Like all face coverings, gets a bit wet with condensation after a while. The pro of a snug face warmer is also a  con when you have a runny nose or need to spit." https://coldavenger.com/products/classic-fleece-face-mask? Clothing / Apparel Winter Cold, Extreme Cold "Chicago, IL" 8 $300 Lake MXZ303 Boots 2017 Keep feet warm and dry. flexible and comfortable sometimes they feel loose. When it gets below 10 degrees my feet are still cold.  https://lakecycling.com/ Clothing / Apparel Winter, Spring Cold, Snow, Wind "Look for one that fits your body, water resistant is best. Add a couple of wool knit caps to your bag to give out to cold peeps. 🙏" Backpack pannier https://www.cyclingabout.com/list-of-convertible-backpack-panniers-that-can-be-strapped-to-your-back-or-bike/ Bike Gear / Modification   "Los Angeles, CA" 8 $200 Marmot E30710 Gortex shell 2013 water resistant, breathable, hood fits over your bike helmet and guaranteed for Iife. expensive, cold when really windy,  long rain session-water will get through https://www.backcountry.com/marmot-minimalist-jacket-mens?CMP_SKU=MAR01JP&MER=0406&skid=MAR01JP-SUR-M&mr:trackingCode=F8623001-5824-E911-810A-005056944E17&mr:referralID=NA&mr:device=c&mr:adType=pa&mr:ad=8823334175&mr:filter=4580428007686531&iv_=__iv_c_8823334175_w_pla-4580428007686531_g_3780426148_n_o_e__h__ii__j_4580428007686531_z_US_f_Online_o_MAR01JP-SUR-M_i_EN_s_Backcountry.com_q_marmot%20gore%20tex%20rain%20jacket_p_2_d_c_vi__&CMP_ID=PLA_BNmyDeviceIndicator=c001&utm_source=Bing&utm_medium=PLA&k_clickid=1f2da81d-06dc-4283-a29d-ecfe4baf39f3&msclkid=9044bd6254591be12dcfe0abcde9eba2 Clothing / Apparel Autumn, Winter Cold "Chicago, IL" 8 $75 PEARL iZUMi P.R.O. AmFIB Lobster Glove Lobster Gloves 2018 Keeps hands warm and dry even in very wet rain/snow mix. Slim enough to provide good dexterity and not cause accidental shifting (which my heavier gloves tend to do). Warm fingers down to just below freezing. Reflective bits on the back are a nice feature. Not for extreme cold - around about 20deg they start to be not warm enough for me. Sizing is all men's so is odd for my average (female) hands - the XS is too long for my fingers (I'm talking almost a full inch of space that can fold over at the tips of the fingers) but too narrow to fit over a sleeve/jacket cuff or fit comfortably over liner gloves for colder weather without a struggle and loss in dexterity. https://www.pearlizumi.com/US/en/shop/unisex/gloves/road/pro_amfib_lobster_glove/p/14341508 Clothing / Apparel Winter Snow, Cold "Austin, TX" 10 - best $250 Showers Pass elite 2.1 jacket elite 2.1  Jacket 2010 Waterproof, warm, light, yellow cost https://www.showerspass.com/collections/mens-waterproof-jackets/products/mens-elite-2-1-jacket Clothing / Apparel Winter Rain, Cold, Wind Chicago 9 $25-$35 Simms, NRS, house brands- look for fishing and kayaking gear companies Depends on thickness and level of extra protection needed Neoprene wading socks 2012 Warm, wind blocking, water resistant/ proof depending on model.  Sometimes too hot and can cause feet to sweat. https://www.rei.com/product/114954/nrs-hydroskin-05-wet-socks Clothing / Apparel Winter Rain, Extreme Cold, Wind, Cold, Snow