10 - best $25 Flannel Shirt Work n' Sport Super Brawny RED BUFFALO 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. 9 $45 45 NRTH Greazy Merino Cap 45 NRTH Greazy 2017 Lightweight, Warm, Breathable Brim is a little flimsy, not cheap. 10 - best $25 Flannel Shirt Work n Sport Super Brawny CHARCOAL BUFFALO 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. 10 - best $100 Cotopaxi Pacaya Insulated Jacket Cotopaxi Pacaya 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. 8 $65 Shoes Keds Scout WF58953.jpg  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. 10 - best $120 Fenders Portland Design Works (PDW) Full Metal Fenders (personally, I like the matte dark brown finish) 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. 9 $10-25 Uniqlo HeatTech HeatTech and HeatTech Extra Warm long and short sleeve t-shirts, tights. 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.8 $8 Clear Glasses 3M Virtua CCS Protective Eyewear Foam Gasket, Anti Fog Lens, Clear2016 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.  10 - best $$$ wooooooool is warm for your cold parts, stays that way even when wet cheap wool is itchy, oh no 10 - best $25 neck gaiter Buff merino wool 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 9 $30 Wool neck buff Buff Lightweight Merino Wool 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. $40-100 Tires Continental GrandPrix 4Season Tires IMG_4445.jpg (https://dl.airtable.com/.attachments/bebe46516b63f70138361ae2791dde84/d059caec/IMG_4445.jpg) 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. 10 - best $10 Spoke lights Nite Ize Spokelit - Red nite ize.jpg (https://dl.airtable.com/.attachments/913feed0947cc25145b8ed46f2458ed9/ba0c32f9/niteize.jpg) several years ago For side views, makes me far more visible to cars. Easy to install.  Batteries last me all winter season/night riding. 9 $20 Multifunctional Headwear (Headband, Balaclava) - Buff Buff Any 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. 8 $300 Boots Lake MXZ303 2017 Keep feet warm and dry. flexible and comfortable sometimes they feel loose. When it gets below 10 degrees my feet are still cold.  Backpack pannier "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. 🙏 8 $200 Gortex shell Marmot E30710 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 10 - best 30 Cap Walz Classic cotton 3-panel 2018 "Fit. Comes in 2 sizes. Style. I like the classic ones with the stripe.  The cotton is surprisingly effective in really hot and cool weather alike - this is my go to cap from 45 - 100F." "Peak doesn't have the crisp light-switch snap up. Cost. " 9 Mine was a gift, but the Specialized website has the updated version for $200+...oof. Specialized Deflect H20 Comp Jacket Specialized Deflect H20 tSuper high-viz (I refer to this color as ""Please-don't-kill-me Pink"") It has a nice little soft fabric bit at the back of the neck that helps delay water trickling down the back. For photo reference, I am about 5'4"", 135 pounds, wearing a size small. It's snug but not too tight. " "It's Specialized, so it's absurdly expensive (mine was a gift). The pockets are pretty small for a phone. "10 - best $40 on sale Merino wool shirts I like the REI brand because it's equally durable but cheaper than Smartwool. 2019 "Warm, but not bulky. Anti-stink magic Can also be worn as a casual walking-around shirt. Photo reference: I am 5'4"", 135#, wearing a size S. " Honestly nothing.  8 $60 on sale Rain pants REI Co-Op Junction2019 "Water-resistant (not waterPROOF) but breathable. Easy to move around in. Convenient lower thigh pockets to accommodate the actual movement of bicycling instead of having everything scrunched up at the hip crease. ALL PANTS SHOULD HAVE THIS. Photo reference: I am 5'4"", 135#, wearing a size Medium. They are comfortably loose on me; I might be able to squeeze into a small but I like room to move around. " Nothing, really. They're fine for what they are. If you want super insulated winter pants, these are not the pants for you. They aren't making any effort to be as thin as possible, but they're only very lightly insulated.