Adaptability is key. The old saying of dressing in Layers definitely applies. you can always wear TWO jerseys or TWO socks if you need to for example. Fit should be snug; but not binding. Remember you are moving through the wind and you do not want any "sails" to be put up.
Helmet
No one likes to mess up their hair; but it won't feel very good when you hit your head on the ground either. The helmet should fit low across your forehead. Some people like visors and some people cannot stand how they block their vision. Luckily visors can be adjusted for the most part. They help with the rain and with a strong sun. The straps should be TIGHT, to the point where you can't put more than 2 fingers beneath your chin almost to the point where you can feel it when you swallow. If it's not tight then there is no real point in wearing it as it will just move when you crash and you will still hit your head and the helmet won't do it's job. (pet peeve of mine).
I have cracked a helmet and was happy to go to the store the next day and get a new one. Because I could. I now have 3 helments, a Giro E2, Giro Zen and a new Bell Volt. Every helmet that I've bought is progressively more comfortable than the last. Having 2 helmets is nice for when you wash one or it was raining the day before.
Bicycle helmets are single impact devices, most companies have crash replacement policies and you get a discount when you bring it in.
There are many types and some fit some better than others, square heads, large heads, cone heads ... just try them all one and see how they fit. Nothing too heavy with a lot of vents is always good. I'm not a fan of black helmets, when subject your head to more heat from sunlight in the middle of August.
Eye wear
Most important when you are riding that you protect your eyes, you are going 20km per hour and an object shot up from someones tire is going at least that fast essentially doubling the speed as it impacts you eyeball. It's going to hurt and you could lose control and crash. Sunglasses are nice; but make sure they aren't too dark. In the shade it's not very effective. Trail riders, I like yellow or amber. some people like red lenses. No dark grey lenses trail riding. on the forest floor there are a lot of shadows where you won't be able to judge a rock or a log very easily. Road, I like wearing my polarized glasses; but always carry a change of lens for when i get caught at dusk getting home.
In or out? where do you put the arms of your eye wear. I put mine out, they aren't snugged up against my face and when you crash they will easily fly off your head. If they are inside the straps, when you crash they stay with you and drive into your face.
Gloves
They are for providing even grip on the bar. The palms are important because when you crash you reach out with your hands and the scrapes you get are painful. I like a sweat pad of some kind to wipe away ... sweat ... some like to use it as a snot rag too. (i.e. don't share gloves).
1/2 Finger gloves were invented for road riding; but you could use full finger or 1/2 finger gloves for either type of riding and not be laughed at. (unlike a riser bar with bar ends). The back has mesh to keep your hands cool and having a good wrist closure is important for some people. Being able to get the gloves off is also something to consider. Testing gloves requires a bar, just putting them on might not be comfortable, I search out a bike to grip to see how they really feel.
Full fingers gloves are for trail riding, they keep you from getting scrapes from thorns or branches. I like them because the finger tips are usually rubber coated and my sweaty fingers do not slip on the break levers. this is also handy for when it is raining on both road and trail rides. With a dry enough chain it's easy to just use your gloves to pull the chain back on (see my notes on wax and chain maintenance)
Shoes
Stiff soled shoes are best. For people going clipless, the stiff racing shoes are super stiff and could be uncomfortable on long rides. For trail riders, you also have hike-a-bike situations that you have to deal with. Some nice shoes are heavy; but they are comfortable to wear all day long. Mesh is good for ventilation in the summer. Road riders need only worry about the pedalling aspect, so super stiff and a nice snug fit (shifting around adds a lot of irritation). Trail riders have to think about how much they walk off their bike. Personally I use mountain shoes on my road bike since I can get off and walk plus the cost of another set of shoes and pedals turns me off. The important aspects of shoes, HEEL CUP, how your heel fits in your shoe and the heel lift when you are riding. Try it out, with your shoes on try standing on your toes and you can sense the amount that your foot comes out. Good shoes can really hold you in and some have cinches to wrap around the heel of your foot.
The insoles on the shoes are important just like on walking shoes. Thin insoles are best since the tight straps can pinch and cut off circulation. I'm a fan of the ratchet straps because they really hold on. velcro is ok; but if you get into a bog your foot will come out of the shoe and you might lose your shoe. ratchet straps are solid nylon (or metal) and can hold you in. Lace up shoes are good with a cover over them in the colder periods, the shoes from Lake for instance are really comfortable. I ride Sidi Dominator 5's because Sidi's come in 0.5 sizes (i.e. 45.5EUR)
If a 3/4 length shoe or hi-top came out I think I would get one; but some people don't like the ankle restrictions.
Shorts
No underwear or use specialized cycling underwear, these have no seams that will chafe and ruin your day. I like Peal Izumi shorts; but the idea here is just enough padding but non-bunching chamois. The idea is not to provide padding; but to reduce chaffing. The big difference in shorts is the chamois and the panel count, the more panels the more contoured the shape of the short. Sure there are some really cheap shorts out there that are made with lower quality lycra and if you are ok with the feel then all the power too you.
For super long rides, like the second day of the MS-Bike Tour, you can put on a second pair of shorts to give you additional comfort.
Chamois Cream, it has 2 purposes. 1. to help reduce chaffing 2. to add a little anti-bacterial cream to eliminate the possibility of a saddle sore. These Saddle Sores are the result of clogged pores from wearing shorts for hours on end.
DEET, the bug spray is BAD news for lycra, it dissolves the material so avoid it at all costs on your biking clothes.
Bib shorts? These shorts cost more but have built in suspenders. They are nice if you find that your shorts fall down or if you find the elastic drawstring irritates you (as it does me). I like bib shorts a lot; but they cost a lot more.
Try not to wear your shorts when you do not need to. When you are finished riding get out of them as soon as you can.
for more casual riding I have recently invested in baggy shorts, just so I can lounge around the park and not feel awkward. Some have a good liner too them. But this is just 2 pairs of shorts in one so they are heavier.
Jersey
I like a loose fit; but it's got to have at least one pocket in it. The race jerseys are too tight in the arms for me with their elastic cuffs. I like Raglan jerseys but they don't tend to come with the 3 back pockets. In these pockets you can carry your racing chit (24hrs racer heed this), spare food or tools and at night time the battery for you light source (again 24hr racers take note). A long front zipper is good to properly ventilate. Pro's wear a thin undershirt under their jerseys, it helps to transfer the moisture off of them (I only try this on temperate days, spring and fall)
I'm experimenting with using a base layer throughout the summer season. Reportedly to help keep you cooler by giving an extra layer for the moisture to pass back through to the jersey. I'll let you know how this works out for me; but from what I've read it's the way to go and besides, all the Pro's do it!
Vest
Next to your basic kit described above, a vest can save you. windproof in the front and vented in the back on a chilly morning it can really help and can be opened up to let air through or closed up around your neck to keep the heat in.
Arm & Leg warmers
Great add-ons that you can put on during a chilly morning or late evening and can take off and put into your back jersey pockets when you are warmed up.
Socks
I do not know of anyone that wears padded socks. Usually thin, ankle socks do the trick. Merino socks are great as they don't stink and they help keep your feet dry on all but the HOTTEST of days. Otherwise socks like the Pearl Izumi Attack Sock are just fine. I also use Velotique Ped socks, they are low cut so you don't get ankle tan, they are cheap and they are thin. They work great.
What About Cotton??
I do not know of any case wear you would want to do any type of sport in cotton, it gets you cold, it stretches and it stinks. I am a fan of Merino wool and on cool days a thin merino shirt and merino socks will help you a lot. So go with synthetic dry-fit type or wool.
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