cycle guy
Only you can answer this for sure. I ride with my kids maybe 10 or 12 miles and will wear regular shorts. But I ride 100+ miles a week and use cycling shorts for most all of the miles. If you have a current problem with chaffing etc. try 'em thay are the best for cycling for sure. For a 5 mile ride I likely wouldn't bother, but I ride 20 to 40 miles per ride and for that I do. i always wear gloves, helmet and cycling shoes - unless I'm tooling around the 'hood.

Maestro1999
Definitely worth it, but look around. They will make riding your bike more enjoyable and comfortable. Don't buy the first pair you find, and don't go cheap either. I would reccomend getting two pairs, so you can alternate and have always have a clean pair ready. you can also get baggier style ones that still have the padded liner in it. Check it out I wear this brand and love them.

jonathan.javorsky
it should the second thing you get. and be willing to spend $45 and up. the more you spend most the time the better they are.

intrepidfae
Padded cycling shorts make a big difference. It's not only the padding, it's also the flat stitching to avoid chafing and the moisture wicking material to keep you as dry as possible. Don't wear anything under cycling shorts -- "go commando." Underwear defeats the purpose of cycling shorts. I buy my shorts from Performance when they are on sale. I've owned the Century Gel and Ultra models. They are both good. HTH

joan t
I've only been wearing regular shorts so far, but I think biker shorts are very attractive and comfortible, prevent fatigue, and hold muscles in place while cycling. All of which are good reasons to invest in some biker shorts.

Carpetony
I would concur with CycleGuy and am surprised someone knocked him for his answer. I'm about the same, if the time I spend getting ready exceeds the length of the ride 'figuratively' I forego the cycling shorts. If you're uncomfortable in straight cycling shorts, black spandex per se, you can always wear a casual short over them, or get mountain bike shorts with cycling short built in - akin to men's swim trunks with built in liner. I like my Borah Mountain shorts when I get out on the trail or ride my cyclo-cross bike around. I found this page with some examples of both types of shorts. And just like shoes different manufacturers fit differently. Get out and ride!

M R
Probably. Like cycle guy and carpeton... said it's up to you. Good point about getting ready time. The more riding you do the more they will help. Like some others said, on short rides I don't waste time going full kit. I ride with my young daughters too, many times helmet, gloves and glasses is all I use. I just ride my clipless pedals with sneakers - it's no big deal for a 10 mile easy ride. You can get padded shorts for <$30 on sale, so buy a pair and see how you like them. If you will be riding almost daily and doing longer rides on the weekends, I'd buy a pair if I were you.

k
YES i really like pearl izumi they make the ride much more enjoyable and less painful check out chainlove.com they sometimes have womens shorts up also longcycles has some good deals as well as places like rei, sierra trading post, and backcountry