Yard workYard work is probably one of these easiest places to get started going shirtless. It's hot and you are working, so it gives you plenty of reason for taking your shirt off. One of the concerns that guys often have when they haven't previously been accustomed to going shirtless, is that people will say something to them that they wouldn't say to someone else because it seems out of character. Why are you going shirtless now? I've never seen you shirtless before. When you are working out in the yard, especially on a hot day, you can always say, "Well, it's really hot out here. I thought it would be more comfortable." And shrug it off as something quite natural. Which it is.
Another benefit for yard work is that you are in your own yard, so you don't feel like you are invading someone else's space. It's your own yard after all, whose business is it but your's if you feel like pulling off your shirt?
RunningAnother great place to start is running. This is another place where it comes quite naturally, especially in hot weather. And you can always choose a route that makes you more comfortable running shirtless, socially. You may want to avoid routes initially that take you by a lot of people you know. Again, guys are often concerned that their friends will think it is odd because they haven't been accustomed to seeing them shirtless in the past. After you have been running shirtless for a month or two, if you happen to bump into a friend who seems surprised, now you can just casually say, "Oh, yea, I've been doing this for a while." Or, "I always run shirtless when I run this route."
Another thing to consider is choosing a route where a lot of other people run shirtless. If there is a park or track where there are a lot of people running shirtless, you may be more comfortable running shirtless there, too. You will just fit in. You may want to avoid running in areas where small children play or near store fronts. While there is nothing really wrong with it, it may make you feel awkward. Choosing a route where shirtless runners are expected will make you feel more comfortable. Rural or wooded trails are also a good choice.
Around the houseThis one can be a little tricky, especially for younger guys who still live at home with their families, but the privacy of your home can be a great way to get comfortable going shirtless. If you have older brothers who hang around the house shirtless, or your dad does, it should make it pretty easy. If not, you might try starting by going shirtless from the shower to your room, or coming in from yard work or running shirtless. Your room may also be a good place to start going shirtless. But respect your family's standards, if mom doesn't allow guys to eat at her table shirtless, don't push it.
If you live with guys (roommates), it should be easier. You have basically equal say in household matters, and it's pretty normal for guys to go around shirtless in front of other guys, so it shouldn't offend their sensibilities. If they say something, you could even make a joke about it, "What? Is this too much manliness for you to handle?"
If you are the head of your own household, that should also make it easier. You may still want to ease into it, starting with things like coming from the shower or coming in from running or yard work, but you set the standard. Don't be ashamed to be comfortable in your own skin in your own home.
Find shirtless activitiesTry finding other activities where guys are already going shirtless. Many of the sports previously mentioned on this blog are good options to try. If other guys participating are already going shirtless, it makes it a lot easier for you to do so as well.
ClimbingRock climbing or bouldering is a great choice where you will often find guys going shirtless. If climbing interests you, you could search for climbing gyms in your area and visit each of them to see if there are guys going shirtless there. You can also ask others if there is a place in the area where they go to climb outdoors. Often guys will go shirtless outdoors, even if they don't in the climbing gym. Take a few lessons, get your own shoes and gear, and hit the rocks.
Ball GamesCasual outdoor games of basketball, tennis, or sand volleyball are also good options. Frequently guys will take their shirts off when playing outdoors, and occasionally you may find guys playing basketball in a gymnasium shirtless. If these games interest you, look around for a place where you find other guys playing shirtless and join in. Often you will find this at a park or outdoor recreation facility.
CrossFitIf you are looking for a good all around workout, you might try CrossFit. Almost every CrossFit gym allows guys to train shirtless and the practice is pretty common. CrossFit emphasizes a minimalist approach, focusing on intense workouts for functional fitness, rather than gear and superfluities.
Even the kids often go shirtless at CrossFit (yep, they have a CrossFit Kids program).
Submission Wrestling and MMAIf you are inclined to sports with physical contact and aggression, or interested in learning to defend yourself, you might try submission wrestling, no-gi Brazilian Jiu-Jitsu, or MMA classes. While it is very common to train and compete in these sports shirtless, some schools require shirts to be worn in training. Visit the school or ask before you sign up.
Really get into itWhatever you do, really get into it. Don't just use it for an excuse to hang out shirtless, that's weird and you'll miss out on most of the fun and fitness benefits. It really misses the point.
Going off to collegeWhen you go off to college is a great time to start new habits, to remake yourself in a sense. Nobody has a bunch of preconceived notions about you, so even if you have always been hesitant to shed your shirt in the past, it won't seem odd or out of character for them. Plus, a guy's dorm is a great place where going shirtless is widely accepted as normal. Embrace the opportunity to make a new, more confident you.
Getting in shapeI don't want to imply here that you need to be in great shape and have a six pack to take off your shirt. In fact, I explicitly encourage guys not to worry about their imperfections, to be accepting of their own bodies and comfortable in their own skin. But getting in shape can certainly help improve your confidence and has it's own obvious benefits. In fact, encouraging fitness is one of the key benefits of going shirtless.
There are two paths to shirtless freedom and if we want to get the real benefits of it, we must balance the two of them. One aspect of this is accepting ourselves and our bodies. We don't have to like every aspect of our bodies, but we should be comfortable in our own skin. But while dwelling on our imperfections to the point of causing stress and anxiety would not be good, it is also a mistake to become so comfortable and accepting of ourselves in an unfit state that we no longer care about taking care of our bodies and bettering ourselves. Going shirtless should motivate us to care for our bodies and promote life-long fitness. Part of the shirtless experience is feeling a connection with our own bodies, it should make us aware of our bodies so that we appreciate and care for them.
So if you don't feel comfortable with the way you look shirtless, it may help to try to get in shape first. But don't feel like you have to attain perfection to shed that shirt. It is a journey and going shirtless should help encourage you along the way.
ExerciseExercise is the foremost thing you can do to improve your fitness and your physique. But it doesn't have to be complicated and you don't need a big gym with a lot of equipment to do it. Regardless of your goals, I recommend for everyone to do a combination of aerobic exercise and resistance training.
Running is one of the simplest things you can do. If you aren't fit enough to do much running, start by walking, then begin jogging sections until you can run a good stretch. If you are already reasonably fit, you can get better results in a shorter time by doing high-intensity intervals, ie- running as hard as you can (110%) for a short space (30sec-1.5min), taking a short rest, and then hitting it as hard as you can again.
For resistance training you can do calisthenics, like push-ups, pull-ups, sit-ups or crunches, and leg raises, plyometric jump squats, and other basic exercises that require little or no equipment. You can also lift make shift weights. I have known guys to do squats with a large rock found in the park, etc. If you have access to weights at home or in a gym, pick a weight you can lift eight to twelve times. You should work each muscle group two or three times a week and rest at least 48 hours before working that muscle group again. You could do one to four sets for each muscle group. Especially for beginners, doing just one set gets a lot of the benefit you will get from doing two or three sets. Each additional set provides some additional benefit, but there is a law of diminishing returns, so the additional benefit is never as great as the benefit of the previous set. Of course, if you want to be competitive in any way, additional sets are absolutely mandatory. But for basic fitness, a single set may suffice and makes for a short workout that is easy to fit into your schedule. If you do additional sets, you should rest 2-3min between sets.
Getting involved in a sport really is one of the best ways to get exercise because it makes it fun and easier to stick with when you are doing something you enjoy with other people who encourage you.