The search for the perfect relaxed fit shirt seems to be something that still occupies the minds of anyone interested in fashion. Whether you feel that more relaxed fit shirts are on the way out or they are still a force in the zeitgeist, I believe everyone needs a good relaxed fitting shirt that you can wear with just about anything. My obsessiveness with clothing and they way I like my clothes to fit me has helped me find a handful of really great shirts from some amazing brands that fall into this category.
With it being the height of spring right now and summer just around the corner, I wanted to talk about and recommend seven of my favorite relaxed fit shirts and where you can purchase them right now. I’m also going to give my opinions on sizing advice to help out, which you should take with a grain of salt because everyone likes their clothing to fit a certain way. I know that I love to see how items fit from someone who actually owns them rather than just looking at sizing charts, especially when it comes to t-shirts. Each of these are shirts that I actually own and have worn a lot. There are some cheaper and more expensive options on this list as well so I hope there’s something for everyone here.
18 East Grahame Big Tee
This tee from 18East is probably my favorite relaxed fit shirt that I own. It’s a great heavyweight cotton fabric that feels surprisingly breathable. I absolutely love the wide flowing fit and dropped shoulders. These shirts are also handmade in India. I got my normal shirt size and I love the way it fits. You could probably go one size down and it would still be very relaxed fitting. It lives up to its name as a very big shirt but in the most perfect way. I don’t have much more to say honestly, this might be the perfect relaxed fit shirt out there.
Bare Knuckles Basics T-Shirt
I love the wash look of these shirts from Bare Knuckles. They also come in all the colors of the rainbow quite literally. This shirt has the perfect crop without it being too short or too trendy that it will go out of style. The fabric has a great hand feel and one my favorite details is the sewn on, bound neck collar. The collar on this shirt keeps its shape no matter how many times you wash it. I went true to size on this shirt as well and the fit is excellent. I will say if you are on the taller side or well built, you might want to go one size up if you want a nice oversized fit as they do shrink a bit after the first wash. Made in Los Angeles, this shirt will be one you reach for time and time again if its in your closet.
Stussy Pigment Dyed Tees


I love Stussy’s graphic tees, I have way too many in my drawers. I think Stussy has some of the best wardrobe basics on the market, especially when it comes to t-shirts. My number one recommendation with Stussy tees is to get the pigment dyed versions. The pigment dyed material just feels so much nicer than the regular cotton tees and they fade beautifully when you wash them. I also feel like all of the pigment dyed tees I own fit a little more on the relaxed side than the regular cotton tees as well. I also cut basically all of my Stussy tees so they fit a bit more cropped/boxy, I highly recommend doing that. My only gripe with Stussy tees is that they are way too long. I usually only take a couple inches off and I feel like they fit me and look much better. If you want to have them extra relaxed you could opt for a size up from your normal size and cut them or have them tailored as well. I like the raw hem on the shirt that rolls up, but if that’s not your jam then go to your friendly neighborhood tailor to get them fixed up for you (and if you don’t have a tailor, find one, you’ll thank me later).
Buck Mason Field-Spec 90s Boxy Tee
I picked up this shirt recently and I do not regret it. This is definitely a strong contender for the perfect white t-shirt. It’s not extremely relaxed or oversized or cropped, it’s balanced right in the middle. This t-shirt is also THICK, which I absolutely love. I got my normal size and I would definitely recommend going true to size. For the fabric and build quality, this shirt is at a very affordable price point as well. Buck Mason smashed it with this shirt. Everything that they design is very minimalistic yet very intentional in a great Americana way.
Carhartt K87 Loose Fit Pocket T-Shirt
This shirt is the epitome of “bang for your buck” at only $15. It comes in tons of colors, has a great heavyweight feel, and will last for years even if you beat the heck out of it. I have a few of these t-shirts and I wear them constantly. I sized up one size from my normal shirt size with these but even if you stay true to size they are still very loose fitting. This is one of those shirts that you can throw on with anything and not have to worry about it.
Our Legacy Workshop Box T-Shirt


Our Legacy is one of my favorite brands. Unfortunately these Work Shop t-shirts are sold out right now online but they are some of my favorite shirts I own. They have a nice lightweight feel without being flimsy or see through and they have a great cropped fit that finishes right at the waistline. I would recommend going true to size on these t-shirts as well.
Hidden NY Logo Tee
Hidden is another great option if you want some graphic tees. I went one size up from my normal shirt size on all of my Hidden tees and I like how they fit like that. I do shorten the length a few inches by cutting them or taking them to the tailor. Hidden usually has drops every few weeks and the webstore will stay open for a day or two, so you have to be quick if you see a design that you like.
That concludes my list of my favorite relaxed fit tees. Hopefully you found a new piece that you want to add to your wardrobe now (my apologies to your bank account). A great relaxed fit tee that you really love really is a necessity, especially during those hot summer months when it gets hard to make your outfits interesting. Catch me in the 18East big tee and Patagonia baggies all summer long.