Fashion, Music, What to wear to...

Music Festival Outfits For Men Sure to Boost Your Lollapalooza Look

lollapalooza outfits guys

This article was written by The Zillennial Zine’s summer editorial intern PJ Cunningham. Find him on Instagram at @peachycunningham. If you would like to share an article with The Zillennial, send us an email at

It’s almost that time of year again. The heat of the July sun almost mirrors and exemplifies the anticipation that the hundreds of thousands that venture annually to one of the nation’s largest music festivals feel. 

I am of course talking about Lollapalooza, Chicago’s famous four-day music celebration that features some of the world’s largest artists and will feature 170 performances this year. As a born-and-raised Chicagoan and fan of music festivals, I am looking forward to attending this year’s edition.

However, there’s more to be excited about than just music. If you’re anything like me, picking outfits for Lolla is one of the most exciting parts of the entire weekend. There are, after all, few better places for one’s self to express creativity in fashion than a music festival.

That being said, it can be incredibly difficult to decide what outfits to wear to Lollapalooza, especially for guys. From dressing for the July heat to making sure you fit the vibe of the festival to making sure you’re comfortable but stylish, it can be a daunting task trying to pick the perfect outfit for a music festival.

Luckily for you, we are here to help. Listen up my brothers, here are some surefire ways to level-up your Lollapalooza looks while also staying comfortable.


The Jersey

Creative, rare jerseys may not always come cheap (though there are plenty that pop up at almost any local thrift store), but they can be incredibly fun. I love my 90’s Charlotte Hornets Muggsy Bogues jersey (he was the shortest NBA player ever, by the way), not only because of its unique coloring and retro appeal, but also because it features a special and relatively obscure player. However, if you are a fan of big name teams and players, those are also always fair game. After all, icons always inspire. Examples of this include two of my soccer jerseys below, featuring well-known French club Paris Saint-Germain (left) and Mexico-city based Club America (right). While these are not exactly collectors items, their color and brand name presence make them music fest mainstays.

Lastly, the joke jersey or TV/film reference jersey is always fun. Not only will it receive positive attention, but it will also likely be among the rarer finds in the masses gathered at Lolla. One such example is my jersey from Will Ferrell’s hit basketball-spoof movie Semi-Pro (2008), which features the name of main character Jackie Moon.

While they’re hardly fine-fashion, the jersey, whether it be pieces similar to those I provided or those from other sports like football, hockey, or baseball, is a music festival mainstay for men across the nation for good reason. Not only are they fun, but more importantly, they’re also generally breathable and comfortable. Trust me, if you want to enjoy Lollapalooza, that is essential.

The Breathable Button Down: Classy, Cool and Comfy

Button-down shirts are a no-brainer for those who want a more refined look at Lolla, while still staying cool and comfortable in that early August heat.

Linen shirts, such as those above, combine class and comfort seamlessly. Linens are especially breathable, a must-have attribute of any summer festival clothing, but can still look clean and fitting.

Be warned however, wearing white linen is Lollapalooza lunacy! While they always look good, white linens, or any white articles of clothing for that matter, will almost surely get dirty and perhaps even stained from the potential dust, drink and food spills and yes, even sweat (yuck, wear deodorant people!) that unfortunately accompanies a major outdoor concert.

Visual and Versatile: The Go-To Graphic Tee

If neither of these options are your thing, I cannot suggest the graphic t-shirt enough. I especially urge you to look for slightly larger, baggier graphic tees, as those are not only in style, but also provide the aforementioned much-needed breathability essential to Lolla survival in the mean Chi-town humidity.

Furthermore, graphic tees allow for a ton of potential modes of expression, as there are shirts for nearly every pop-culture entity out there, alongside brands, musicians and bands and even foods. If you want to show your colors, a graphic tee is your go-to!

With many thrift stores as well as major retailers selling graphic tees, they should be very easy to find. However, for the more digitally inclined, websites such as Ravers Warehouse and Design by Humäns provide many music festival-centric graphic tee options.


Short(s) and Sweet

The section on bottoms will be a lot shorter. This is for one simple reason, heat!

Okay, Lollapalooza really isn’t the Sahara desert, I swear. In fact, the breezes of Lake Michigan can be quite refreshing. This is, after all, the Windy City. However, shorts provide both comfort and increased mobility, two major pluses for music festival attire.

I recommend light-fabric shorts that go well with the color of your top and are comfortable. While not everyone loves the trend of shorter shorts, such as 5’’ inseam shorts, I for one think it’s great. Shorter shorts aren’t just comfy, but they also look great.

If you are sold on wearing pants without a shadow of a doubt, I recommend baggier pants.

If you guessed what I’m gonna say next, kudos to you.


Sure, I know that if I took a shot every time I wrote the word ‘breathable,’ in this piece, I’d not be in any state to go to a music festival, but my reinforcement of the point is essential.

It will be a somewhat hot day, but the elements don’t have to be a hindrance if you don’t let them be. Baggy and light pants, though just one aspect of an outfit, can be both fun and relaxing.

Shoes: Keep it safe, Keep it simple

No matter what you like in a pair of shoes, foot and leg health should always be paramount. This is true for Lollapalooza too. While everyone wants to look their best in their finest kicks, one must remember that outdoor music festivals aren’t known for their cleanliness nor their comfortability.

Between dirt and tired feet, it’s likely best you bring a pair of shoes that are comfortable and supportive, while also stylish. For ideas on shoes for Lolla and other music festivals, visit the OnePointFresh website and begin browsing!


Accessorizing one’s outfit might not sound like a traditional men’s practice, but it should be and will be for our purposes. No Lolla weekend is a proper experience without the swag that can only come through personalized expression through outfit accessories.

Whether it be the once-lambasted now-heralded fanny pack or the classic bandana, accessorizing one’s outfit, within reason of course, is a fool-proof way for any guy to up his Lollapalooza style game.

GIF by Lollapalooza - Find & Share on GIPHY

So, now that we have covered our main bases, it’s time to begin choosing which outfits, from jerseys to Jordans, that one will bring to Lolla. While it might sound difficult to do the festival justice with your outfit, the truth is that some of the best outfits come not from aesthetic boards or store sales, but rather really for the individual who wears them.

At the end of the day, making a perfect Lolla fit must come from within. Otherwise, that would simply disregard the most important aspect behind this whole story, the need for self-expression.

So, get the playlist going, open up your closet and get ready to love this year’s Lolla and level up in style!

Do you have any other ideas for lollapalooza outfits guys would love? Let us know in the comments!

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