Categories: Men's Fashion

8 Lollapalooza Outfits For Guys You’ll Want

Inside a sometimes not-so-forgiving city’s Grant Park, people come from around the world to stop work and just listen. This August, thousands will flock to Chicago to listen to music and enjoy it with the people around them. This is a nearly perfect opportunity for us guys to show some confidence and jump into an outfit that will make us feel uncomfortable. No matter what you choose to wear, we hope you enjoy the unique atmosphere that is Lollapalooza. Here are 8 outfits for guys that you’ll want.

1. The Bandana

The bandana is perfect for someone unsure about wearing an outfit that will push themselves out of their comfort zone. Make just the slightest of efforts, and pat yourself on the back for wearing a bandana when you walking through the digital turnstiles to Grant Park.

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2. The Classy Tank

Having done the muscle look with a cut-off or two (or six), I prefer the classy tank look as a more mature, put together, and inviting tank top outfit. Find this tank here, and look for other classy tank designs on

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3. Linen Shirt: Short Or Long

There will not be a lot of dudes wearing linen shirts, short or long, to Lolla this year because no one says linen shirt when they think music festival. It’s more appropriate than you may think. The linen shirt is perfect for the guy that wants to look more mature, but still stay on the fashionable side of things by wearing clothes that will fit him well, and are unexpected. With a thin texture that will help you breathe and the panache of a formal shirt without the collar we are used to, you have yourself a unique look, my friend.

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4. Blackout

Does black look good on you? Go against the grain and wear all black. Put this outfit together with H&M sleeveless tee and cropped black jeans for under $30, and you have a statement outfit that does not take a lot of thinking power. If you have any neck jewelry, it looks great to add a subtle interruption to the black that is your outfit.

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5. Bum Bag

The bum bag is a confidence piece. We know men can rock them just as well as women can. Let’s show ’em. The bum bag is smaller than the fanny pack, and will be much more manageable in a crowd of people. There are several bum bags online for cheap, but none without a brand name or logo on the front. Keep those valuables close to your chest with ApeNBird‘s waterproof and logo-free bum bags or fanny packs.

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See Also

6. The Vertical Striped Tee

The vertical striped shirt is trending hard. Lollapalooza outfits will be saturated with vertical striped button downs, so I chose a clean TopMan top with enough white that it will shine in the sun. I’d finish this look off with an unexpected pair of dress shorts. Pick whatever you want, as long as the colors are loud. Go with all white, pink or the one with pineapples on them. It fits the Lolla vibe, and that’s why we’re here in the first place.

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7. Rock Out With Your Romper Out

Show off your buns ‘n thighs in a romper made for men. Yes, it’s fun. It’s also flirty and very different, but that’s what Lollapalooza outfits are made of. Two companies to look out for as you begin your romper rampage are Romper Jack and Harajuku.

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8. Your Future Is Bright

I highly recommend not bringing your new pair, or the set that you have managed to hold onto for the past three years to Lolla, because they will either get destroyed, or you’ll lose them. is a website that exclusively sells music festival sunglasses on the cheap. Your new pair will help reflect the strong sun throughout the eight hours you’ll be breathing it in, and they’re gonna look pretty fresh in those pictures you’ll take.

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What’s your goal with your Lollapalooza outfits this year? Are you going to blend a bandana with your usual get-up, or bust the roof off with a romper? Drop a caret (^) in the comments if this was helpful.

Featured image source:
Collin Andrews

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