What To Wear To A Concert: My Gen Z Boyfriend Styled Me & Wow

What To Wear To A Concert: My Gen Z Boyfriend Styled Me & Wow
Photo: Cam Zhang. Design: Sasha Purdy/STYLECASTER.

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Despite the 3,000 mile distance between New York and Los Angeles and a five-year age gap, my boyfriend (23) and I (28) usually see eye to eye. We can, however, disagree on outfits. The generation gap of a mere couple years becomes painstakingly obvious whenever we’re about to go out. He leans towards micro-minis and slinky Y2K sundresses on me, while I can’t seem to give up an oversized blazer look.

My boyfriend (Let’s call him Z) is an East Coast boy with an acute sense of style best described in his own words as “functional, sleek, classic; evergreen with a slight edge”. 

I, on the other hand, am a former New Yorker who just moved to Los Angeles in, and my style reflects a smattering of both coasts. I aim for effortless street-style chic with a hint of glam (I’m known for pairing a white tank with a snakeskin boot), but I’m not afraid to stray away from the occasional pop of color or experiment with a brief trend. 

I decided to let him dress me for an R&B show at Webster Hall during Memorial Day weekend to see what he’d come up with. I’m open to revamping my post-pandemic personal style in my new west coast home. Also, if he chooses an outfit I hate, I figured I could absolutely veto him. Z himself is not only in entertainment media, but in a very cool rock band in Brooklyn, so I was excited to get his thoughts on what my concert ‘fit should be

Courtesy of Cam Zhang.

Courtesy of Cam Zhang.

What My Boyfriend Chose

Before diving in, Z has a disclaimer: “I want to start by saying I think you look good in anything, period.” Z recommends a crop top that shows a copious amount of skin. “The reason isn’t to show you off to Tyler the Creator because he doesn’t want you, but most concerts are hot, packed and sweaty, and you want to wear as little as possible while looking cute,” he says. 

pink crop top


To match with the lighter crop top, Z chose a black leather skirt. They’re functional and durable, keep cool while looking cool, and give your skin room to breathe. Also, if someone were to spill a drink on me, leather is quick to deflect and not soak up the smell of the person’s rum and coke that’s now all down my legs. 

Liquid Skirt


Z went with black chunky shoes to round out the look. “You are at a concert to see and not to be seen; the skirt and the top will do that,” he says. The chunky shoe will allow a bit of height to see over the crowd, but it’s flat to enable dancing for three hours. To accessorize he added a thin choker to match with the leather skirt. Instead of a purse, a small fanny pack is the bag of choice for my phone, wallet and keys. “Due to the patriarchy, you don’t have pockets, so you need a fanny pack,” he jokes. 

coach belt bag

Courtesy of Coach.


Courtesy of Cam Zhang.

What I Would Have Picked

I’m very into lingerie-inspired tops, whether that’s a bra as a top or a corset cami. It’s a fun trend to try out this summer and looks so good with the right bottoms. I’d do a maybe sheer, but definitely lacy black bra as a top. Like Z’s rationale, it provides both comfort, sex appeal, and shows enough skin to not overheat. Oversized blazer optional.

lace up top

Courtesy of Amazon.

Although the patriarchy typically won’t allow me to have pockets, I’m choosing high-waisted semi baggy jeans here so I can forgo a bag. They can be any color, but I’m opting for a tried and true blue denim to contrast with the textures of a gauzy top. The cut should be a ’90s dad jean, because I want enough room for my legs to still feel comfortable while attempting to look like Hailey Bieber. 

High Rise Dad Jean

Courtesy of Abercrombie.

I pick out a chunky heeled ankle boot to finish the look off. Since the rest of the outfit is pretty neutral colored, a fun pop of colored shoes pull it all together while making a subtle statement. Mirroring Z’s reasoning, the slight height, even at an incline, will be enough to last a few hours on the venue floor while giving you an advantage to see the show. Dainty layered gold necklaces help draw attention to the collarbone area since the focal point of my fit here is the top. Small earrings also assist in tying the outfit together without getting in the way of any movement at the show, but otherwise a minimal amount of jewelry will get the job done.

Merit Bootie

Courtesy of Revolve.

Merit Bootie

Z’s choices aren’t what I would conventionally go for, but I gotta say, I didn’t hate them. It’s fun to have a partner who can act as a co-creative director for my outfits, and it’s definitely something I’m opening my mind to. I have faith he will continue proving himself as a fashion connoisseur with another winning ensemble for our next joint event. 

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