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Boomer vs millennial: What my mum thinks of fashion's most eyebrow-raising trends

Boomer vs millennial: What my mum thinks of fashion's most eyebrow-raising trends

Generational battle

Text: Stephanie Boey


Is there truly a generational gap in fashion choices? My mother and I go head to head as we dish out our honest opinions on the most polarising trends.

The whole "Ok, boomer" moment got me thinking: What is going on in the mind of a person who was born in a time so different from what it is today? Yes, the internet was first introduced in the early '80s, but the information available on the World Wide Web then is nothing compared to what it's like today. Also, by the early '80s, boomers would've been young adults, having full-fledged personalities and opinions. 

Millennials were practically raised on the internet, Gen Z even more so. Whether we realise it or not, a lot of our personalities and who we are today have been influenced by what we see on social media. But there must be more to life on the internet for the average boomer than forwarded Whatsapp messages (lol). 

After taking a look at my Instagram feed, and flexing her right as my mother to have an opinion on the clothes that I wear (and how my father dressed me for that matter), I was curious to know what else my mother thought about fashion's most popular trends. In my opinion, a lot of which have been influenced by social media, too.

In the spirit of Mother's Day, I subjected my mum to a list of fashion's most talked-about and polarising trends, to hear her honest opinions on what's fashionable today, and to put the theory to the test—is there truly a generation gap in fashion choices?

Trend #1: Ankle straps over trousers

The millennial mindset: "I. LOVE. IT. Finding new ways to wear existing or classic trends give me so much life! I haven't had the pleasure of trying it out yet though. I will make it a point to try one of these days."

The boomer says: "Hmmm, no. I won't be wearing my trousers with straps bunching the hem of my pants this way."

Score card: An enthusiastic yes from the millennial, and a hard no from the boomer.

Trend #2: The fanny pack

The millennial mindset: "I remember feeling so strongly against it when it started coming back a couple years ago. But not gonna lie, I've warmed up to it. Realised they come in handy at concerts, music festivals and raves."

The boomer says: "Will definitely use. It's functional for keeping important documents and cash, while keeping it close for safe keeping while travelling."

Score card: Both generations are in agreement—fanny packs are very functional.

Trend #3: The neck bag

The millennial mindset: "My opinion of the neck bag is similar to the fanny pack. If it's hands-free, I will wear it."

The boomer says: "Yeah, no. Tried it. Didn't work for me because I don't like the feel of the strap rubbing on my neck as I moved around. A variant would be to wear it draped across the shoulder, perhaps that would be better."

Score card: Differing opinions with the neck wallet. The boomer does not like things touching her neck.

Trend #4: The bike shorts

The millennial mindset: "I repeat—no, nien, nyet. No, thank you!"

The boomer says: "Nope, tried it. I don't like the feel of garments clinging too tightly on my body. When I am wearing one, I have this feeling of wanting to be out of it as soon as possible."

Score card: Ding, ding, ding, we have a winner! This mother and daughter duo are in agreement that bike shorts need to be cancelled.

Also related: "I wore bike shorts for a week"

Trend #5: The square toe

The millennial mindset: "I've never been a fan of square-toed shoes. Especially when they're closed. They remind me of stuffy court shoes that stiff office ladies wear. However, when Daniel Lee repopularised the shape for Bottega Veneta in an open-toed silhouette, I'll admit, he did change my mind."

The boomer says: "Yes, I would actually wear this! Preferably with heels no more than 2-inches high."

Score: A solid yes from both generations!

Trend #6: The hiking sandal

The millennial mindset: "I love mine from local footwear brand Yoke & Theam. They have a thick cushioned rubber sole, making them really comfortable to walk in. I've gone walking in them for hours. No blisters! Also, I like how chunky they are."

The boomer says: "Yes, it's the most comfortable pair of footwear I've ever worn. I've been wearing them almost everyday! Glad to see there are now fashionable and colourful versions!"

Score card: Both mother and daughter approve of the ugly-pretty footwear

Trend #7: The bucket hat

The millennial mindset: "C-u-t-e! And this is coming from a person who has close to zero affinity to hats and caps. I blame my three-finger forehead. Anything I put on my head falls down close to my eyebrows. But, I would wear a bucket hat! Even better if I can find one that's reversible."

The boomer says: "Not a fan, but won't discount using it because they are comfortable. It serves its purpose of keeping the hot sun from burning your scalp on a hot summer day outdoors and sunlight away from your eyes. This would be a better option for me as a functional hat, if made to choose between this and a baseball cap. Though I must admit baseball caps look better on me. But then again, comfort and functionality versus looking good. So, the former wins."

Score card: Alas, strong differing opinions in the hipster headgear. 

Trend #8: Socks and sandals

The millennial mindset: "I love it as a styling idea for photoshoots. There's a soft spot in my heart for geek chic. However, I personally wouldn't wear this trend. If I'm going to be wearing socks, I will be wearing closed shoes."

The boomer says: "I do this on travels. Socks keep my feet from dust, cold weather and sweaty feet. I look funny when I see myself in glass refections, but I'm glad I've reached an age where I'm not bothered with how I look as long as I'm comfortable. There are some nice colourful socks out there! I wear those so when people look at my feet, they can have an amusing laugh."

Score card: The boomer is not bothered with people looking at her feet, while the millennial does not approve of her exposed toes in socks.

Trend #9: The chunky dad sneaker

The millennial mindset: "I used to love this trend as a teenager. Skechers D'Lites in the late noughties were my jam! But overgrown this trend since. I cringe whenever I see them now. My rationale is, if I can't run in them, why bother."

The boomer says: "A walking health hazard! I wore a pair and the heel caught on something protruding on the ground and I tripped. Won't be using them again...ever!"

Score card: Sound logic from both parties on disagreeing in footwear that is not functional.

* * *

Final score: The boomer and millennial agree on five out of the eight trends present. That's more than half in agreement! It appears fashion preferences lean more on mindset and personality rather than age or generation. Looks like boomers and millennials have more in common after all?

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