I dressed like a millennial for a week (and worried people thought I was in my 30s) (2025)

There are many debates between Gen Z and millennials but the intergenerational warfare reaches its peak when it comes to socks. Put simply: if you still wear ankle socks, you’re most definitely a millennial. If you’ve evolved into covering your ankles, wearing proper-length socks no matter what shoes you have on, then you’re a Gen Z.

It comes down to more than just socks though. Fashion choices in general continue to divide the young from the (according to TikTok) old. For example, skinny jeans are so 2010. And the mom-waisted jeans you think are more up-to-date? Yes those are a total millennial giveaway. Low baggy jeans, that sit on your hips are in. Midi-dresses are also out (especially floral ones). Bright colours left the chat a long time ago. And if you still own a pair of low Converse, I hate to break it to you, but it is time they went in the bin.

And it isn’t even just your clothes betraying your age. How do you style your hair? If you’ve still got a side parting then you’re definitely not in your 20s anymore.

Gen Z, born between 1997 and 2012, have strong opinions. Born in 2002, I fit neatly into this age category, and from what I wear it’s obvious. My ankles haven’t been on show since my parents dressed me (my dad missed the millennial age bracket by five months but he classes himself as one) and I threw my skinny jeans out as soon as I had money of my own to purchase baggy ones.

But, in the spirit of connecting with my old(er) colleagues, for one week I decided to commit to the millennial fashion choices – and see how I really felt, and if it makes a difference to how I am perceived. Does dressing “older” make me look convincingly so? Of course, these things aren’t in my wardrobe, so I hired a select few outfits from Hirestreet that fitted the styles of my parents and older friends.

Starting with sportswear…

I eased myself in with my gym attire. Millennials tend to opt for tight two-pieces – think leggings and a body-hugging top – with ankle socks, while the young crew prefer a baggier look.

I normally go to the gym at 5am, and like a typical young person, always opt for oversized T-shirts, jogging bottoms, or most recently the trend of flared leggings.

This time though, in true millennial style, I wore burgundy yoga leggings with a matching long-sleeved tight top paired with ankle socks from BAM Activewear.

I must say I liked the outfit – and I felt more put together for the gym now I wasn’t looking like I’d thrown on my dad’s hand-me-downs. But the low socks were a firm no. As I started my workout, I was surprised how much a simple bit of air to ankles bothered me. How can those few inches make such a difference to your overall temperature? I will not be repeating this.

Weekend outfits

Next up, was the floral midi dress. With spring approaching, I’ve already seen at least three people (that looked to be in their 30s…) wearing them on my local high street, paired with denim jackets and always clean white trainers. It’s worth noting it’s rare I wear a dress at all, especially a patterned one like this.

I’d always choose a casual outfit, particularly for something like shopping, like athleisure, an oversized jumper and jeans, or a tracksuit.

My boyfriend commented on the fact I looked “different” – I suspect badly from his tone – and I headed out wondering if people would presume I was 10 years older than I am. I got no looks – but I did feel really self-conscious, too overdressed and breezy. I didn’t hate it, but I will only consider wearing this again when I am a decade older.

It was the next day that really took me out of my comfort zone though. For work, millennials tend to look smarter than us casual Gen Z-ers (we cause mayhem with elders who think we don’t take work seriously in our jeans and tees).

Electric blue suit

So I decided to try a suit – not just any suit. An electric blue suit. Right now, neutrals are in for Gen Z. Beige, grey and black clothes, a neutral home interior, and making everything as bland as it can be. It’s Instagrammable and perfect for the “clean girl” trending aesthetic. This suit definitely was not that.

This one got a laugh from my boyfriend. Granted the suit was accidentally one size too big, but it was the colour that threw us. My idea of smart is an oversized grey or cream blazer – thanks Molly-Mae for inspiring my generation – with wide-leg trousers or jeans. This was smart, silk and so very bright. Too bright.

This one also got me looks from the local supermarket owner, who has seen me enough times to know this isn’t my usual attire. It was outlandish, and I was noticeable from a mile away. I barely recognised myself. Admittedly it was comfortable but I felt like a doll that had been dressed by a child.

The ultimate test: the skinny jean

Now I couldn’t go through this week without trying out the ultimate millennial item: the skinny jean.

Although they are now a bit passé, having morphed into a high-waisted “mom jean”, the skinny shape is synonymous with the Topshop-era millennial, defined by thinness and Kate Moss’s “nothing tastes as good as skinny feels”. It couldn’t be more different from the Gen Z wide-leg, body-positive look.

I have history with skinny jeans, being made to wear them as a child by my parents. I remember them being uncomfortable aged 11, and it wasn’t much better now. Why, if I want tight clothing on my legs, would I choose denim when leggings are available?

I paired a pair of blue ones with a rainbow-coloured knit vest, and went out for a sandwich on my lunch break. The main problems, aside from the once-again cold ankles, was the food bloat when I didn’t have the room in my trousers to actually breathe. They were unbuttoned as soon as I got home. The knit vest also felt too small in comparison with my usually oversized attire. I felt like I’d taken advice from a middle-aged teacher on what’s trendy.

I kept wearing them a few times over the week paired with various shirts and T-shirts. I never got used to them and longed for my wide leg jeans that would nearly trip me up with their reams of denim.

To mix things up my final day was filled with leather. I doubled up with leather jeans – skinny, naturally – and a leather fur jacket (there has been a resurgence of vintage leather and fur among Gen Zs, given the rise in second-hand shopping, but it’s not something I own).

I see millennials online call a leather look “timeless”, but I can say that the jeans have had their time. Think Sandy in Grease. I liked the jacket though, if only it was paired with literally anything else.

At the end of my experiment, I couldn’t wait to get back in my baggy clothing, I reflected on the outfits I wore and can confirm I am a true Gen Z when it comes to fashion. I will never get behind skinny jeans, or the side parting that made my head look even rounder than it is and my hair limp and flat.

My conclusion? Whatever people are comfortable wearing works for them, but if you do continue to choose to wear a skinny jean I think you’re quite mad.