Permission to look boring (timeless?) & predictable in New York City

Pack for a four day trip to NY with me

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Denim jacket - Silk Scarf - Black tee - Trousers - Loafers - Belt - Trench coat - White tee - Sunglasses - Sweater - Boots - Bag - Earrings - Jeans - Shawl

I decided to book a last minute trip to spend a few days in New York City for a couple of reasons:

1. I wanted to catch up with some east coast friends

2. I wanted to experience NY in the fall (I’ve done every other season, except fall)

3. I wanted to put my no buy challenge to the ultimate test… visiting New York City without shopping (this will be a seperate post coming soon).

(Please bare with me, as this Substack may come out a little clunky, but I felt compelled to write it nonetheless.)

As I started laying out items on my clothing rack that I really wanted to bring with me, what surprised me the most was everything felt dare I say it a little bland, a little boring, at least in the context of getting dressed in New york.

The Outfits In Question

I’ve always felt my style is much more New York than it is LA, in that I genuinely enjoy dressing up. What some people would label as effort I see as my creativity in full swing. I made peace a long time ago that living in LA means I would be what many people consider ‘overdressed’, but why when I have the opportunity to go somewhere I know I can go all out, am I suddenly choosing pieces that feel a little less celebratory?

New York has always been the ultimate style playground for me. A home away from home. I thought about how I could mix up/dress up the outfits I had planned inside my Indyx app, with the knowledge it would be easy to do so, but something kept stopping me.

For the most part I would say the packing list (15 pieces total) comprises of cake heavy items, with icing that isn’t loud or particularly distinctive. I asked myself: why are these outfits not enough? Why are you questioning them? What was so bad about consciously choosing boring? Is it boring, or is it timeless?

I think this was the predicament. With so much discourse around people not wanting to look the same as everyone else, were these outfits leaning into traditional capsule wardrobe territory? Do these outfits make me look like a carbon copy of every other millennial? And if they do, why is that a problem, especially when i’m intentionally choosing it?

It’s not that i’m anti capsule wardrobes, but I do loath the belief there are certain items we all need to own, in a bid to access that elusive descriptor of ‘timeless style’ and check the box of getting a capsule wardrobe right.

What I consider timeless could be incredibly different to what you do. For instance a trench coat to me truly is timeless. Twenty year old me wore one, as did 30 year old me, and I still wear one as I approach my 40’s, but that doesn’t mean everyone needs to own a trench coat. Many people might consider a pencil skirt timeless, but to me it isn’t.

If I truly love the pieces I wanted to pack and I liked the outfits they would make, why then was I overthinking these outfit choices to this extent? This was a new feeling to me.

I thought long and hard about it, and after recently coming back from a trip to Idyllwild (think cabin in the woods vibes) I realised maybe my need to be creative with my outfits had been fulfilled to a point that I just wasn’t craving it at the moment. The trip to Idyllwild got my creative juices going in such a huge way. I got to play dress up for real life, and it surprised me just how inspired I felt dressing for that trip.

I can’t help thinking does it have anything to do with the fact that dressing up in Idyllwild was solely for me, and no one really saw me. There was no shops to visit that might strike up conversation about what I was wearing, whereas in New York, I welcome the spectacle. I enjoy being immersed in a city where great style is both incredibly diverse and common place.

The more I thought about it, the more I realized I was craving some simplicity. Timeless pieces (whatever that means to you) allow us some mental space, and maybe, this trip wasn’t about being on display.

I have no doubt there will be future trips where my desire to be on display, and to push my wardrobe to new heights will showcase itself. We all get to decide to what degree we want to be creative (and what that even looks like) when we get dressed, and this has been a helpful exercise in reframing what constitutes creativity for me.

After rewatching past episodes of SATC this month, I have no doubt there was a small voice that crept into my subconscious encouraging me to wear a bird on my head, or a gigantic flower brooch because I know those kind of stylistic choices are welcome in a city like New York, but that just isn’t me.

I fully appreciate what I consider ‘bland’ might be very different to what you do, but there is something empowering about owning the choice to dress how you feel in any given moment of time. This feels similar to what I was talking about in the rebellious act of outfit repeating. I know who I am, and I know what I like. Sometimes I do want to push my outfits creatively and sometimes I don’t.

I think there is also an underlying pressure from myself to go all out when I travel somewhere like NY because I live somewhere inherently casual. Kind of like a ‘get it while you can’ mentality, but if I look back over the past few years living in LA, I think I’ve become more comfortable being overdressed here, and so I crave less and less the need to go somewhere else to truly express all of my selves.

My core belief when it comes to style is that play is the most important aspect, and I think writing this I realized I had fallen into the trap of thinking that had to look a certain way, especially in New York. It feels good to be able to check myself, and come back to owning my stylistic choices, no matter what other people want to label them as or make it mean about me.

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