When Should We Step Out of Our Style Comfort Zones?
Knowing when something definitely "isn't me" and when to take that risk.
If, like me, you read fashion articles daily and consume more than your fair share of style-related Substacks by all the brilliant writers that occupy this platform, you’ve probably seen a lot of conversations around personal style. It’s one of those things that should feel really simple… you just wear what you like, right? Well, there’s a lot more to it than that.
Firstly, we have the chat around capsule wardrobes: Everyone should own this piece, that piece and that piece. We have the seasonal trend reports: This is what you should be wearing to be considered fashionable.
There’s a lot of talk around how to know if something is ‘you’, how to buy better, more considered pieces and how to not regret that ‘risky’ purchase (I, alone, harp on about all this enough).
And on the other side of the coin, there’s the discourse around the homogenisation of style and when, in an era of social media and getting dressed for the ‘gram, we’re all actually starting to dress more and more the same. It’s not just social media -
wrote a great piece on how the notion of “investment dressing” (i.e. buying that classic designer handbag, black cashmere jumper or timeless pair of loafers) is contributing to this dilution of truly personal style too.I’ve been mulling over all this for the past few months and it’s led me to ask (myself) the question: How do we find and stay true to our personal style AND leave room for experimentation?
A big part of getting dressed that I personally love is the creative element. I love a bit of extra time to get ready so I can play with different combinations or try styling a piece in multiple ways. Sometimes it’s this trial-and-error process that ends up giving me the looks that excite me the most. But I doubt I would have got there if I’d stuck to rigid ideas about what my style is.
This extends to purchases too. Sometimes I’ll see something in a store or online that I normally wouldn’t look at twice because it “isn’t me”… only to try it on, love it, and it ends up becoming one of the most treasured items in my wardrobe.
I’ve got a few pieces that this happened to me with…
When the risk paid off
Uniqlo U Quilted Jacket
I appreciate this isn’t exactly an ‘out there’ item of clothing but before I got this quilted down jacket, I would have avoided anything like it. Up until this point, my outerwear mainly consisted of tailored coats. I still love that style of outerwear but having this more casual option has been a game-changer for me.
Anna from The Wardrobe Edit wrote a piece a few weeks ago, asking why we buy clothes for lives we don’t have. And the same question works on the flip side: why don’t we have clothes that accurately reflect what we do every day?
This jacket was one of those. It came into my collection a couple of months after I left a full-time, permanent job and ventured out on my own to go freelance. This meant that instead of going into an office every day, I spent a lot of time working from home and heading out to my local park for daily doses of fresh air and a good old stretch of the legs. Turns out this jacket is the perfect piece for exactly that activity.
It’s also been an incredible layering jacket. On the coldest winter days, I’ve popped this on under my oversized coats and it’s taken the edge off, plus it adds more layers to create an interesting silhouette. It’s probably my best example of wavering at first, asking myself if I’d ever really wear it, to it then becoming one of my most-worn items.
Studio Nicholson Lynton Pants
I’ve admired Studio Nicholson for years. That mix of timeless and minimalist designs with silhouettes inspired by Japanese architecture and culture makes for interesting pieces that you can wear time and again, and they’ll still have a bit of an edge. When I saw these trousers in the sale a couple of years ago, my finger immediately stopped mid-scroll. They had an exaggerated curved leg that drew me in. They were navy, so the colour was workable. But still, I ummed and ahhed. Am I brave enough to rock a shape like that? Will they look the same on me as they did on the 5’10” model?
As you can see, I did buy them and I’m so glad I bit the bullet and clicked that purchase button. They instantly lift my outfit with that shape, they make those super casual T-shirt only days look elevated, and I can’t tell you the amount of times I’ve been stopped in the street and asked where they’re from.
Wales Bonner x adidas Sambas
I’ve shared my love for the Wales Bonner x adidas Originals collabs a lot here on The Jones Report. I love how Wales Bonner digs into the adidas archives and puts her own unique spin on them, giving us styles that are both timeless and unique. I know that my Japan trainers and green SL 72s will go with almost any look I put together, I’ll feel good in them, and they’ll become a strong focal point of an outfit.
I look out for the new collections each season and the latest, with its selection of Wales Bonner-ified Sambas, was no exception. I scoured the styles and set a reminder for the morning of the drop. But my usual excitement was dampened somewhat by a seed of doubt: am I a Sambas person? Do I like that folded-over tongue or am I just caught up in Wales Bonner frenzy? I thought back to the amount of times I wore my other WB x adidas trainers (far too many to count) and decided it was worth the risk. I’ll admit the tongue did stump me at first (how do I make this work with trousers??) but now I’m fully on board. Purchase crisis averted.
Cawley Studio Orange Vest
I don’t naturally gravitate towards bright colours. Open up my wardrobe and you’ll see lots of black, navy, grey, various shades of white, a smattering of browns and quite a lot of khaki/olive greens. Let’s just say you don’t need to don a pair of sunglasses before opening those doors, it’s pretty muted in there.
So when I tell you adding a bold orange quilted vest to my collection is a Big Deal, I’m not being melodramatic. But when I saw this Cawley Studio vest on Young British Designers (a great online retailer stocking small, independent British brands), it stopped me in my tracks. I loved the quilted cotton, the front pockets and those three single buttons down the front. And that sleeveless design I could wear on its own or on top of other pieces? I could feel the styling ideas bubbling away instantly. So I cast my notion of “I don’t wear bright colours” aside and took the plunge. Let’s just say I’m very happy I did.
When should you take that style risk?
When do you cross that border from admiration of a piece to deciding you need it in your wardrobe? When do put your ideas of what is “you” to one side and step outside your comfort zone?
If I spot a piece I love but find myself dithering, I ask myself these questions:
What do I like about it? When I analyse an item of clothing, pair of shoes, accessory, whatever it may be, I can start to make sense of what’s drawn me to it. Is it the shape, the colour, its layering potential? Then I can start to think about my next question…
What will I wear it with? If I can come up with a few different outfit ideas using items I already own, I know it won’t actually be much of a risk. But if I’m struggling to picture it with any of my current clothes, chances are it will remain hung up in my wardrobe, never to be worn.
Will I feel comfortable in it? As in, physically comfortable. All of the pieces I listed above are very comfortable in their design, fabric and cut. I don’t feel restricted in them or walk around awkwardly in them because they don’t really sit right. After all, feeling comfortable goes a long way to feeling good in what you wear.
What’s one piece that felt like a style risk that you now couldn’t live without? Let me know in the comments below - and what you love about them!
Any items marked with * have been kindly gifted by brands. All thoughts, picks and reviews are my own.
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Mules were a style risk for me especially those with pointy toes. I was never a fan but then I saw a pair that peaked my interest so I bought them. I’m so glad I took the risk. I love them so much. They are chic yet casual. Just don’t wear them when you need to be somewhere in a hurry.
"And the same question works on the flip side: why don’t we have clothes that accurately reflect what we do every day?"
Love this