Becoming a timeless fashion icon

On how to figure out your style in your 30s.

When you turn 30, somehow a lot of things change. I can already see people in their 20s rolling their eyes at that statement, but trust me. I didn’t want to believe this either. I ignored everyone who said something like it, but they were right.

Not only does your body change (not much, but a little), your mind somehow changes too. You suddenly stop caring about so many things that were vital to you just a few years ago. Having the freedom to go party all weekend? Nah, let’s use the weekend to do some gardening. Skipping the pasta, because you want to fit into your favorite dress at that wedding you are invited to? No, you will forsake clothing sizes altogether and eat that whole package of fresh pasta in one go that is supposedly three portions (btw, who made that stupid decision?).

I don’t know if your frontal lobe can develop twice, or complete an update once you hit 30, but your brain just changes. The biggest change for me was my sense of style. Sounds trivial, but I spent a great deal of time in my 20s figuring out my “style” - and I never figured it out. You have to understand, fashion and I are not the best combination. I struggle with trends, I don’t understand how certain things are considered a trend. Most of them just look downright uncomfortable. Skinny jeans, t-shirt, sneakers - that’s my go-to outfit.

While many things got easier once I turned 30, standing in front of my closet and choosing an outfit for the day became the hardest thing I had to do each day. Because the current fashion industry is not made for people like me. They expect us to have it figured out by the time you are 30. Clearly, a frontal lobe upgrade I never got.

Unsplash, by Toa Heftiba

In a desperate attempt to figure myself out, I turned to social media. What a mistake that was. I was left more confused than ever. Every influencer kept recommending the same 10 outfits and the same brands. Everyone had the same body type (not mine) and their outfits either didn’t fit or made me look like a tent or a stuffed sausage (a German idiom, not sure how well that translates).

And then, the algorithm gods answered my prayers: I was presented with timeless fashion icons like Carolyn Bessette-Kennedy and Jane Birkin.

At first, that didn’t feel like an answer to my problems. Because whenever someone mentions a timeless fashion icon, my immediate thoughts are: Looks nice, but I could never wear that running errands.

But some icons make the casual outfit look like the coolest outfit on the planet. And that was exactly what I was looking for. What I wanted to achieve was to be comfortable, to feel like myself, and maybe make me feel even better than myself, more confident. But what exactly does make a timeless fashion icon?

I am not sure where I read or heard it, but someone said: “Timeless fashion does not mean wearing the same style for decades. It means adapting your style with each decade, but still looking and being yourself.”

So I went into the internet archives, looked through old articles in fashion magazines, and analyzed my old Pinterest boards where I have been saving fashion inspiration for over a decade now. Whose pins have I saved consistently over the years? Which celebrity outfit do I remember even years later?

Here is the (non-complete) list of fashion icons for the non-fashion girlies:

• Alexa Chung: She is the first one that came to my mind when I decided to write this piece. The Mulberry Bag was THE it piece when I was in high school. No one could afford it, but Alexa manages to wear the same style throughout the years, and change it only here and there. I feel like she is mixing vintage and contemporary pieces and always adds a little playful twist, like a pop of red or adding a nice bag to an otherwise casual outfit.

  

• Princess Diana: I never understood the women in my life who loved Diana. I was a kid when she died and as a 6-year old I couldn’t understand why everyone was so sad about a person they had never met. But now, as a 33-year-old woman, I do get it. From all angles, Diana has something about her that no one else has. And on top of that, her sense of fashion is a mastered art of mixing high fashion with relatable, off-the-rack pieces. But what stands out to me is the mix of oversized and tight-fitting clothes. The oversized crewneck sweater with biker shorts, the straight jeans with the oversized knitted sweater.

  

• Sienna Miller: Sienna Miller is another British fashion icon who has to be on this list. I didn’t really have her on my radar until I saw her in Anatomy of a Scandal (great show btw) and in that show too, she had this elegant yet casual style. I love her relaxed silhouettes and the little pop of color. And I am a sucker for an overstuffed bag (looks cool, but sucks when you are the one carrying it). She also mixes tons of neutral colors together, something I am always worried about, but maybe I shouldn’t be?

  

• Diane Keaton: One of my favorite actresses. I love how her style somehow remained the same but updated over the years. The first two pictures could’ve been taken that same week. Similar hat, something around the neck (tie or scarf), an oversized silhouette, and neutral colors. But the pictures are taken roughly 50 years apart, showing she's always stayed true to her unique and comfortable aesthetic. The second picture is from the set of Annie Hall (1977), wearing an outfit she chose herself. The first is a more recent picture of her (I believe). But what stands out to me: is no pop of color. Ever. And somehow none of her outfits are boring, the big belts, the hats, the scarfs and ties, the relaxed and casual silhouettes - that’s what makes her outfits timeless.

  

• Meryl Streep: Another one of my favorite actresses. And for some reason, the first thing that comes to mind when I think of her is her hair! Whenever she is just out and about, her hair has a life of its own, without ever looking out of place. How does she do that? And her outfits somehow reflect that. It is all mixed together (oversized blazer or coat, straight jeans, or maxi skirt), but it still looks cohesive. What stands out to me the most is how every outfit fits her figure, is still oversized, but yet never completely form-fitting.

  

• Carolyn Bessette-Kennedy: I had never heard of her before she showed up on my social feeds. Upon research, I realized she died incredibly young (she only turned 33 years old, what a tragedy). But what captured me instantly was her minimalist but casual style, which almost always includes the same pieces over and over (bag, jewelry, sunglasses).

  

• The Olsen Twins: The Olsen Twins might seem an odd choice for some, but The Row I one of the only high-end brands I could actually consider myself purchasing from. Especially their banana bag (I bought the COS dupe a while ago) has gotten to me. What I take away from their style: monochromatic looks, and choosing an either oversized or somewhat tailored outfit.

  

• Jane Birkin: She is the fashion icon in my opinion. Having one of the most popular bags named after you? Iconic! What I love most about her style is her effortlessness. It often is just jeans and a shirt and at first, I couldn’t figure out what makes it look so different from me wearing jeans and a shirt. But she always adds one piece that makes the entire look different. A pop of red, high-heels to an otherwise casual outfit (she did that more when she was younger I found), an interesting texture or shape (e.g. lace blouse), an oversized chic bag.

  

• Victoria Beckham: Our favorite spice girl and fashion icon. While her style is more business-y than I usually like, I noticed how each outfit is still casual. She dresses a suit down with sneakers, mixes a silk skirt with a casual cardigan and long boots, and wears an oversized sweater with tailored pants. The mix between casual and tailored is what makes her look each time.

  

This is how you become a timeless fashion icon: A checklist

After this analysis, what am I left with? In the end, I only want to take inspiration from these looks, and not copy each outfit. But these are my key takeaways on how to become a timeless fashion icon.

• Play with Proportions: Mix oversized and tight-fitting clothes together to create a relaxed, casual silhouette, that includes somewhat of a tailored look.

• Keep it simple: The base of your outfit (just the clothes, no shoes, bags, or accessories) should be simple, almost minimalistic. That can mean different things:

  • embrace neutral colors

  • make it a monochromatic look

And my two biggest takeaways

• Add a little playful twist:

  • Include a pop of red (shoes, handbag, scarf)

  • Add a nice and chic bag to an otherwise casual outfit

  • Carry an overstuffed casual bag

  • Add a big belt, a hat, or an interesting scarf

  • Add the opposite style shoe to the outfit (e.g. sneaker to tailored suit, high-heels to a jeans and t-shirt look)

  • Make the look interesting by adding a piece with a bold texture or unique shape

• Statement accessories: Have statement accessories like jewelry, sunglasses, belts, hats, etc. and use them in your outfits over and over.

XOXO
Annika