THE EFFORTLESS STYLE 101
welcome to the training camp on how to dress effortlessly. Because after all - it's not magic, it's just a bit of practice.
Have you ever had to give a speech in public? Something that felt like a big personal moment or a big career step? You want to deliver the best version of what you would like to express to your audience. If done right, public speaking is the ultimate demonstration of seemingly natural charisma, knowledge and charm.
What is, in the end, entertaining or educative to the audience, is hard work. It’s training. If it looks effortlessly - that is because the relevant person has either practiced their speech a lot and / or is used to public speaking.
Here comes my hypothesis with a drum roll: Effortless style is training, too. It’s - in all its contradiction - effort. Once you’ve found your routine, it’s easier. You’re moving in familiar territory and improvising will, as a result, be easier, too. It’s like going to the gym - at first you simply show up, it’s the daily training that makes you better.
Every single client I ever had in my lookbook bookings on Indyx told me in their questionnaire that they wanted to look effortless. This term is labeled differently, e.g. ‘not too put together’, ‘relaxed’, ‘cool’ etc. But it always targets at the same feeling: Everyone wants to look like there’s no act of intention behind their looks. While looking good. And it’s my number one goal when dressing myself, too.
The good news: There are actual practical tips you can follow.
That’s what we’re here for. First, we’re looking at how to ‘train’ to look effortless, then we’re asking the Substack fashion squad what they’re doing to get the look.
1. TRAIN TO BECOME AN EXPERT IN FIT, SILHOUETTES AND PROPORTIONS
… and what I mean by that is: Become obsessed with fit, silhouettes and proportions. In my personal opinion, it is inevitable for an effortless look to be composed of oversized pieces. Because, and that could be an entire post in itself, effortless equals imperfect.
Alessandro Michele has put it so beautifully in his interview with Bella Freud for her podcast ‘Fashion Neurosis’:
‘Also, being chic is that you have something wrong on a perfect look (…) it’s the secret of fashion I think.’
In terms of oversized clothing, we’ll have to overcome two immense fears here:
a. Especially if you’re on the more petite side, you’ll say that oversized silhouettes won’t look flattering on you. And while this might be true in some cases, you have to forget flattering in favor of effortless. Your outfit can still look amazing and cool, though. If you’re short like me, I recommend reading this Allison Bornstein article for her newsletter ‘Fashion Friend’ (The Cut).
b. You’ll say that you’ll look sloppy. Believe me, with a bit of training, you’ll even look effortless in your most classic office look.
Morenike Ajayi recently did an amazing Instagram reel on the topic of oversized fits which contains wonderful practical advice on the right sleeve and hem length, proportions and shopping tips. So if you want to learn, please start here.
In the process of finding what is effortless to me, I became so obsessed with the fit of my clothes that I measured the perfect ‘effortless length’ of my favorite pieces.
Here’s how to buy new ‘ingredients’ for an oversized / effortless look:
Ignore the sizing label. As I said, become obsessed with the fit.
As a woman, buy in the men’s section. They have more oversized styles, and you’ll instantly get a more undone (i.e. imperfect) vibe because, well, the pieces fit differently.
Add the word ‘oversized’ to the search bar whenever you buy a piece online. Easy, right? And as Morenike Ajayi says: Start by buying the things that are supposed to be oversized.
Here’s what my Pinterest algorithm thinks I find effortless: Mostly oversized pants and layering.
2. TRAIN TO BECOME AN EXPERT IN STYLING
Here’s your training schedule to become an expert at styling the pieces you already own. If you need help, get a personal trainer, aka a stylist. However, I’m sure we all can do these things, too, and they’re all you have to do in the beginning:
Get dressed every day.
Document your outfits in the least stressful way (for me it’s the good old mirror selfie).
Play with the pieces in your wardrobe - while you’re actually trying them on. For instance, learn how to tuck in, half-tuck and how to button a shirt - and learn how to roll up the sleeves.
See how this outfit changes through the styling and fit? From very classy (left, tucked in, sleeves down) to a bit more undone (that tiny bit more loosely tucked in, sleeves rolled up, but still with a belt - second to left) to kind of cool (sleeves rolled up, loosely tucked in, baggier denim) to kind of effortless (far right: sleeves rolled up, deep neckline, only three buttons closed, fully untucked).
3. TRAIN TO BECOME AN EXPERT IN BALANCE
An effortless look is a balanced look. This can mean tension, contradiction, harmony and an undone element at the same time. I think Fanny Adams is doing an incredible job on Substack, explaining outfit formulas. Her latest examples of ‘breezy - breezy - structured’ are mind-blowing - and easy to recreate at the same time. The best other ways to create balance are:
Show skin: Roll up the sleeves, create a neckline, show skin on your feet, your ankles or your wrists, combine shorts with a long sleeve.
Add texture and dimension: Pair leather with denim, pair suede with satin, add a sweater on your shoulder. Add jewelry.
Put effort into styling your hair: Become a professional in two hairstyles for your hair type and face: An undone hair style and a sleek hair style. You’ll need the first for day-to-day looks that are lacking lack a bit of ease, and you’ll need the second for those looks you want to level up.
4. TRAIN FOR YOUR PERSONAL GROWTH AND TRAIN TO CARE A LITTLE LESS
Chronic people pleaser, overthinker and type-a-to-do-list-people, train your personalities to care less. It all goes hand in hand, and I think if you’re more confident (and comfortable) in a look, it already helps. I love this (very cheesy) quote by American writer Gore Vidal - it’s so annoyingly simple but so true: ‘Style is knowing who you are, what you want to say, and not giving a damn.’ Side note: Two of my favorite Substack writers on the topic of personal style and growth are Asta / Aastha and Maureen McLennon Welton.
THE BEST PRACTICAL ADVICE FROM THE SUBSTACK FASHION SQUAD
What is a training camp without experts? I asked some of my favorite fashion writers on Substack what effortless style mean to them, what practical tips they have and who their (effortless) style icon is. I loved how their answers equally supported and added ideas to my hypothesis.
