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.
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’redoing 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.
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
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 my findings. This is the biggest advantage because a. the sizing tables on websites actually do help me now and b. it’s personalized and I know I love these fits on me.
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
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
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.
These are all great examples of very classic looks that have something effortless to them because balance was added: 1. Sophia Roe is in a classic leather jacket and striped suit pants. Her sleek hair balances out the cool leather jacket and her flip flops show skin so there’s a bit of a relaxed vibe, too. 2. A classic blazer turns into an effortless piece when it’s more oversized. The textured leopard bag and flip flops create texture and a casual feeling. 3. Also, very classic: White shirt and black pants. The textured, shinier tote bag anchors the otherwise flat look. The unbuttoned shirt is a bit “je ne sais pas” - undone in it’s most literal sense. Image sources: 1 / 2 / 3
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
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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.
Effortless style is all about feeling good in what you're wearing. I find when I try a "trend" or piece of clothing that I don't feel good in, I look awkward and uncomfortable. But those pieces that feel like "me"? I feel incredible in them - and, importantly, I don't look as though the clothes are wearing me. My version of effortless looks a little undone, rather than polished and perfect. It might be an oversized shirt that isn't "perfectly" tucked in, hair that's been air dried and is a little fluffy, or a big coat with the sleeves pushed up.
My tip for dressing effortlessly is to spend a bit of time thinking about what outfits or items of clothing you feel best in. Was there an event you went to where you wore a dress you loved so much, you barely thought about it and just fully enjoyed the moment? Was there an item of clothing that made you feel really confident during a big meeting or job interview? You'll probably start to see a pattern, which will help you figure out what kind of shapes, fabrics and fits you love wearing most.
(For inspiration on effortless style) I always gravitate towards Sarah-Linh Tran, the co-artistic director of Lemaire. She has a distinct style and you can tell she knows what she likes, and knows when to avoid pieces she doesn't. She always has an "undone" element too, so it never looks like she's trying too hard.
Effortless style, first and foremost, means dressing in a way that looks and feels like you. When what you wear feels and looks like you, confidence follows, and that ease is the essence of effortlessness.
If you’re having a difficult time identifying your “style,” or the pieces that make you feel confident, experiment and document. Take outfit photos to look back on, and rewear the clothes that feel good. Outfit repeating and effortless style go hand in hand. Also, a kind and open attitude makes any outfit look effortless. ;)
I love Charlotte Casiraghi and find her so effortless and chic. She also gives the best book recommendations.
When something feels effortless, there’s an ease to it. There’s in-built comfort, it feels ‘right’ for whatever you’re doing and your surroundings, and it's practical too. It’s easier said than done, and I find the outfits I feel most effortless in aren’t my first attempt. The output feels effortless, but there’s a whole lot of thought and tweaking that’s gone into it! Sometimes I need to play a bit before I get there. Once I find the right formula, it’s easier to riff off again in the future, and that’s why outfit repeating is so darn good.
You don’t need to reinvent the wheel every time. Home in on an outfit you liked and tweak one thing, even if it’s a small touch, like jewellery. Switch the bag, change how you’ve styled your hair, add a pendant. Keep the whole darn outfit the exact same! If you’re struggling to find a starting point, take what you wore yesterday.
Whenever I see Kelly’s or Reva’s outfits on here I always think, ‘Damn - that’s it!!!’. They look comfortable, there’s that in-built ease and both have such a clear POV of their personal style. I think it resonates so much with me because they both have young children too, so I can see their reasoning in their choices, and I’m always down for an outfit that feels effortless and chic, but will inevitably end up covered in sticky fingers and watermelon juice.
To me, effortless style is a gentle rebellion against forcing, rushing, or conforming.
The “effortless” vibe involves being a little bit lazy and allowing things to just stretch out a little bit more. It’s the art of lingering, applied to personal style. It means taking the extra time and space to really feel into how you want to feel (your mood), and where you have to be/go (your environment). It means tuning in and relaxing first, choosing and styling second. You can’t achieve “effortless style” if you’re stressed out! Just like learning a new language, effortless style comes with repetition. It’s a daily practice of noticing… until it becomes your second nature.
What effortless looks like most days: an oversized shirt with rolled-up sleeves, a big bag, black drawstring cotton trousers, and a pair of polished ballet flats.
(My best practical tip would be to) give yourself a little bit more time so you’re not rushing. Listen to what you feel when trying something on: do you feel relaxed, or constricted? It’s all about the small adjustments. Roll up your sleeves. Or unbutton your shirt. Or roll up your trousers at the waist or cuff them at the ankles. Just one little adjustment can give your skin some literal breathing room, making you feel instantly more relaxed and looking effortlessly chic. When shopping, always try on two sizes: the looser size might give you exactly the ease you want. Don’t buy anything that feels constricted and too tight. Take your time to shop and listen to your inner knowing. Play with your existing wardrobe and notice what makes you feel “you”. And allow yourself to be a little bit lazy and go for the path of least resistance.
I don’t have a style icon. But I have a personal mantra: “I always give myself the best”.
When I first tried to name my style words I really wanted “effortless” to be one of them because it connoted (for me) this idea that someone would look super chic without trying; like perfectly undone hair. Since then, I mentally rebranded “effortless” into “eager” because I’m always going to be someone that approaches style with enthusiasm and interest. The best outfits might look effortless but I know they took some thought (just like perfectly undone hair!).
My advice will sound very counterintuitive but if you want to look effortless TRY different things. Get excited about TRYING different outfit formulas or styling ideas because eventually it will help you know your style better. And then you might just appear “effortless” to those around you because you are really “at ease” in your style.
My answers are style icons that so many people share; Zoe Kravitz, Katie Holmes, Jennifer Lawrence. What they all have in common is that they have some really great outfit formulas they seem to fall back on (which you’ve touched on in your Style Notes!). BUT I happen to know that they have all worked with stylists, too! I have to think they did so because they are eager to look good in their clothes!
This outfit is the epitome of my eager effortlessness. I posted this photo recently and the comments were so sweet about how effortlessly cool the look is. I couldn’t help but smile and confess that this was the 4th outfit I put on that morning trying to decide what to wear! It took a lot of effort!
Effortless, to me, is really about comfort. Being comfortable physically, and with yourself. We all put effort into getting dressed … anyone who says they don’t is probably lying. But there are different kinds of effort. There is being intentional, and there is trying hard. I just wrote a Substack about this actually. Effortless style to me is about being dressed and not having to fuss over what's on you, wearing clothes instead of clothes wearing you, imperfections, patina. Like an oversized tailored coat that looks like it was passed down to you and has a story to tell. But as much as it's about being physically comfortable in what you are wearing, it’s also about the mental comfort in who you are. Being comfortable in your skin and self assurance. Wearing what you want. Getting dressed for yourself, and not just because you are seeking a certain validation from others.
(My practical tip would be:) Be comfortable, and dress with function. If you put something on and it doesn’t feel like you, the whole outfit feels wrong… it becomes effort. The second you make a small tweak and land in something that does feel you, your whole body relaxes. I think that shows instantly. A small tip I give clients as a sort of ‘check’ is to make sure you are not wearing an outfit of all new clothes. I always feel the most effortless if I am wearing at least one old, lived-in piece. And the waist on your pants should be comfortable. When a client puts on a pair of jeans or trousers and say they will fit better when they lose 2 pounds, those are an immediate toss. You cannot look effortless if you can't breath.
Honestly, I feel a little lost in (naming a style icon) lately. Effortless to me is less about the clothes and more about who’s wearing them...when style feels like an extension of who you are. The same outfit can look forced on one person and completely natural on another. Zoe Kravitz has long been a favourite. Alexa Chung. Both wear what they want and make it their own. In my early 20s, Sienna Miller and Kate Moss in their Glastonbury era completely shaped how I thought about style. To me, they dressed so effortless: rule-breaking, cool, and full of vibes. Wearing what they loved. I also admire Ilona Hamer, one of the founders of Matteau. I love classics and heritage pieces, and her style feels really personal. She seems deliberate about what she wears (and creates for Matteau), which I think is the ultimate form of effortlessness. The more deliberate you are with what you have in your closet, the less effort you have to put in when it's time to get dressed.
Danielle Goldberg has also been a big reference for me in terms of effortless style. Never wearing too much at once. Great basics. Interesting shapes. Intentional choices. And a personality piece here and there.I remember recreating one of her outfits in 2018 from a screenshot I took from her sister's instagram. I think it was an outfit she wore to her bridal shower or something (I feel so stalkerish, but my memory for a good outfit knows no bounds!). She wore a cardigan as a top with trouser shorts, a monochromatic look, with dark polish on her toes. At a time when everyone else was showing up to bridal showers in frilly white dresses that they bought to wear once and light pink nails... she looked casual, chic, and completely herself... while still respecting the dress code (important). And that’s really what effortless style is to me.
Dressing in a a way that feels yourself, no matter where you are going. and definitely never ever buying something just to wear it once.
The good news is: This effortless look we all want, it’s achievable for everyone. The surprising news: It might take more effort to look effortless than you might have thought - but it’s definitely worth it.
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Anika, you had me hooked from the first few sentences. Don't laugh, but I think of this as the American Ninja Warrior effect - I used to get sucked into that show and by the end of an episode almost believe that I too could scale a vertical wall in 10 seconds because the contestants made it look effortless. So many great tips here (having something "wrong", buying men's, wearing oversized, documenting outfits, etc) and I loved reading some of my favorite fashion writers POVs on dressing effortlessly :)
Excellent article, Anika, thank you for featuring some of my faves! Effortless is a myth - everything takes effort, and as noted, it take practice! Dressing, trying new things, failing (failing!) - these are all important in our learning and growth.
Anika, you had me hooked from the first few sentences. Don't laugh, but I think of this as the American Ninja Warrior effect - I used to get sucked into that show and by the end of an episode almost believe that I too could scale a vertical wall in 10 seconds because the contestants made it look effortless. So many great tips here (having something "wrong", buying men's, wearing oversized, documenting outfits, etc) and I loved reading some of my favorite fashion writers POVs on dressing effortlessly :)
Excellent article, Anika, thank you for featuring some of my faves! Effortless is a myth - everything takes effort, and as noted, it take practice! Dressing, trying new things, failing (failing!) - these are all important in our learning and growth.