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As a fashion designer, people assume I spend my days thinking about trends and garments. But the truth is, I spend far more time thinking about women's wants and needs.
For more than thirty years, I've watched women step into fitting rooms carrying far more luggage than just their handbag.
They bring insecurities, old stories, expectations… and sometimes, a surprising amount of self-criticism.
Watch: How to find confidence in what you wear. Post continues below.
After three decades in this industry, I've learnt these seven important lessons about style, trends, and feeling good in your clothes.
1. Forgive the cliché, but size really is just a number.
Women in general don't have a style problem, but many have a confidence one, and often that lack of confidence has been created by years of believing the wrong things about their bodies and the correlation to a number on a tag.
I've watched women reject garments that fit beautifully because the size was larger than they expected.
I've also seen women squeeze themselves into a smaller size simply because the label felt more comfortable than the fit.
Sizing is wildly inconsistent. Every brand grades differently and starts from a different block. A size 12 in one label can be a 16 in another.
The right size isn't the smallest size you can get into. The right size is the one that fits your body today, and it's perfectly normal to vary across sizes even in the same brand.
Personally, even within my own brand, I can differ from a size 14 to 18 dependent on the silhouette or style, and my choice of fit.
2. Your body is not the problem.
I've lost count of the number of times I've seen a woman stand in front of a mirror blaming her stomach, hips, thighs or arms when the real issue was the garment itself.
The wrong rise in a pant can completely change a silhouette. The wrong fabric can cling where it shouldn't. The wrong proportion can throw an entire outfit off balance.
Too often we assume that if something doesn't suit us, we must be the problem, but it's usually just the wrong cut for our shape.
3. Know your proportions.
The women who consistently look stylish aren't necessarily the women with the biggest wardrobes or the latest trends. They are the women who understand their proportions.
They know what they like to highlight. They know what balances their frame. They know which shapes make them feel comfortable and confident, and they lean into that look.
That's not boring, that's trusted — and that knowledge is worth far more than chasing every trend cycle.
Fashion moves quickly. Personal style doesn't need to.
4. Accessories matter more than you think.
Another important lesson is that shoes and accessories matter far more than most people realise. They can take the same dress from office, to holiday, to party and to weekend errands.
I've seen outfits transformed by a different shoe. A belt. A great pair of earrings. A handbag with a little structure….
If you only focus on the garments, then you might be missing the finishing touch that makes an outfit feel complete.
5. Underwear can make or break a look.
And while we're talking about things people overlook, let's talk about what's underneath.
The wrong bra can ruin the line of a beautiful dress. Visible seams can change the way a fabric falls. Poor support can alter proportions entirely.
Sometimes it's not the outfit failing. It's what's underneath it.
6. Stop buying pieces that go with nothing.
We've all done it. Fallen in love with a beautiful item — a showstopper — only to realise it doesn't work with anything already hanging in our wardrobe.
Before buying something new, ask yourself a simple question: Can I wear this with at least three things I already own? If the answer is no, it may not be a "wardrobe warrior". It may just be future wardrobe clutter.
The women whose wardrobes work hardest for them aren't buying endless outfits. They're building collections of pieces that work together.
7. Be curious, try.
A silhouette or colour might fall under your radar and feel strange, but give it a try. That's what changing rooms and refund policies are for!
Stepping out of your comfort zone might be just the lift your style has been crying out for.
What I have always loved about being in the fashion industry, after all these years, is that style has very little to do with age, size or trends.
The most stylish women I know aren't the most fashionable — they simply are the most self-aware.
They know what works and feels like them, and they understand that confidence isn't found in a size label or a trend forecast.
Ali Lennard is the designer and owner of Philosophy Australia , a Sydney-based womenswear label. You can follow her on instagram @ali_lennard .
For more helpful style advice and shopping recommendations, subscribe to the weekly Nothing to Wear Substack, listen to the Nothing to Wear podcast or watch Nothing to Wear on YouTube.
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Ali Lennard
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