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How To Build An Anti-Trend Wardrobe, According To A Fashion Director In Her Fifties

"Everything I’m wearing now in my fifties is classic."
Over 50s fashion tips.

As a fashion director, I’m always so excited for the new season collections: to see the new shoe and the new silhouette and the boot of the season, to see what everyone’s doing and what the trends are. But for me, everything I’m wearing now in my fifties is classic. 

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In my wardrobe, I’m really happy to go to work in a great pair of jeans and a great jacket. It may look a little bit boring and repetitive to people but I don’t care because I like it, and it suits me and I feel dressed and confident.  

Your wardrobe becomes quite minimal when you get older, which is really great because I’ve got kids and getting ready in the morning, I don’t want to have to think about it and I don’t want to have to iron anything. I’d rather spend an extra half an hour reading my book rather than workshopping outfits. 

When you’re in your fifties, you want hard-working pieces, good tailoring, and a couple of good dresses. The basis of my wardrobe is a great jean, a skirt, and some staple shirts and sweaters, and then I add to it with accessories.  

I love anything that I can wear on high-rotation: I love to give my things a long life, and I really treasure them. I get all the trends out of my system when I’m styling shoots for the magazine: we just had the Prada pink bow dress and it was so great to put it on the model, but then I was done.  

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My advice would be to not spend a lot on sweaters, but invest in jackets and tailoring. It does take a bit of work to find the right thing, you’ve got to try on a lot of pieces, and think about whether it’s going to work with what you’ve got and the right proportions for your body, but you will find it. 

Look One

Naomi fashion over 50.

The blazer

I opt for a great tailored jacket that’s big but not too oversized, because I have broad shoulders. Something that’s lightweight because of our weather – you can put a thin sweater underneath. The Toteme jacket goes from summer to winter, I’ve been wearing it for years – it’s possibly the best thing I’ve ever bought in my life.

It’s the perfect fabric and oversized but not too oversized. Toteme has some really good pieces for building a good wardrobe because they focus on classics.  

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Naomi’s pick: Toteme Double-breasted recycled woven blazer 

The jeans

I have multiple pairs of jeans on high rotation. These Bottega Venetas are my favourite because they’re super long and they give me a chic polish for work. They’re medium-rise, so I’ll put on a belt and throw on a sweater half-tucked in.  

I love a faded jean, but I don’t feel like the slouchy style really works on me, and I’ve never been a ripped-jean girl. I also don’t usually embrace a high waist because my legs are long, so the proportion isn’t right.  

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I’m also coveting the new Gucci jeans – they could be on high-rotation in my wardrobe in summer because they’re a nice light denim. 

Naomi fashion over 50.

Naomi’s pick: Bottega Veneta medium-washed high-rise straight denim jeans with Celine by Hedi Slimane medium Triomphe belt 

The shirt

This Miu Miu shirt I love – it’s a cropped khaki shirt, which I wouldn’t wear without a jacket but it gives you that great silhouette and it stops you from having to tuck into your waist. It’s practical. 

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Naomi’s picks: Miu Miu cropped cotton shirt 

Look Two

Naomi Fashion over 50

The mini-skirt

I’ll do a bare leg, but the shoe has to be super polished. This is my little Prada mini skirt – it’s a re-nylon skirt, it’s so simple and well-made. 

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Naomi's fashion over 50.

Naomi’s pick: Prada Re-Nylon miniskirt 

The coat

I like a short skirt with a jacket or a three-quarter navy coat because it makes it grown-up.  

Naomi
s fashion over 50.
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Naomi’s pick: Miu Miu double-breasted wool coat 

The sweater

You can buy good, simple sweaters from Uniqlo or COS – I wouldn’t spend a lot of money on a sweater. Save that for jackets and tailoring. 

Naomi fashion over 50

Naomi’s pick: Uniqlo cashmere sweater in black or grey 

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The shoes

Those are Saint Laurent slingbacks, and they’re very ongoing – the heel’s not too high, it’s that classic shape that you can wear for years. 

Naomi’s pick: Saint Laurent by Anthony Vacarello slingback flats

Look Three

Naomi fashion over 50.
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This is the same Prada mini skirt and same Toteme blazer, but I updated the shoe for these little Row suede flats – I love them because they’re so comfortable, which is great for walking around Fashion Week.

The Shoes

Naomi fashion over 50.

Naomi’s pick: The Row suede ballet flats

The Shirt

This is a Dries Van Noten shirt – shirts have become a real staple because they work for summer and winter, Milan and Paris. I like a good quality shirt in a beautiful colour.  

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Naomi’s pick: Dries Van Noten shirt

The bag

Naomi’s pick: Loewe Flamenco clutch bag 

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Extra Wardrobe Staples

The white T-shirt

Naomi fashion over 50

Naomi’s pick: Jack + Jac baby tee 

The bag

Naomi’s pick: Chanel 2.55 handbag 

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The jewellery

Van Cleef & Arpels gold Perlée Perles d'Or bracelet

Naomi’s pick: Van Cleef & Arpels gold Perlée Perles d’Or bracelet

The pants

Fashion over 50, Naomi.

Naomi’s pick: Matteau cotton chinos  

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