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Welcome to Fifth & Finest, a forty-friendly fashion blog with zero frump. Have a nice stay!

Easy to Copy Style Lessons from Our Favorite Over-Forty Fashion Icons

Easy to Copy Style Lessons from Our Favorite Over-Forty Fashion Icons

Flicking through the pages of glossy fashion magazines has been a favorite pastimes of mine for as long as I can remember. But I’ve always been more interested in how those high fashion (read: hideously expensive) pieces can translate into everyday life and the ordinary woman’s budget.

Now I’m a sprightly 42 (for another few weeks anyway), I’m particularly interested to see how some of the stylish women I’ve admired for decades are navigating their 40s, 50s and beyond, from a sartorial perspective.

Now I don’t just have the fash mags at my disposal, but the endless time-suck - sorry, resource - that is Pinterest.

For those of you who’ve been living under a technological rock for the last 10 years, Pinterest is basically a huge visual search engine, within which you can create your own themed digital pin boards and pin away the things you love to your heart’s content. Some pins are purely visual, others link through to articles providing a wealth of information on, well, pretty much everything you can think of.

One of Fifth & Finest’s Pinterest boards entitled “How to wear red”.

One of Fifth & Finest’s Pinterest boards entitled “How to wear red”.

Unsurprisingly, the Fifth & Finest Pinterest boards are all about fashion, jewelry, underwear, accessories and my favorite “style crush” celebrities. The point being that, whatever our age, size or budget, we can take inspiration from these fabulous women for our own style choices.

However, since you probably have a little less time than me to scroll through these lovely pics, I decided to summarize some key lessons for you, herewith:

Lesson 1: Masculine tailoring works whatever your age

Lauren Hutton in a sharp white trouser suit. Photo: Elle France

Lauren Hutton in a sharp white trouser suit. Photo: Elle France

Model and actor Lauren Hutton (75) is such a great example of this. Her signature sharp suits in neutral tones always manage to look both of-the-moment and totally timeless.

Tracee Ellis Ross. Photo: @traceeellisross

Tracee Ellis Ross. Photo: @traceeellisross

Tracee Ellis Ross (46, actor, activist and daughter of THE Diana Ross) also works the trouser suit to epic effect, often styling it with sneakers or other “street” accessories for a more edgy look.

Lesson 2: French girl chic is legendary for a reason

And you don’t have to be French to channel it, thankfully. Case in point: Sofia Coppola.

Sofia Coppola looking effortlessly cool. Photo: Vogue

Sofia Coppola looking effortlessly cool. Photo: Vogue

Yes, she lived in Paris for a while and is married to a Frenchman (musician Thomas Mars), but the director was born and brought up mainly in the US. If you’re old enough, you’ll recall some fashion (and acting) faux pas on her part from the early 90s. But like most of us, at 48 she’s evolved and truly developed her own look, borrowing heavily from the ladies of Paris: cigarette pants in black or navy, stripy or geometric print tops and blouses in neutral shades (or subtle pops of color) finished with artfully “undone” hair and make up. Plus a fabulous line in midi day dresses.

This truly is a master class in chic which you could easily copy with some much cheaper pieces from Gap, Whistles, J Crew etc.

Lesson 3: Mixing prints and patterns isn’t just allowed, it’s encouraged

Maggie Gyllenhaal working multiple patterns in monochrome shades. Photo: Getty Images for Marc Jacobs

Maggie Gyllenhaal working multiple patterns in monochrome shades. Photo: Getty Images for Marc Jacobs

The luminous Maggie Gyllenhaal (41) and Jenna Lyons (former creative director of J Crew, 50) are masters of this skill. And it is a skill, albeit one you can perfect with relative ease.

Jenna Lyons mixing florals and stripes to fabulous effect. Photo: Mike Coppola/ Getty Images

Jenna Lyons mixing florals and stripes to fabulous effect. Photo: Mike Coppola/ Getty Images

Stick initially to only two different prints per outfit and pick colors which tone, even if they don’t “match”. As you become more confident, clash up a storm if you like.

Lesson 4: Color is your friend

Naomi Watts at the Met Gala in 2010. Photo: Everett Collection/ Shutterstock

Naomi Watts at the Met Gala in 2010. Photo: Everett Collection/ Shutterstock

Neutrals will always have a principal role in your wardrobe, but don’t fear color, especially as you get older. It can bring an outfit bang up to date and, frankly, brighten up your day.

Tracee Ellis Ross (again) uses color like a champ. But, for a slightly more conservative example of color use, look no further than Naomi Watts (50 - really!) who rarely steps out in all-muted tones and always looks spectacular, whether on the red carpet or running errands.

Tracee Ellis Ross making golf-inspired fashion look chic. Photo: Getty Images

Tracee Ellis Ross making golf-inspired fashion look chic. Photo: Getty Images

Michelle Obama rocking a bright purple pant suit. Photo: 2019 Paras Griffin

Michelle Obama rocking a bright purple pant suit. Photo: 2019 Paras Griffin

Another color expert is Michelle Obama (55). Since leaving the White House she’s been able to indulge her more playful side and has recently rocked a series of epic, brightly colored trouser suits.

Experiment and see what works for you, but reds (from rust to corals) and yellows (lemon to mustard) are great places to start. Find your jam.

Lesson 5: …So are accessories

Jenna Lyons’ statement glasses. Photo: Jared Siskin

Jenna Lyons’ statement glasses. Photo: Jared Siskin

From Jenna Lyons’ heavy-rimmed specs to Debbie Harry and Lauren Hutton’s classy use of hats, a signature accessory can elevate and pull together your look with minimal effort and expense.

Debbie Harry in a wide brimmed hat. Photo: Victor Demarchelier for Vogue Spain

Debbie Harry in a wide brimmed hat. Photo: Victor Demarchelier for Vogue Spain

Lauren Hutton styling a boater hat. Photo: Ron Gelella/ WireImage

Lauren Hutton styling a boater hat. Photo: Ron Gelella/ WireImage

Some accessories require confidence to to truly work, so they’re really made for the older women who, frankly, gives less of crap.

Lesson 6: Less make-up is usually more

For reasons I still can’t work out, heavy make up can be aging and is best left to the younger crowd. Naomi Watts, Sofia Coppola and Chloë Sevigny (44) do natural in a stunning way.

Chloe Sevigny in barely there make-up. Photo: David Adesida

Chloe Sevigny in barely there make-up. Photo: David Adesida

Sofia Coppola’s natural, rosy look. Photo: festival-cannes.com

Sofia Coppola’s natural, rosy look. Photo: festival-cannes.com

I realize sometimes a “natural” look can take time, energy and product but, in my humble opinion, the result is a more flattering, glowing look. And let some wrinkles shine through. Embrace them.

Lesson 7: Shorts, minis and tight dresses are never off limits if you enjoy wearing them

I know she has what we can all agree are stunning legs, but Chloë Sevigny still rocks a pair of shorts as well - or even better - than she did in her 20s. And not just because of the legs, but because of her confidence and comfort in her skin and her style.

Chloe Sevigny owning the denim cut-off shorts. Photo: Getty Images

Chloe Sevigny owning the denim cut-off shorts. Photo: Getty Images

Beth Ditto of The Gossip (38) dresses her curves in many a body-con dress and always knocks it out of the park. Her rock-chick sensibility (backed up by, you know, actually being a rock chick) and chutzpah mean she always pulls it off.

Beth Ditto in a big cat print dress and hat. Photo: Film Magic

Beth Ditto in a big cat print dress and hat. Photo: Film Magic

Lesson 8: Do you

Part of the joy of growing older is getting to know yourself and your style better. Work with that, regardless of whether it’s strictly fashionable or on-trend.

Zooey Deschanel doing her thing. Photos: Getty, Bauer Griffin

Zooey Deschanel doing her thing. Photos: Getty, Bauer Griffin

Zooey Deschanel (39, I know, how is that even possible?) is a great example of this. She has a cutesy, quirky style which has evolved over the years, but is still undeniably hers and looks fabuous.

Maybe you’re really into the vintage pin-up look which works wonders for your body. Go for it.

Maybe you like the more boyish, minimalist style. Work it.

The ultimate culmination of this lesson is that, if none of the other lessons resonate with you, file them in the trash and just do you. No one else does it as well.

I’d love to know who your style icons are and what you’ve learned from them. Or maybe you have some lessons for them? Do tell.

And check out the Fifth & Finest Pinterest boards if you need any inspiration. I’m always open to suggestions for new boards too…

























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