Have You Ever Wondered, “How Do I Dress Like Jenna Lyons?”, Here’s Your Answer

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Jenna Lyons, former creative director of J.Crew, has always been a style icon (who can forget the Jenna Lyons era in the 2010s?). From her classic and bold eyewear choices to her perfect business casual outfits, Jenna’s personal style is synonymous with elegance and fun. In the fashion world, her style is pretty attainable. You can replicate her style by dressing up in classic pieces without shelling out on luxury items. If you are wondering, “How do I dress like Jenna Lyons?”, I have everything you need to copy her inspo-worthy outfits.

1. Wear Formal Pieces With Your Everyday Wear

Jenna Lyons streetstyle

Jenna does not shy away from breaking the fashion rules. Whether she is on a photo shoot for her lash brand (LOVE SEEN) or her new TV show on HBO max, you can always catch Jenna dressed up in jeans and blazers put together in a quirky, undone way. Even though pairing sneakers and a suit is the norm now in the fashion industry, it was ground-breaking in 2010.

Copy Jenna’s fun approach on high to low fashion by dressing down a button-down shirt with distressed mom jeans and a sharp blazer. Swap your black oxfords with silver iterations for an eye-catching look. And lastly, don’t forget to accessorize with classic big glasses to nail her look.

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2. Wear Your Hair in a Sleek Bun

Look preppy like Jenna Lyons by wearing your hair in a bun. This hairstyle paired with black thick frames and her classic red lip will help you pull off the Jenna Lyons look effortessly.

3. Add Some Sparkle to Your Outfits

Jenna Lyons Sequined Jacket

During her time as creative director of J.Crew, Jenna Lyons took a new design direction to the brand’s identity by lending her playful style to the catalog chain. It was a successful image overhaul for this clothing company.

If you also want to overhaul your look and dress like Jenna Lyons, add a little bit of sparkle to your outfit with sequins. Who said sequins are only for the red carpet? Depending on your dress code at work, you can channel your inner Jenna Lyons in the office. This outfit would also be a great date night look!

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4. Accessorize With Eye-Catching Heels

When it comes to footwear, Jenna Lyons loves to wear head-turning heels. Not just for special occasions but even for casual walks to get her favorite coffee ice cream! She either slips on sequin accent heels, strappy sandals, blue heels, or classic black pumps.

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5. Rock a Red Lip With Light Makeup

Jenna Lyonns Tuxedo jacket

If you want to dress like Jenna Lyons, you should focus on your makeup look. The former executive creative director of J.Crew explained to Into The Gloss magazine that as she has gotten older, she prefers to not wear heavy makeup.

“I don’t like to wear a lot of makeup because I’m getting older, and when you get more wrinkles, makeup settles into the crevices. It can look heavy. Now I stay away from anything that’s chalky, or dry, or powdery,” she explained.

Her go-to makeup look is simple: natural eyelashes, a red lip (or sometimes an orange-red lip), and no eyeshadow. To copy her look, don’t forget to add natural-looking fake lashes and a bright color lip to your makeup bag.

Get the look:

Related: 10 Ways to Dress Like You Work at a Fashion Magazine

6. Wear Elegantly Printed Dresses

You don’t need to wear a grand Met Gala-styled dress to look like an influential person in fashion. Simply wearing a statement print dress will help you achieve the Jenna Lyons look!

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7. Put On a Tuxedo Jacket

Jenna Lyons tuxedo jacket
D Dipasupil/Getty Images North America

Take style notes from Jenna Lyons and swap your jean jacket for a formal blazer. Pairing your navy pants with a black tuxedo jacket can work for a daring dinner party look. Plus, wearing a luxe tuxedo jacket will make you feel like you are on the cover of a fashion magazine. To get her look, unbutton a few of the top buttons or forgo a top underneath.

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8. Wear Classic and Bold Eyewear

It is impossible to talk about Jenna Lyons’ style without talking about her bold eyewear! Her signature eyewear style is clear Dita aviators. Though this brand is a little pricey, you can easily recreate the look.

If she’s not rocking these shades, she accessorizes with thick black frame glasses. These shades are so versatile and add a perfect accessory to complete all her outfits.

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9. Mix Different Prints

How do I look like Jenna Lyons?

Jenna is adventurous with her prints and this former president of J.Crew always makes daring outfit combinations. Whether it’s leopard print with polka dots or pinstripes with florals, somehow she always manages to make them work.

To achieve her look, mix different prints that have a similar scale. And if you want to balance out your outfit, wear a white shirt and neutral-hued heels to tone down the busy prints.

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10. Wear Shiny Fabrics

how do I dress like Jenna Lyons

One of the best ways to dress like Jenna Lyons is to splash in metallics or satin in your outfits. You don’t have to go for a full monochromatic look, just one or two clothing items will do.

For example, emulate Jenna’s style by pairing a chambray shirt with a metallic or satin skirt. You could also wear a white tee and denim jacket with your satin skirt.

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11. Add Feathers to Your Look

Source: Into the gloss magazine

Jenna Lyons loves to add some glamour to her office looks. And she does this so effortlessly by incorporating statement feathers with office-ready pieces.

One of the biggest challenges and questions most people have with styling feathers is how to not look frumpy or costumey. If you are reluctant to wear feathers, follow Jenna’s lead by pairing statement feathers with timeless jeans and a white button-down shirt.

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12. Slip On Some Sneakers

Jenna Lyons converse streetstyle
Source: Getintothegroove

Jenna is the creative force who made sneakers and office wear cool. Her favorite sneaker brands are Converse and Nike. These sneakers are usually accompanied by a trench coat or an uber-chic wool coat.

Copy Jenna’s style by wearing a camel coat with joggers and white converse sneakers. The casual footwear makes this entire outfit look cool and chic. And lastly, don’t forget to accessorize with clear aviator shades.

Get her look:

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With these tips, you no longer have to ask yourself, “How do I dress like Jenna Lyons?” In a matter of time, you will master all of her stylish tricks!

If you want to learn to dress like other style icons, copy Audrey Hepburn’s chic fashion aesthetic in this next post: Classic Style Tips to Steal from Audrey Hepburn’s Outfits.

Jenna Lyons streetstyle


Hi! My name is Temwa and I have an obsession with all things lifestyle. Whether it's home decor, classy fashion, beauty products, or gift ideas -- you will find me writing about those topics. When I'm not sitting at my laptop, you will find me making press-on nails over the weekend!