A few weeks ago, we introduced you to Aubrey Fry, the senior designer and resident “jeanius” behind J.Crew’s (and Madewell’s!) denim collections. Aubrey’s been on the denim team for more than four years; she’s a real denimhead and our kind of gal, and she was just the person to talk to about the company’s jean ideas before we put our styling stamp on their spring selection. Together with J.Crew, we photographed eight women – a mix of our friends and their creative minds – in two looks (one for day, one for night) mixing the best spring and summer pieces with their own favorites. First up were J.Crew’s Molly Schaul and Tracy Georgiou, in New York, and the L.A.-based fashion editor Lawren Howell and stylist Annina Mislin. This is the story of how it went down…

MOLLY SCHAUL, Point Sur Teddy Buckle Back Jean

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For Molly Schaul, J.Crew’s senior design director of women’s wovens, whom we met in her Chelsea home, we changed things up a bit – giving her a jean she’d never tried before. Though her usual denims are high-waisted (she loves the J.Crew Hightower), Molly always goes for a skinny, and this cropped Point Sur Teddy buckle-back crop style is the opposite of that.

What’s a foolproof way to wear a jean like this one? A way that would look good on everyone…

Always show your waist by either tucking in a top all the way, or half-tucking the front, or wearing a more cropped proportion up top.

What style icon does this jean make you think of?

Annie Hall.

It’s an ideal city jean because _________.

The high waist always makes you look neat and tailored.

It’s an ideal getaway/vacation jean because _________.

The cropped leg is perfect to be barefoot strolling on the beach.

If you could give a pair of these jeans to anyone in the world, whom would it be?

Kate Middleton. Would love to see her a little more undone.

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LAWREN HOWELL, Raw-Edge Stretch Denim Pencil Skirt

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When it came to stylist Lawren Howell, the immediate, obvious piece for her was the white denim skirt with a frayed hem. Lawren, who works with Vogue (including its international editions), has a truly classic look, always polished, but not too much so. Think uptown New York meets Venice Beach, which is where the San Francisco native – who was based in Manhattan for several years – now lives with her husband and young son and daughter in a 1910 Craftsman.

What did you notice first when you put this skirt on?

The shape and length. I love that it’s a straight skirt instead of a clingy pencil skirt, and the it’s a tad in the mid-length zone, which I think makes it feel more modern.

Where in the world would you take this skirt tomorrow, if you could go anywhere in the world?

Todos Santos, Mexico. It’s on my mind. This skirt seems perfect for a beach town kind of day.

Quick, what’s the first thing that comes to mind when we ask you to choose the perfect kind of piece to go with it?

A black cashmere sweater.

If you were going to recommend this skirt to a friend – what would you say to make your case?

I would recommend it to a friend who just bought a fabulous pair of knee-high gladiator sandals so they could own the perfect skirt to showcase their legs and feet.

What’s your denim always-do?

Do tuck in collared shirt.

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TRACY GEORGIOU, Broken-in Boyfriend

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We photographed Tracy Georgiou – the the woman whose job it is to foster all of J.Crew’s great partnerships (Vans, Ray-Ban, Apiece Apart, Edith A. Miller, Comme de Garçons Play, Birkenstock…) – at home in downtown New York. She wore J.Crew’s Slim Boyfriend jean, a Clare V. tee, an indigo-dyed jacket, and Converse for day. And for her night look, a crisp J.Crew tuxedo top and blue suede d’Orsay pumps.

What’s a foolproof way to wear to wear a jean like this J.Crew boyfriend?

With a classic top and a polished heel.

If you had to think of a different name besides “boyfriend” for this jean it would be _________.

The “Everything.”

When it comes to jean cuffs, messy or clean?

Either!

What’s your ideal version of a dressed down denim look?

Feels like pajamas, looks like perfection.

Fill in the blank: These boyfriends are cooler than other girls’ boyfriends because _________.

They are all mine.

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ANNINA MISLIN, Point Sur Shoreditch Selvedge in the Warnell wash

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The J.Crew jean for Annina Mislin? The Shoreditch Straights from the Point Sur collection. On Annina, whom we photographed at home in Silverlake, this jean gives really good “modern boyfriend:” loose and relaxed, yet current.

What did you think about these jeans when you first put them on?

I love how substantial they feel, almost like vintage denim with very little, if any, stretch. I find denim nowadays has too much stretch, which can be unflattering.

Why is this jean a great one for L.A.?

The relaxed style fits perfectly with L.A.’s laid-back aesthetic.

How would the way you wear it change for L.A. versus New York?

I would probably opt for a more polished look when in NY – heels vs. flats, blouse vs. tee, lipstick vs. lip balm.

What’s a foolproof way to wear to wear a jean like this?

With a classic top and a polished heel.

Fill in the blank: A boyfriend jean is better than a real boyfriend (or husband!) sometimes in this way: _________.

They know when to relax.

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Hair and makeup by Amy Chin of Amy Chin Beauty.

For more about our collaboration with J.Crew, or to shop their complete denim collection, go to J.Crew.com.