In Partnership With
How to Wear Classic Pieces (in a Not-So-Classic Way)

In partnership with Ralph Lauren.

Women’s magazines are always espousing the benefits of building a wardrobe replete with classics — black pants, white shirts, a trench coat, etc. I typically reject this for a host of reasons, least not being that I own exactly two pairs of black trousers and have never, not once, worn either. Yes, it would be easier to get dressed if I didn’t feel this nag to look like a piñata every time I left my home, but I am who I am.

Of course, what works for me won’t necessarily work for someone else, but as my personal style evolves and a curious urgency to own more “adult clothes” sets in, I’ve been rethinking the whole classics thing. Particularly in that I’d like to wear them more. But not in the prototypical way — no, no. Owning classic pieces doesn’t necessarily mean that you have to look classic. If you have enough accouterments in your wardrobe, you can jazz up just about anything.

I used key pieces from Ralph Lauren’s Iconic Style collection to develop three looks to prove my hypothesis correct. Here, let me show you.

Item 1: A utility jacket — commonly worn casually with jeans and a T-shirt, right?


Wrong! Now I know what you’re thinking: what’s the big deal? She seems to be wearing some regular corduroy trousers and, granted, those flashy fingerless gloves, but I ask you to consider the following:


Wam-bam thank you ma’am. Under said utility jacket lay the answer — a metallic button-down styled as a tube top, festooned with layered gold necklaces. Classic, run-of-the-mill pieces? Indeed. One-in-a-million style? You betcha. (I’m sorry, I had to.)


Ralph Lauren utility jacket and loafers (styled with A.W.A.K.E, pants, Azzaro metallic button down from The Real Real, Aurélie Bidermann jewelry and Gucci gloves)

Item 2: A camel coat, or the artist formerly known as the unofficial sartorial mascot of businessmen worldwide.


You can wear your work clothes under your work coat, or you can tie your trench coat (another classic) like it’s a dress, wear it with green shin-length socks (to maintain the businessman vibe) and matching satin shoes, then tie a ribbon around your neck, strap jovial beaded bracelets on your wrist…


And call it a day.


Ralph Lauren coat (styled with a Céline sleeveless trench, Manolo Blahnik shoes, Falke socks, Krewe sunglasses, Aurélie Bidermann and Simon Miller bracelets)

But first you should dance your way to the jukebox to prove the naysayers wrong.

Item 3: The thick, cashmere knit turtleneck


Is it fair to assume we’ve all been confronted by the strong desire to own some permutation of this Ralph Lauren sweater? Maybe it was a pipe dream whereby you wore it with your favorite white jeans and knee-high boots.

But why do that when you can do…


Ralph Lauren sweater (styled with a Rosie Assoulin skirt, Christian Louboutin shoes, Judith Leiber clutch, Khiry hoop earrings, & Other Stories socks)

This! And by this I mean hold a jewel-encrusted zebra in one hand while popping your argyle sock-wearing ankle out with your opposing leg.


Sweaters can be worn with just about anything, so why is it that we always default to jeans or trousers? What about a huge patent leather skirt? Or, say, a sequined dress? Just a thought starter.

Conclusion? Classic pieces — the basics that serve as a foundation for our wardrobe — are great! You’ve just got to know how to push back when they ask for anything less than brilliance.

Styled by Leandra Medine, photos by Krista Anna Lewis. Shot at Mr. Fongs

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  • I find all 3 outfits wonderful – simply the best.

  • YES X1000000000000000000!!!

  • ella

    ~fangirling over here~ This article especially hit home for me! I’ve always dressed on the more eccentric side and when I started working at RL as a copywriter, I’ve noticed my style shift into this new sense of classic you’ve illustrated here– taking timeless pieces and adding that unexpected just-right, modern spin. These outfits have my heart on the floor, thank you MR! <3 <3

  • Natalalaa

    SHE. IS. STUNNING! (Sorry for the caps lock…not)

  • Zoe

    Only Leandra can style elbow length, metallic gold, fingerless gloves casually. I never knew I needed them until right this instant.

  • Ally H

    Just want to say I noticed the use of “wam bam thank you ma’am” in two of your most recent stories and I truly appreciate this as I myself have been trying to bring back this phrase but to no avail

  • Lanatria Brackett Ellis

    Heels and socks forever!!! *fist in the air

  • Grace

    One of my favorite photoshoots of yours ever, the styling is beyond. Amazing work!!! xx

  • chouette

    YESSS so so much yes! Slide 17 is so American Vogue heydey to me, totally loving it. This is all I want my personal style to reflect – you’ve actualized capital-F Fashion in looks with good ol’ American classics without looking like an overstyled Talbots shoot! ME WANT MORE!

  • Amy

    She looks amazing in all of the outfits! Love the inclusion of the heels/socks trend.

  • Hannah Cole

    Yesssss. I just love workwear for the brave. Challenging the day-to-day humdrum with a bit of sartorial excitement!

  • Let me live at no.17, do not come and get me.

  • The best way to wear classic pieces is to wear them in a -not-classical manner.

  • ashley

    A trench on a trench? You are heaven lm

  • The Rosie Assoulin skirt in look 3 is giving me life and taking my breath away at the same time.

  • Brilliant!! Obsessed with the gloves in the first look

  • Chloe

    Amazing shoot! Saying thanks with all my heart tho bc I could NOT remember the name of this bar but recognized it from a date where I had a very bad kiss.