Some Thoughts on Styling Boyfriend Jeans

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Every post, I have to make a conscious effort to avoid discussing the weather. Mostly because I sound like a broken record — it’s cold, we’re all miserable, and I’ve forgotten how sunshine feels.

Instead, let’s consider the boyfriend jean. (If I can’t be in a sundress, I may as well be in the most comfortable pair of pants on the planet, right?) But here’s the trouble with boyfriend jeans — they can look sloppy, especially if paired with a clunky, flat shoe. Here’s how I wore them:

Blue Coat: Karen Walker (Consignment) | White T-Shirt: The Row (Consignment) | Navy Shirt: Nordstrom | Jeans: Madewell | Shoes: Prada (Saks Off Fifth Outlet) | iPad Base as Clutch: Coach | Sunglasses: Ray-Ban
Blue Coat: Karen Walker (Consignment) | White T-Shirt: The Row (Consignment) | Navy Shirt: Nordstrom | Jeans: Madewell | Shoes: Prada (Saks Off Fifth Outlet) | Belt: Club Monaco | iPad Case as Clutch: Coach | Sunglasses: Ray-Ban

The outfit walks a tightrope between casual (thanks to the weekend warrior uniform of jeans and T-shirt) and formal-but-funky (mostly due to the brightly colored shoes and coat).

This is one of those outfits that screams New York to me — not fussy or uncomfortable, but the combination still makes a huge impact. My inspiration was a Bazaar photo spread featuring street star Gilda Ambrosio:

My inspiration for this outfit was Gilda Ambrosio
My inspiration for this outfit was Gilda Ambrosio

In this photo, Ambrosio’s sporting the newly minted trend-of-the-month: embellished denim. It’s a fad I disliked back in 1999 when Express was trying to make sequin-cuffed flares happen. I’ll be skipping the trend again this year, due to its limited shelf life.

But I still admired Ambroisio’s flair for combining disparate wardrobe items to create a whimsical, arresting concept. Shape is very important — the over-sized coat, the generous jean sizing, the exaggerated blousing of the tee, the high-high turquoise heel.

Shoes: Prada (Saks Off Fifth Outlet)
Shoes: Prada (Saks Off Fifth Outlet)

My own version doesn’t look a whole lot like Ambrosio’s — the jeans (last seen here) are plainer, the coat (last seen here) is slimmer, the white tee (last seen here) has less fabric to work with, the shoes are about 500x more blingy. But whenever I am inspired by another woman’s outfit, I’m really trying to approximate her exact look. Instead, I’m trying to echo a feeling — super-casual spiked with sophistication.

What street style stars do you admire? I’d love to hear about your favorites!

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