Looking back over my old photos, nothing dates them more specifically than the jeans — except for maybe the hair. Blown out layers and loose fit 501s? 1996. Barrel curls and low cut Seven flares? 2001. Air dried hair and Madewell skinny legs? 2010. But at some point in the last decade, the denim game changed in a big way.

No longer is there only one acceptable current silhouette. Instead, we’re met with a dizzying display of options when it comes to denim. While there’s more freedom than ever when it comes to style and fit (yes!), it can be downright overwhelming to choose a direction when it comes to investing in a new pair of jeans.

I’ve broken down 5 of my favorite fits below, along with a few buying guidelines to help you along. So what jeans are really in style now, at the turn of the decade? The answer to the old question is finally a modern one: Whichever jeans you feel great in. Now scroll down to find your perfect pair.

featured image by hannah haston

Loose Fit 501s

“Boyfriend jeans,” “loose fit”, “mom jeans”… whatever you want to call them, the classic 501 silhouette is (finally!) back and it’s still universally flattering. Not to mention comfortable. These are my jeans for life, and I love them so much. Personally, I really believe in the Levi’s brand, especially for classic denim. Everything else is derivative. My advice for keeping this fit feeling super current: make sure to pair it with a delicate shoe (either sandals, mules, or a heel.)

High Waisted Flares from Mother

I love this silhouette — it’s so sexy, so seventies, and so right now. Mother does high waisted flares very well, and this pair would look great with a slick ankle boot or wedge heel. I love the trouser pocket. To keep this style feeling current, make sure not to hide the waistline under a blouse. Show it off by tucking in a gausy blouse, or pairing them with a cute crop top.

High Rise Skinny Jeans from Madewell

Madewell is a great option for affordable stretchy denim that’s cut really well. These high rise skinny jeans can feel really classic when paired with a tee and sneakers, or very edgy when tucked into an over-the-knee boot. The stretch makes them the comfortable jeans you’ll reach for over and over again.

Wedgie Fit Levi’s

They’re don’t get high marks in the comfort category, but Levi’s new “wedgie fit” jeans look real, real good from behind. They’re reminiscent of the 501, but much tighter in the inseam, thighs, and waist. Again, you don’t want to hide the waistline with these. Pair them with a simple tank, a fitted sweater, and a pair of white sneakers for a simple Parisian style of cool.

DL1961 x Marianna Hewitt Hepburn High Waist Crop Leg Jeans

So this is a really fun pair that calls it’s influence straight out — Katharine Hepburn. The combination of a 90s wash, non-stretch denim and totally 40s silhouette makes the jeans thoroughly modern. Pair them with a silk blouse and velvet slippers for super chic look.

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