How to Style Drawstring Pants (And Why I Finally Tried Them)
Drawstring pants have moved fast over the last couple of years. No longer just for loungewear, the detail now shows up on everything from jeans — mine included — to dressy evening pants. If you’ve been drawstring-curious but not sure how to style them, here are a few outfit ideas to get you started.
First, a Word on Trying Something New
But before I get to the outfits, I want to talk about why saying yes to something new — even a detail as small as a drawstring waistband — is worth doing at any stage of style evolution.
Personal style is a melding of many elements: self-expression, taste, values, budget, suitability for a lifestyle. And any—or all—of these can shift over time. It may be a seismic shift, such as retirement or moving to a totally different climate. Or it might be something more subtle, like a favorite piece feeling “off,” or being drawn to a color, style, or silhouette we might have dismissed before.
While we might crave the simplicity of a “timeless capsule” or signature style, I’ve come to believe that those don’t work for everyone, at least not without periodic tweaks here and there. Yes, I believe in building a cohesive wardrobe around foundational pieces with longevity. But keeping it feeling fresh and feeling like ourselves means honoring those “shifts” when they happen. That might mean giving certain pieces a rest, or trying something new. Case in point: drawstring pants.
They’re not to everyone’s taste, but drawstring pants can add a relaxed and nonchalant vibe to an outfit. When I first shared a pair of knit, straight-leg jeans a couple of weeks ago in my subscriber newsletter, several of you asked me for tips on how to style them.
I’ve recently added two pairs to my rotation, and have been playing with styling options. The bottom line: don’t overthink it. This style is meant to be a bit laid-back, so I avoid anything that feels too precise or fussy.
My Favorite Ways to Wear Them
Go Shorter Up Top
The first option is to go with a shorter or cropped top. You want to avoid anything that’s snug over the knot, which will result in an obvious bump. I’ve unfastened the bottom two buttons of the cardigan for ease over the knot. A cropped shirt like this one will also work.
These are the new knit denim jeans from Eileen Fisher, which I really like. They have a bit more structure than my rag & bone Miramar jeans, but are still lightweight. And that dark, even wash looks like real denim!
Try a Tuck
Another option is to do a half or full tuck with a longer top or tee. This creates some structure and definition with two slightly oversized pieces. I LOVE these cotton poplin pants, and have been wearing them almost daily during our recent heat waves. The fabric is light and crisp and doesn’t cling. The brown color is slightly darker and deeper than it looks in this photo, also available in ivory and dark chocolate brown.
Keep It Relaxed and Untucked
If you prefer not to tuck, a relaxed fit shirt works well, especially with straight, full-length drawstring pants. You can even leave the bottom couple of buttons undone and let the tie peek through.
Tuck the Tie Away
My sizes: Jacket – 4, Top – Small, Jeans – Petite Small
If you want to pair with a more fitted top that hits below the waistband, tuck the drawstring ends (untied) inside the pants — this works best if the drawstring isn’t doing the work of holding the pants up, like when there’s also an elastic waistband. 😉
That’s what I’ve come up with so far, but I’ll keep experimenting. Have you added a pair of drawstring pants to your wardrobe? If so, how do you style them?
👉 Have a style question? Let me know in comments below.
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