Wearing a denim vest in the depths of winter is quite unexpected and exactly the kind of styling moment that separates the effortlessly chic from the merely practical. This time of year, wardrobes tend to skew toward the predictable so the denim vest offers a fresh take. This season, I’ve managed to take it from rugged to refined to help break up the heavy layers with a few pointers along the way…

don’t skimp on your layers

The key to pulling off a denim vest in winter is all in the layers beneath it. Rather than defaulting to layering over a simple cotton crewneck, explore unexpected pieces in finer materials that bring sophistication and warmth. Even a turtleneck worn under the vest and anchored with a cinched trench coat creates a visually compelling, cold-weather ensemble. When layered thoughtfully, the vest becomes a quiet anchor that ties the entire look together. I recently opted for a more striking look with a crisp white button-up with an exaggerated sleeve. The dramatic shape adds movement, contrast, and a sculptural element that elevates the vest far beyond its casual roots. A soft cashmere or merino wool knit are also options in deep winter tones to introduce texture and contract. The goal is to create a luxe backdrop that allows the vest to become the exclamation point rather than the entire statement.

Choose the Right Denim

Surprise, surprise. The tone of the denim itself actually matters. In winter, I always opt for darker rinses. They feel more refined and pair seamlessly with wool, leather, and heavy outerwear. I also lean more toward clean cuts with minimal distressing. In this case, it made the vest appear more seasonally appropriate and less like a summer leftover. The right denim character ensured the vest held its own alongside more structured garments.

Play with your Proportions

A denim vest is naturally structured, which opens the door for compelling proportion play. Winter is the perfect season to lean into some drama. Given my shorter frame, I opted for a vest in an oversized silhouette to lengthen my torso and paired it with a wide-leg trousers for an editorial silhouette. Another option? An A-line midi skirt styled with tall leather boots leans into a romantic, 1970s-inspired mood. When working with proportions, the rule is simple: if the vest is boxy, keep the base layers slim; if the vest is fitted, allow your other pieces to add volume.

Bring in some Unexpected Outerwear

For obvious reasons, the denim vest should not serve as your outermost layer for fall/winter; but it really thrives when it becomes the layer before the layer. I styled it underneath a structured houndstooth blazer to achieve a high-low contrast that felt pulled together directly from the Ralph Lauren East Coast prep playbook. You can also slip it under a sweeping wool overcoat for a menswear-meets-street-style effect or let it peek out from beneath a longline puffer to break up the visual monotony of super technical fabrics. As a mid-layer, the denim vest gives subtle dimension and a nice little element of surprise where it’s least expected.