How to Style Baggy Pants (And Not Look Sloppy)
What Are We Wearing?
If you’ve scrolled through Instagram lately or strolled down Newbury Street, you’ve seen it: baggy pants are everywhere. From slouchy denim to wide-leg trousers and relaxed cargo silhouettes, this 90s-inspired trend has officially evolved into a modern wardrobe essential. But how do you wear the baggy pant trend without looking sloppy? With the right balance of structure, proportion, and fit, you can make this trend feel elevated, intentional, and incredibly flattering. Here are three unique, stylist-approved ways to style baggy pants this season that feel current, chic and cool.
Look 1: The Tailored Contrast
My favorite version of this trend is the contrast of baggy and tailoring pieces coming together. A baggy pair of trousers styled with a fitted sweater and finished with sleek shoes creates a balanced look that feels elegant and intentional. The fitted top sharpens the oversized bottom, creating a clean, elongated line that works on every body type.
Tara’s Style Edit:
If you’re petite, choose a trouser with a front crease or center seam, making your legs look miles long.
Look 2: The Off-Duty Cool
A casual take on the cool girl look is to style a pair of baggy jeans with a cropped jacket or blazer and a clean-line sneaker or pump, depending on your plans. This look leans into streetwear-inspired ease without slipping into sloppy territory, just add one tailored element like a polished belt or button down shirt.
Tara’s Style Edit:
To avoid visual heaviness, style a shiny patent leather belt and a fitted tee, turtleneck or button down shirt to balance the weight of the denim while elevating an otherwise casual look.
Look 3: Elevated For Evening
Baggy doesn’t have to mean daytime casual. Styling satin or silky wide-leg pants with refined textures like cashmere, merino wool or twill instantly make the look evening-ready and chic. Or you can opt for satin baggy pants with a body-skimming top or bodysuit and statement heels for a show stopping moment.
Tara’s Style Edit:
Choose satin pants with a slightly thicker waistband to keep the silhouette structured and prevent the “pajama pants” look.
