The Chic Way to Style a Blazer in Winter 2026

Between single- and double-breasted, fitted and oversized styles, there are many different blazers to choose from these days. The same goes for styling them—endless ways. If you’re looking for one easy outfit formula to follow, though, take inspiration from actress Whitney Peak.

While leaving The Today Show in New York City this morning, Peak was photographed in a pinstripe blazer layered over a button-down shirt and paired with faded bootcut jeans. The denim balanced the tailored formality of her upper layers, adding an effortlessly cool edge. For shoes, she chose closed-toe platform heels that grounded the ensemble.

I’m sure I’m not the only one who associates blazers with formal workwear and traditional office settings, so seeing Peak style a blazer in a completely different light feels refreshing. She intentionally ditched the conventional pairings—like matching tailored trousers and slingbacks—and took the unexpected route. This element of surprise has set cool, chic outfits apart from those that are just fine in 2026.