Now & Later: Styling for Transitional Weather

· Transitional weather can make choosing an outfit feel like a chore.
· The right handbag will alleviate some of that stress by pulling your whole look together.
· Read on for key features and tips to consider when styling your bag for transitional weather.

When the forecast predicts cool mornings, warm afternoons and chilly evenings (with a chance of rain somewhere in between, of course), deciding what to wear can seem impossible. While styling for transitional weather is always a challenge, having a bag that can carry some extra clothing, remain reliable through the rain and work with a variety of wardrobes will make the process a bit easier. Most importantly, the right handbag will pull your entire look together—even if you feel like you’ve thrown on layers haphazardly, no one else will be able to tell. Below, we’ve compiled some key tips to keep in mind when styling your bag for transitional weather.

Style Tip: Wear an expandable carryall for effortless, everyday style that will hold all those extra layers.

When it’s brisk in the morning and warm in the afternoon, you might have to shed some layers throughout the day—think sweaters, vests or even hats, scarves and gloves. And given how unpredictable the forecast can be, you may even need to put them back on later. There’s nothing more frustrating than not having enough room to carry that extra clothing in your bag as the weather changes, but with an expandable carryall or tote, you won’t have to worry about whether you’re wearing too many layers or where you’re going to put them. When it’s chilly, wear your carryall over your chunky knits for a cozy vibe. When the warm weather hits, throw your sweater in your bag and show off your favorite vintage tee for a casual daytime look.

Try: Brooklyn Shoulder Bag 34, Brooklyn Shoulder Bag 39

Style Tip: Pair durable, water-resistant bags crafted of leather or canvas with everything from oversized puffer coats to lightweight tees.

Unexpected showers can really put a damper on the day, especially if you don’t have the right bag by your side. Choose a bag crafted of water-resistant materials like leather or Coated Canvas. Not only are these materials easy to clean, they also pair well with a variety of wardrobes, whether you’re still wearing your warmest hat and scarf or heading out with just a light denim jacket.

Try: Bleecker Bucket Bag, Plaza Bag In Signature Canvas

Style Tip: Team a versatile neutral bag with just about any outfit in your closet—they’re always in style.

From winter whites to spring pastels, a versatile neutral bag will go with all your different seasonal looks, acting as a complementary plus-one for all sorts of occasions. Luckily, today’s neutrals are anything but boring (think hues like olive, chalk, maple and more). Whether you’re still wearing dark, cozy winter sweaters or you’re slowly transitioning to a brighter spring color palette, a versatile neutral bag will complement any style or mood.

Try: Soft Tabby Shoulder Bag In Maple, Soft Empire Carryall Bag 40 In Olive

Published: February 2026