What to Wear in 50 Degree Weather: Chic Layering and Trendy Transitional Outfits

Layering is the name of the game in 50-degree weather – it’s that tricky territory where you crave cozy comfort but also want to look polished and current. This season, mastering those in-between temperatures is an invitation to show off savvy layering, clever outfit combos, and on-trend silhouettes that make transitional dressing anything but boring.​

Effortless Transitional Layers:The Must-Have Formula

On brisk, 50-degree days, it’s all about mixing cool-weather staples and statement layers, with a nod to this year’s runway colors and textures. Start with a breathable base, like a fitted cotton tee or long sleeve, and top with an oversized scarf, a chunky knit, or a trending cropped jacket. Visualize baggy vintage denim or relaxed trousers paired with structured outerwear, a light trench, or a suede bomber, both runway favorites for Fall 2025. Riding boots keep it fashion-forward and practical, while satin ballet flats add a pop of sophistication. 

The finishing touches? Style with an on-trend crossbody bag and oversized sunglasses for a city-ready look.​

Eight Layered Looks to Try Now

Switch up your rotation with these outfit ideas, each drawing fresh inspiration from style editors and the streets of Paris and NYC:

Light trench coat layered over a ribbed knit midi dress and heeled boots, classic yet polished.​

High-waisted baggy jeans, crisp white tee, and an oversized scarf, finished with leather boots.​

Cropped bomber, crewneck sweater, pleated skirt, and sneaks for sporty chic vibes.​

Overshirt or shacket worn with straight-leg trousers and a fitted turtleneck—simple yet on trend.​

Relaxed trousers, boxy sweater, cropped denim jacket, and ballet flats for downtown cool.

​Layer a fleece hoodie under a puffer vest, complete with wide-leg joggers and chunky sneakers.​

Button-down shirt, wide trousers, and lightweight duster paired with loafers for daytime chic.​

Shorts with leggings, a knit vest, and a tailored blazer for that playful nod to street style.​

When These Looks Work (and Don’t)

Layered ensembles shine for just about any body type if you pay attention to proportions. Petite wearers might opt for cropped jackets or shorter scarves to avoid feeling swamped, while tall figures can play up wide-leg trousers and long knits. Be wary of excess bulk: thin, quality fabrics layer best. Slightly chilly? Add a smart base like cashmere or merino. If the afternoon turns warm, peel a layer and show off the style underneath.​

Which Look Are You Trying Next?

The right mix of layers can turn cool-weather blues into pure style joy. This season, invest in one stand-out outer layer and experiment with combos until you land one that radiates your personal vibe. Which look are you excited to try on your next crisp morning stroll?

Your 50 Degree Wardrobe Questions, Answered

What shoes should I wear in 50 degree weather?
Trendy options like riding boots, chunky sneakers, ballet flats, or leather loafers all work—pick based on forecast and outfit mood.​

Can I wear skirts or shorts at 50 degrees?
Absolutely layer with tights, boots, or even leggings underneath for warmth. Top the look with a smart jacket or chunky knit for balance.