Best Winter Outfits In 2025 With Midi Skirts

FALL/AUTUMNStyle is a way to say who you are without having to speak.”

• Cozy Weather Outfit

• Layered Look Outfit

• Transitional Dressing

• Weekend Brunch Outfit

Cozy Weather Outfit

Elevate your sweater dress ensemble by cinching it with a chic belt to accentuate your waist and add flair to your look.

• Opt for a statement belt with bold buckles.

• Try a slim belt for a more understated look.

• Experiment with different belt colors to contrast or complement your dress.

• Choose a metallic belt for a touch of glamour

Layered Look Outfit

Enhance your sweater dress outfit by layering it with a trendy denim jacket for a casual yet stylish look. The denim jacket adds a touch of edge and modernity to your ensemble.

Transitional Dressing

This winter outfit looks both elegant and warm. The woman is wearing a light grey turtleneck sweater as a cozy base layer. On top, she has a stylish grey herringbone-patterned overcoat, which adds both warmth and a touch of class. She’s left the coat open to show off a classic black and white plaid midi skirt with grey accents, which is great for colder weather. The skirt is paired with black tights for extra warmth. To finish the look, she’s wearing shiny black ankle boots, perfect for winter days.

Weekend Brunch Outfit

Outfit 1: Denim dresses are such universal pieces! I’ve never seen anyone who doesn’t look good in one. Try out this distressed denim button-down dress whose fringed hem gives off an effortless feel. Add an open-front knit coat cardigan for texture and finish off the look with backless horsebit mules to drive home the on-the-go vibe.

Outfit 2: If you want to take it up a notch, I’d opt for a striped half-zip pullover sweater and pair that with Levi’s shaping skinny jeans to highlight your silhouette. Layer on a double-breasted belted long trench coat as it makes anything look more sophisticated. For shoes, try out some white leather sneakers for an unexpected pairing that creates a cohesive relaxed vibe. 

Outfit 3: This final look leans more preppy. Partner a crisp white long-sleeve button-down poplin shirt with a knitted sweater vest and straight-cut jeans. This combination is a classic and easy trick to make it seem like you spent hours styling your look. Finish it off with backless loafer slides and a chevron-quilted shoulder bag.

Style is a way to say who you are without having to speak.”