Family Encyclopedia >> Beauty & Style

9 Must-Have Trendy Winter Dresses for Fall/Winter 2019/2020

The dress remains the ultimate feminine fashion staple. In summer, we effortlessly rotate through a collection of lightweight dresses for vacations or work. As the go-to for warm days and glamorous vibes, dresses dominate the scene.

But when winter arrives and temperatures drop, style often takes a backseat to cozy sweaters and pants—a missed opportunity. While pantsuits offer stylish warmth, winter dresses provide elegance, comfort, and insulation when selected thoughtfully.

Drawing from our expertise in seasonal trends, we've curated 9 essential winter dresses for your wardrobe this season.

Explore this expert selection of trendy winter 2019/2020 dresses to inspire your shopping.

Top Trendy Dress Styles for Winter

Long Dresses

This winter, long dresses dominate street style, suiting every body type and aesthetic as a season essential.

  • For a casual minimalist vibe, choose a plain long shirt dress.
  • Embrace the punk rock Fashion Week trend with animal print or patent leather versions.
  • Romantic bohemian rock fans: flowy floral dresses paired with standout accessories define your look.

Floral Print Dresses

Florals bloomed across Fashion Week runways this season, injecting color into outfits paired with rock, classic, or bohemian elements.

Opt for long fluid dresses in diverse floral prints. Style with tall boots or ankle boots, a leather jacket, or fitted blazer for effortless trendiness and sophistication.


The Blazer Dress

A winter wardrobe essential: the blazer dress. Effortlessly chic, it pairs with ankle boots, sneakers, or thigh-high boots.

For runway-worthy polish, select the tuxedo-style officer dress in classic black.


The Sweater Dress

The sweater dress reigns as a winter trendsetter—accessorize strategically for impact. Modern styling options include:

  • Sporty: Sweater dress with cutting-edge sneakers.
  • Chic: Oversized sweater dress belted at the waist with sleek over-the-knee boots.

The Shirt Dress

The shirt dress delivers timeless comfort and refinement. Winter standouts:

  • Short, flowy printed versions in autumnal hues with ankle or knee-high boots.
  • Long belted styles with retro flair, updated via modern tall boots for a fresh edge.

Discover our 6 expert tips for selecting a trendy winter shirt dress.


The Pussy-Bow Dress

In retro-chic mode, the ascot or pussy-bow collar trends strongly this season.

This elegant tie adds sophistication to preppy and neo-bourgeois aesthetics everywhere. Ideal in fluid A-line cuts.


The Wrap Dress

The wrap dress—with its flattering, heart-shaped silhouette—never fails to impress. Versatile for summer or winter styling.

Wrap dresses thrive in endless variations: wild python or tartan prints, classic florals for boho chic. Choose your perfect match.

For 2019/2020 winter trendiness, layer a long wrap with elegant tall boots.


The Glitter Dress

Shine bright this year—perfect timing for holidays! Shops brim with sequined, glitter, or rhinestone-embellished dresses.

The season's silhouette: short glitter dresses with asymmetrical necklines, evoking 80s drama with bold sleeves and volume.


The Denim Dress

Denim dresses excel in casual winter styling. Warm and comfy, elevate with tights and tall boots. Favor straight, trapeze, or fitted shapes.

Layer with chunky knits for relaxed appeal.

For lady-like elegance, try a long denim dress à la Lena Hoschek from fall/winter 2019/2020 shows.


In Conclusion:

Seeking chic inspiration for romantic nights, friend outings, or events? Our trusted recap of winter dress trends 2019/2020:

  • Long dress
  • Long floral dress
  • Blazer dress
  • Sweater dress
  • Shirt dress
  • Pussy-bow dress
  • Wrap dress
  • Glitter dress
  • Denim dress

For timeless chic, a Peter Pan collar dress offers enduring trendiness with its innocent charm.