Ariel Winter Slays in Skintight White Dress and Gray Over-the-Knee Boots for a Confident Night Out

Ariel Winter has long been open about her decision to undergo breast reduction surgery, a choice she made to feel more comfortable in her own body.

The “Modern Family” star continues to embrace her confidence and celebrate her curves, making bold fashion choices that reflect her unapologetic self-expression.

Ariel Winter rocks a skintight white dress with gray over-the-knee boots, a slung black leather jacket, and a bold red bag, showcasing her effortless night-out style

Ariel Winter Stuns in a Skintight White Dress and Gray Over-the-Knee Boots in West Hollywood

In February 2017, Ariel was spotted in West Hollywood wearing a stunning figure-hugging dress that showcased her glamorous style.

Reflecting on the judgments she often faces, Ariel once said, “I think people make a lot of judgments about me based on what I wear and all the things that I do.” With this in mind, her bold outfit and undeniable confidence send a powerful message about embracing self-love and defying societal expectations. She effortlessly turned heads that night, proving that true style comes from confidence within.

The then-19-year-old actress and singer wore a skintight white dress from Are You Am I. The dress featured a square neckline, a dangerously high hemline, and was completed with ribbed detailing and silicone piping.

Ariel Winter arrives at Catch seafood restaurant in West Hollywood, California, on February 23, 2017 (Credit: WENN)

Finishing the Look: Ariel Winter Adds a Pop of Color and Chic Accessories

Ariel styled her figure-hugging frock with a touch of rocker edge, draping a black leather jacket over one shoulder for an undone, effortless vibe. She added a burst of color with a bold red leather bag adorned with a playful pom-pom charm — a statement accessory that lightened the sleek, monochrome palette.

Grounding the look, the actress slipped into faded gray over-the-knee boots set on chunky heels, blending comfort with a confident silhouette. A swipe of pink lipstick, pale blush nails, and a gleaming silver choker completed the ensemble, striking the perfect balance between bold and polished.

Ariel Winter showcases her back tattoo while styling a figure-hugging white dress paired with gray over-the-knee boots and a bold red bag featuring a pom-pom charm

How to Style Over-The-Knee Boots for Any Occasion

Over-the-knee boots are a versatile addition to any wardrobe, offering both style and functionality. For a chic, preppy look, consider pairing them with a plaid sweater mini-dress, as demonstrated by Nicky Hilton. This combination not only keeps you warm but also adds a touch of sophistication.

Alternatively, for a more relaxed vibe, Olivia Palermo showcases how over-the-knee boots can complement a poncho, blending elegance with modern flair. To explore more styling ideas and see how other celebrities wear over-the-knee boots, check out our comprehensive guide on thigh-high boots outfits.

Ariel Winter steps out in chic gray suede over-the-knee boots featuring a sleek, slouchy design and chunky heels, perfect for elevating any night-out look

From Red Carpet Glam to Casual Cool: Ariel Winter’s Evolving Shoe Style

Over the years, Ariel Winter has balanced daring red-carpet choices with effortlessly chic off-duty looks — all anchored by her signature confidence and love for statement footwear. Whether stepping out in thigh-high boots, strappy wedges, or minimalist sandals, she continues to showcase a fearless approach to fashion that celebrates individuality and body positivity.