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ClassyTrendy · June 29, 2025

8 ‘Ugly’ Fashion Trends That Are Somehow Back Again

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Fashion is cyclical, and some trends once mocked or dismissed as “ugly” are now being reclaimed by style influencers and fashion-forward dressers alike. What was once considered outdated or even tacky has found its way back onto runways and social media feeds, rebranded, reimagined, and worn with pride. Whether it’s chunky silhouettes, loud prints, or throwback accessories, these trends challenge the rules of conventional beauty and lean into bold, ironic style.

Table of Contents

  • 1. Chunky Dad Sneakers
  • 2. Jelly Sandals
  • 3. Visible Socks with Sandals
  • 4. Baggy Cargo Pants
  • 5. Sweater Vests
  • 6. Oversized Sunglasses
  • 7. Denim Maxi Skirts
  • 8. Clashing Prints

1. Chunky Dad Sneakers

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Once considered clunky and unfashionable, dad sneakers are back with a vengeance. These thick-soled, orthopedic-looking shoes, popularized by 1990s dads and overlooked gym-goers are now sported by models, celebrities, and style icons. They add an element of intentional awkwardness to any outfit, which is surprisingly refreshing in an age of hyper-curation. Often worn with dresses, wide-leg pants, or even suits, dad sneakers lend a sporty and rebellious edge.

2. Jelly Sandals

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Originally loved by kids in the ’80s and ’90s, jelly sandals were bright, plastic, and squeaky, a fashion faux pas in adult wardrobes. But they’re back, and they’re being worn with high-fashion confidence. Modern versions come with updated materials, sleeker shapes, and even designer collaborations. Their playful transparency and nostalgic vibe make them a fun, unexpected twist in minimalist summer outfits. Paired with crisp linens or breezy dresses, jellies now straddle the line between kitsch and chic.

3. Visible Socks with Sandals

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Once considered the ultimate style sin, wearing socks with sandals has become surprisingly trendy. This formerly ridiculed combo is now embraced by fashion influencers, blending comfort with a deliberate sense of quirkiness. The key lies in choosing the right textures and silhouettes, think ribbed socks with chunky Birkenstocks or sporty crews paired with platform slides. This trend is no longer just about practicality or laziness; it’s about self-expression, layering, and playfulness.

4. Baggy Cargo Pants

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Cargo pants, once ridiculed for their bulky silhouette and excessive pockets, have returned, especially in oversized or low-rise styles. Previously associated with outdoor utility or early-2000s boy bands, cargo pants are now embraced for their effortless streetwear appeal. Modern versions often feature cinched ankles, lightweight fabrics, or even satin finishes. Styled with crop tops, blazers, or bralettes, they’ve gone from tactical to trendy. The trend taps into the larger Y2K revival and a craving for comfort-meets-function.

5. Sweater Vests

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Sweater vests used to be the punchline of nerdy or “grandpa” fashion. Boxy and outdated, they were often relegated to school uniforms or holiday gatherings. But today’s sweater vests are tailored, colorful, and styled in unexpectedly cool ways. Worn over crisp shirts or solo with wide-leg pants, the new generation of sweater vests adds academic flair with modern edge. Whether cable-knit, argyle, or cropped, they lend vintage charm to casual outfits.

6. Oversized Sunglasses

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Oversized sunglasses were once ridiculed for being too gaudy or bug-eyed, but they’re now an icon of high-fashion drama. From shield-style wraparounds to huge square frames, these sunglasses dominate modern street style. The bigger, the bolder, the better. They offer instant glamour and mystery while protecting your entire upper face from the sun. Often paired with minimal outfits or head-to-toe neutrals, these shades become the focal point.

7. Denim Maxi Skirts

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Once thought of as frumpy or overly modest, denim maxi skirts have made a stylish return. These long, often stiff skirts were a mainstay of early-2000s casual wear and later dismissed as outdated. Now, designers and influencers are reimagining them in sleek silhouettes, front slits, and distressed hems. Paired with tank tops, blazers, or tall boots, the denim maxi is suddenly cool again. Its appeal lies in the blend of vintage charm and utilitarian ease.

8. Clashing Prints

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Mixing mismatched patterns used to be a major fashion don’t. Clashing florals, plaids, or animal prints were once seen as chaotic and uncoordinated. Today, intentional print-mixing is celebrated as a creative and fearless fashion move. Style pros mix stripes with florals, polka dots with abstracts, and even blend various animal prints for maximalist impact. The key is finding cohesion in color palettes or scale. This trend reflects a larger shift toward self-expression and fashion that breaks traditional rules.

Posted In: ClassyTrendy

Hello there! My name is Chi Li, 5'2", founder of PETITE DRESSING, the clothing line for women 5'4" & under. Are you petite and have you been frustrated with what to wear?
This is an issue few truly understand and even fewer brands truly address.
Being petite myself, I have been writing about fashion for short women since 2016 and my brand petitedressing.com has touched the lives of millions.
My styling concepts for petite women not only focus on the perfect fit but also on flattering & elongating the petite frame for a lean silhouette, optimizing the proportions.
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