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ClassyTrendy · June 3, 2025

15 Fashion Items That Will Remind You of Shopping at Sears in the ’80s

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Shopping at Sears in the 1980s was more than a chore; it was a cultural experience. The catalogs were thick, the fitting rooms were always busy, and the fashion was unforgettable. Whether you were buying clothes for school, holidays, or just because you begged your parents enough, Sears had it all. These 15 looks bring back the textures, colors, and styles that defined an ‘80s childhood. Let’s rewind to the good old days of shoulder pads and Velcro shoes.

Table of Contents

  • 1. Pastel Windbreakers
  • 2. Acid-Wash Jeans
  • 3. Velcro Sneakers
  • 4. Graphic Sweatshirts
  • 5. Denim Overalls
  • 6. Turtlenecks with Bold Prints
  • 7. Corduroy Pants
  • 8. Leg Warmers
  • 9. Colorblock Jackets
  • 10. Polo Shirts with Striped Collars
  • 11. High-Waisted Shorts
  • 12. Knit Sweater Vests
  • 13. Ruffled Blouses
  • 14. Tracksuits
  • 15. Jelly Shoes

1. Pastel Windbreakers

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Lightweight and shiny, pastel windbreakers were a staple of the Sears kids’ section. They came in candy-colored hues like mint green, peach, and lavender. The elastic cuffs and zip-up front made them practical for chilly mornings. Many had fun with geometric patterns or color-block designs. You wore them to school, to the mall, and on every family outing.

2. Acid-Wash Jeans

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These iconic jeans looked like they were splashed with bleach and attitude. Sears sold them in every cut imaginable, from slim-fit to baggy, with high waists and tight ankles. They paired perfectly with a tucked-in tee and high-top sneakers. The wild texture made every outfit stand out. Even parents gave in and bought a pair eventually.

3. Velcro Sneakers

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Before laces were cool, Velcro sneakers ruled the playground. Sears stocked them in flashy colors, often with lightning bolts or cartoon characters on the sides. The satisfying rip of the straps became a daily sound in classrooms. They were easy, fun, and totally ’80s. Every kid had a favorite pair and maybe even a backup pair for gym class.

4. Graphic Sweatshirts

Eleanor Jane/Pexels

Sears sweatshirts were a canvas for ‘80s pop culture. Whether it was a sparkly unicorn, a “Totally Rad” slogan, or your favourite Saturday morning cartoon, it was there. They were soft, slightly oversized, and ideal for layering over jeans or leggings. Some were even fuzzy on the inside for extra comfort. These were worn until they practically disintegrated.

5. Denim Overalls

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Denim overalls were the go-to outfit for kids who loved comfort and style. Sears offered them in light, medium, and dark washes, often with colorful stitching or patches. Worn with one strap undone or over a striped turtleneck, they had attitude. The front pouch was perfect for hiding candy or toys. These were built to survive both recess and road trips.

6. Turtlenecks with Bold Prints

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Turtlenecks were more than just a warm layer, they were a fashion statement. Sears carried them in bright stripes, polka dots, and abstract prints. They scratched a little but looked amazing under sweaters or overalls. Whether you were posing for a class photo or going to grandma’s house, these were the go-tos. Style and function met in every fold.

7. Corduroy Pants

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Corduroy pants from Sears were cozy, colorful, and slightly squeaky. They came in classic fall tones like mustard, burgundy, forest green, and tan. The textured fabric added a “grown-up” vibe to any kid’s wardrobe. Paired with polos or sweaters, they felt dressy without trying too hard. They were a staple in everyone’s dresser drawer.

8. Leg Warmers

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Thanks to movies like Flashdance, leg warmers danced off the screen and into Sears. They were sold in every shade imaginable—hot pink, electric blue, even glittery gold. Worn over leggings or jeans, they added flair to any outfit. You didn’t need to be in ballet class to rock them. Every fashion-forward kid had at least one colorful pair.

9. Colorblock Jackets

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Bold and boxy, these jackets combined primary colors in geometric panels. Think red, yellow, and royal blue divided with sharp angles. They were warm, zip-up, and sometimes even reversible. You could spot a Sears colorblock jacket from across the schoolyard. They made every kid look like a walking work of ‘80s art.

10. Polo Shirts with Striped Collars

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Polo shirts at Sears came with double-striped collars and tiny chest logos. They gave off a sporty, preppy vibe that parents loved and kids tolerated. Tucked into khakis or worn loose with jean shorts, they worked for any occasion. They were perfect for school picture day or family get-togethers. Clean, simple, and unmistakably ‘80s.

11. High-Waisted Shorts

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These shorts sat high on the waist with bold belts, big buttons, or paper-bag pleats. Sears sold them in denim, cotton, and pastel shades. Worn with a tucked-in tee and jelly sandals, they screamed summer. They looked especially cute with frilly socks and a ponytail. Every warm-weather wardrobe had a few pairs on rotation.

12. Knit Sweater Vests

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Sweater vests made kids look instantly more “grown-up.” Sears offered them in argyle, stripes, or soft solids like baby blue and lavender. They were layered over collared shirts or turtlenecks for picture-perfect looks. Ideal for holidays, recitals, or church, they had a charming vibe. Even if kids didn’t love them, moms definitely did.

13. Ruffled Blouses

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Fancy and frilly, ruffled blouses added instant elegance. Sears stocked them in white, pastel pink, and floral prints, often trimmed with lace. The necklines featured bows, buttons, or Peter Pan collars. These were special-occasion tops, perfect for birthdays or Easter. They made every girl feel like a mini princess.

14. Tracksuits

KoolShooters/Pexels

Matching tracksuits were the ultimate in coordinated comfort. Whether made of shiny nylon or plush velour, they were everywhere. Stripes down the sleeves and flashy logos made them sporty and fun. Sears offered them in bold jewel tones and cool two-tone combos. You wore them to school, to the mall, and to lounge around in style.

15. Jelly Shoes

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Plastic, colorful, and impossible to ignore, jelly shoes were a trend explosion. Sears sold them in clear, pink, purple, and glitter-flecked versions. They were squeaky, often uncomfortable, but completely irresistible. Paired with dresses, shorts, or even socks, they worked for any occasion. No ’80s summer was complete without them.

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.
Shop my clothing line here.

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