How to Buy Through the Decades: A Stylist’s Guide to Shopping Vintage & Contemporary
Fashion is cyclical, but great style is timeless. Shopping secondhand gives you the chance to step into different eras of design, discover quality that can’t be replicated, and curate a wardrobe that feels both intentional and one-of-a-kind. Whether you’re drawn to the elegance of the 1920s, the bold silhouettes of the 1980s, or the playful experimentation of Y2K, knowing what to look for can help you shop with both confidence and clarity. Below, we’ll walk through the decades of womenswear. From the Roaring Twenties through Y2K, and also share tips for buying contemporary secondhand.
The key is knowing what’s authentic, what’s collectible, and what translates best into a contemporary wardrobe.
The 1920s: Glamour & Modernity
It has now been a full century since true 1920s garments were produced, which makes them incredibly rare and often regarded more as collectibles than everyday wear. Think geometric Art Deco motifs, metallic embroidery, and feathered or fringed details that embodied the spirit of modernity. The ‘20s dramatically broke from the corseted formality of previous decades, setting the stage for fashion’s future embrace of ease and movement. The style of the decade was about liberation in dress: shorter hemlines, straight silhouettes, and decorative beading.
What to look for: Drop waists, silk slips, fringe details, geometric jewelry, and cloche hats.
Fabric focus: Silk chiffon and metallic-thread embroidery.
Value cue: Original flapper dresses with intact beadwork are highly collectible, though extremely fragile. Surviving pieces, especially beaded evening dresses or coats with Art Deco embellishments are highly sought after by collectors and museums alike.
Tip: Due to true 1920s pieces are rare and fragile, look for inspired reproductions from the 1970s or 1980s when designers revived Deco style. They are more common and usually in better condition than the originals, making them more wearable, but still rooted in history.
The 1930s: Streamlined Elegance
Also noted as the Depression-era. The 1930s emphasized elegance through resourcefulness due to restrictions of the time. Fashion was defined by elegance and fluidity; bias-cut dresses skimmed the body, creating long, graceful lines that emphasized natural curves. Silhouettes were softer and more elongated than the styles of the 1920s, with details like flutter sleeves, draped necklines, and floor-length hems adding a sense of understated glamour.
What to look for: Gowns with cowl necklines, flutter sleeves, velvet evening coats. Also check closures! Side snaps and metal zippers (plastic wasn’t common yet) can help confirm authenticity.
Fabric focus: Silk satin, rayon crepe, and velvet.
Value cue: Dresses cut on the bias in excellent condition are rare finds. Many were handmade or couture-level, making them investment pieces at the time and have since soared in value if well preserved.
Tip: Prioritize condition. Rayon and silk from this decade are delicate, so check for shattering (especially in silks) and weak seams. Often the best places to seek garments that have been stored with care are estate sales, auction houses, and specialized vintage retailers.
The 1940s: Utility Meets Glamour
World War II shaped style with rationing and practicality. For the first time trousers truly became a common garment for women. We saw the everyday woman wearing suits, structured shoulders, and high-waist trousers, while men’s military surplus influenced daily wear.
What to look for: Tailored blazers, tea length dresses, wide-leg trousers, and utility jackets.
Fabric focus: Wool gabardine, rayon, cotton blends. During the war, natural fibers like cotton, wool, and silk were rationed and redirected to uniforms, parachutes, and military needs. This drove innovation in synthetic fibers like nylon and rayon.
Value cue: WWII-era utility dresses and structured jackets carry historical and fashion value. Men’s military surplus; bomber jackets, military issued wool sweaters, and field coats also have an androgenous appeal.
Tip: Authentic WWII-era surplus is highly sought after, both for its durability and its influence on modern fashion. Look for M-41 or M-43 field jackets, wool pea coats, navy deck jackets, flight jackets, and high-waist wool trousers. Authentic pieces will often have stamped or sewn-in military labels with contract numbers and dates. CONDITION. DOES. MATTER. Wool moth holes and rusted hardware are common, so prioritize well-preserved examples or pieces with repairable wear. Due to originals being rare, later military-issue garments from the 1950s–1960s can also be excellent alternatives, carrying the same timeless design at a more accessible price.
The 1950s: The Postwar Hourglass & Everyday Glamour
When WWII ended, so did fabric rationing. With men returning from war, women were encouraged to embrace domestic roles again. This cultural shift was reflected in fashion: soft, feminine silhouettes replaced wartime pragmatism. Specifically, Christian Dior’s 1947 “New Look” featuring rounded shoulders, a cinched waists, and full skirt set the tone for the following decade. The style celebrated abundance after years of scarcity. Clothes were designed to highlight the hourglass shape, reinforcing femininity and domestic ideals. At the same time, the rise of suburbia and consumer culture meant women were expected to look polished not just for occasions, but for everyday life.
Cultural icons began to redefine what femininity looked like. Marilyn Monroe assisted in ushering in wiggle dresses, pencil skirts, and body-conscious tailoring as glamorous, yet acceptable everyday wear. Grace Kelly embodied understated elegance and preppy refinement. While Audrey Hepburn popularized slim trousers and ballet flats, offering a chic alternative to full skirts. Together, these women broadened the definition of 1950s femininity.
What to look for: Circle skirts, swing coats, shirtwaist dresses, mid-century structured handbags, and letterman jackets/sweaters.
Fabric focus: With rationing over, cottons and polished wools dominated. Early synthetics like nylon and acetate became common for everyday wear (wrinkle-resistant, easy-wash fabrics had large appeal). Laminated fabrics and permanent pleats emerged as novelty innovations.
Value cue: Designer labels like Dior, Balenciaga, or designer couture are museum-worthy. Everyday cotton shirtwaists with novelty prints are accessible yet still collectible. Letterman jackets and sweaters from well-known universities or with distinctive chenille patches also command high prices on the secondhand market.
Tip: Do authenticity checks. True 1950s varsity pieces will often have chain-stitch embroidery, wool body construction, talon zippers, and chenille patches sewn directly onto the garment (rather than glued or mass-produced appliqués you see in later reproductions). The weight of wool and leather also tends to be heavier than modern versions.
The 1960s: Mod & Counterculture
The 1960s marked a break from the structured femininity of the ’50s. Fashion split between two poles: the sharp, geometric minimalism of the mod look and the free-spirited, bohemian styles of counterculture. Social change fueled style. The rise of the “modern woman,” youth-driven consumer power, and cultural revolution all demanded clothes that expressed freedom and rebellion. Hemlines rose dramatically, colors popped, and prints turned bold as individuality became the new uniform.
What to look for: Bold printed shift dresses, go-go boots, boxy vinyl purses, A-line coats in bright colors, and suede fringe jackets.
Fabric focus: Synthetics became mainstream; polyester, acrylic, nylon, and PVC are prized for being wrinkle-resistant and affordable. Wool knits and silks were still used, but they require careful handling today.
Value Cue: Emilio Pucci was the master of bold, swirling prints in saturated colors. His designs became synonymous with the fashion focus and jet-set lifestyle of the 1960s, worn by everyone from Sophia Loren to Jackie Kennedy. A 1960s Pucci silk jersey dress in good condition can easily command $1,000–$3,000+ today. Even modest separates have a reliable resale market because of the print recognition.
Tip: If you’re new to shopping vintage Pucci, start with scarves. They’re easier to find, often more affordable, and still carry strong resale demand.
The 1970s: Eclectic & Expressive
The 1970s were about freedom and fluidity in lifestyle, politics, and fashion. After the turbulence of the 1960s, people experimented with identity through clothes. Style became less about following a single “look” and more about mixing and expressing. This is why the decade feels so eclectic: earthy bohemian one day, glittering disco the next. A few key notes:
The women’s movement pushed boundaries of what women could wear. For the first time we see everything from pantsuits to plunging necklines.
Disco culture brought sequins, lamé, and glamorous evening wear, while folk and rock scenes kept bohemian styles alive.
The world feels more accessible. We see global influences in peasant blouses, caftans, and embroidery reflected a growing interest in non-Western dress and artisan traditions.
What to look for: High-waist flares, suede vests, wrap dresses, metallic lamé.
Fabric focus: Denim, suede, leather, lamé, jersey knits, polyester blends, and natural cottons. Suede and denim dominated the casual side, while synthetics and lamé ruled disco nights.
Value cue: Vintage Levi’s (“Big E” tab on back pocket, pre-1971), suede jackets, designer wrap dresses. These hold solid resale and are wearable entry points.
Tip: Always check denim details! Levi’s with a red “Big E” tab, single-stitch hems, or paper patches are especially collectible. For suede or leather, condition is key: avoid major signs of damage, but light wear can add vintage character.
The 1980s: Bold & Power-Driven
The 1980s were the decade of affluence, ambition, and image. Style became a form of armor in an era driven by corporate culture, pop celebrities, and global consumerism. Clothes were unapologetically bold, designed to make a statement and project power. The decade of excess gave us oversized silhouettes, power suits, and statement accessories. Think shoulder pads, bold prints, and saturated glamour.
What to look for: Blazers with strong shoulders, leather minis, oversized denim jackets, and bold costume jewelry.
Fabric focus: Bold colorway synthetics, sequins, lamé, leather, metallic knits. Lycra and stretch fabrics also became mainstream with the fitness craze.
Value cue: Designer ’80s clothing is highly collectible, thanks to sculptural tailoring. Vintage designer and costume jewelry from this decade also hold steady resale value.
Tip: The ’80s market is still abundant. Nike, Adidas, and early designer collaborations from the decade are increasingly sought after. Original ’80s rock shirts are also another booming collectable category.
The 1990s: Minimalism & Edge
The 1990s broke from the bold excess of the ’80s, and welcomed a new kind of cool: casual minimalism and effortless edge. This was the decade where “airport style” thanks to supermodels and celebrities became a thing, with celebrities like Kate Moss, Carolyn Bessette-Kennedy, Naomi Campbell, and Gwyneth Paltrow turning jeans, white tees, and tiny sunglasses into aspirational uniforms. Fashion shifted towards quiet luxury and lived-in authenticity, whether through stripped-back minimalism or grunge rebellion. Think slip dresses, crop tops, and tailored denim alongside oversized flannels and combat boots.
What to look for: Vintage Levi’s 501s, silk slip dresses, leather jackets, band tees, and Doc Marten boots.
Fabric focus: Silk, denim, leather, cotton basics. When the cultural mood shifted toward minimalism and authenticity in the 1990s, natural fibers felt more honest, pared-back, and luxurious.
Value cue: Levi’s 501s, slip dresses, vintage flannels, Doc Martens are accessible, easy to style, and have steady resale demand. Prada nylon, Helmut Lang tailoring, and early Calvin Klein minimalism are prized. Original Supreme, Stüssy, and ’90s Nike or Adidas pieces that are also now coveted by collectors, blurring the lines between vintage fashion and sneaker culture.
Tip: The ’90s is one of the most wearable and beginner-friendly decades to thrift. Look for everyday minimalism pieces slip dresses, denim, leather jackets that remain timeless staples in modern wardrobes. Small details like “Made in USA” tags on Levi’s or original Prada triangle logos can dramatically increase resale value. Designer ’90s (Prada, Helmut Lang, Calvin Klein) have also surged in collectability keep an eye out for labels.
Y2K: Playful & Futuristic
After a decade of clean lines and subtlety, consumers were ready for flash and experimentation. The new millennium felt like a reset button, and fashion embraced a playful optimism that mirrored the cultural mood. The early 2000s marked a radical break from the stripped-back minimalism of the ’90s. Instead of quiet tailoring and neutral palettes, Y2K style was about play, experimentation, and excess. Fashion leaned into logos, shine, and daring silhouettes, often with a tongue-in-cheek graphics to solidify a sense of fun. The low-rise jean exploded for the first time as a reaction against high-rise ’90s denim now dubbed the “mom jean”. Youth culture celebrated a bare midsection aesthetic, with crop tops, baby tees, and rhinestone belts a hyper-sexy but casual look that defined the era.
What to look for: Juicy Couture tracksuits, designer logo bags, baby tees with graphics, and low-rise designer denim (True Religion, 7 For All Mankind, and Rock & Republic).
Fabric focus: For the first time, elastic fibers were woven into jeans. This gave rise to ultra-low-rise, body-hugging denim. The stretch made daring cuts wearable and fueled the denim boom. We also saw the rise of performance wear. Companies like Nike and Adidas were experimenting with Dri-FIT, ClimaCool, and other moisture-wicking fabrics. These technologies trickled into mainstream wardrobes, paving the way for athleisure.
Value cue: Designer logo bags from Dior, Louis Vuitton, and Fendi are cornerstone Y2K collectibles. More mainstream: Juicy tracksuits, stretch denim, rhinestone-embellished tees are more plentiful, hold nostalgia value, and are fun to wear.
Tip: When buying Y2K secondhand, always test stretch fabrics many elastics degrade over time. Jeans that sag, leggings that have lost shape, or velour that’s flattened won’t hold their value. Prioritize pieces where the elasticity and texture are still intact.
Contemporary Secondhand: 2000s–Now
Welcome to the resurgence of luxury investment pieces, making contemporary secondhand shopping a smart way to curate quality, style, and value. Buying contemporary secondhand is about curating what’s current while skipping retail markups. You can find nearly new designer, garments made of premium materials you would prefer not to buy new due to their cost, and everything in between.
What to look for: Timeless staples (blazers, denim, boots), pieces with lasting quality, and current-season items resold at a fraction of retail.
Fabric focus: Wool, silk, cashmere and merino knits, real leather (bags, shoes, jackets), high-quality organic cotton, and technical fabrics with longevity.
Value cue: Buying contemporary secondhand is about strategy. Invest in designer pieces (The Row, Phoebe-era Celine, Chanel) that hold resale value. Everyday pieces should be chosen for quality and longevity, not trend alone.
Tip: Focus on construction and fabric. A well-made contemporary wool coat or leather bag will outlast multiple fast-fashion purchases. Organic fabrics like organic cotton, linen, hemp, and Tencel are grown and processed with sustainable methods, which naturally drives up their retail price. Buying these pieces secondhand allows you to access high-quality, eco-friendly garments at a fraction of the cost, making it both stylish and budget-conscious.
Buying through the decades is about collecting pieces of history, expressing individuality, and choosing fashion that lasts. The best wardrobes are built with both permanence and personality. True vintage tells a story that is sometimes collectible and other times simple wearable nostalgic magic. Contemporary secondhand lets you buy far more quality without having the pricetag. Together, they form a style language that resists fast turnover and celebrates fashion as art, history, and self-expression.
Happy hunting.
Jessica Conrad Walsh
Founder, Conrad Campbell
