How To Dress Vintage Without Looking Outdated

Vintage dressing is one of the easiest ways to express your theatrical side, whether you’re breathing new life into mid-century separates, or going full Regency in the style (or a la mode) of our Bridgerton girl crush, Kate Sharma. A fully thrifted outfit isn’t for everyone, though, and one of the main concerns people have about styling vintage clothing is looking outdated. So, how do you dress vintage without looking like you’re wearing a costume? Here are our tips:

Pick your era

Narrowing down your favourite eras for fashion is a great starting point when it comes to vintage dressing. Think about what it is from that time you’d like to add to your wardrobe. The silhouettes? The patterns? The colours? Current trends you love are a great place to start with this — after all, rapid trend cycles mean that most popular garments are reinterpretations of styles from the past. Each decade has its own signature aesthetics that it’s known for:

  • 1920s: Flapper glamour, complete with feathers, furs, and sparkly embellishments.
  • 1930s: Structured dresses, animal print coats and the rise of the A-line silhouette.
  • 1940s: Ruffles, skirt suits and cardi-blouse-skirt combos inspired by school uniforms.
  • 1950s: Patterned wrap dresses, high-waisted everything and skirts both figure-hugging and voluminous.
  • 1960s: Mod style, miniskirts, knee-high boots and loose tailoring.
  • 1970s: Classic hippie and punk aesthetics, plus jumpsuits, disco flares, and button down dresses. 
  • 1980s: Bold colours, bolder patterns, and even bolder silhouettes. Power suits and glam-rock, chunky jewellery and neon athletic gear.
  • 1990s: Logo-laden streetwear, baggy trousers, dungarees, plaid skirts and grunge. 

  • Identify any style icons you’d like to emulate, too: off-duty supermodels of the ‘90s, ‘80s pop legends or ‘70s Hollywood stars.


    Start with the basics

    It may seem like stating the obvious, but the easiest vintage clothes to style are basics. Building up a core collection of versatile staples means you can easily incorporate thrifted styles into modern looks, and if you prefer things more minimal, it’ll allow you to build your whole outfit around one standout hero piece. On-trend outerwear essentials like trench coats and blazers are widely available in vintage shops, and they’re almost always of better quality than their modern fast-fashion counterparts. Likewise with denim jeans — you can often find discontinued silhouettes from the ‘80s and ‘90s for the fraction of the price of new pairs. Staples are a great way to subtly evoke an era, too, rather than dressing head-to-toe in decade-appropriate clothing; channel 1950s greasers with a leather jacket, or elegant Edwardian ladies with a frilly white blouse. 


    Make the clothing yours

    When you make a vintage purchase, there are plenty of modifications you can make to put your own spin on it. Take anything that doesn’t quite fit right to a tailor, who can alter it to your measurements and even completely modernise the silhouette, if you’d like. Make repairs to any wear and tear, and remove any outdated or broken embellishments — these can really age your looks. There’s a fine line to tread, though. Don’t aim for perfection; fashion in the early and mid-20th century was known for its polished aesthetic, so appearing too put-together could also look old-fashioned. Upcycle, rework, and break the rules, but make sure you keep the character that makes thrifted finds so unique.   


    Mix and match

    Experimentation is key. There’s nothing wrong with committing to a full, authentic retro outfit, but if it’s a more modern take on vintage dressing that you’re aiming for, then mixing and matching is essential. Pair older pieces with brand-new styles, blend decades, contrast casualwear with formalwear. Decades like the ‘50s, 60’s and ‘80s were a riot of loud colours, bold patterns and dramatic silhouettes — tone down clothing from these eras by styling it with denim. A faux-fur coat or cape thrown over a dress instantly adds a vintage-inspired touch to your date night looks. ‘90s athletic sweats go with pretty much every modern trouser or skirt silhouette you can think of. Get creative!


    Hair, make-up and accessories

    There are two ways you can go with your hair, makeup and accessories: minimal and modern, or vintage-inspired. The trick is to create a bit of contrast with your outfit. Try pairing a bias cut skirt with Doc Martens, white trainers or chunky sandals for a modern twist on 1930s styling, or style a dramatic ‘50s circle skirt with simple hair and natural makeup. You could do the opposite, too — antique jewellery instantly adds a vintage vibe to contemporary dresses, suiting and even casual weekend looks. And if you’re really committed, a retro-inspired haircut, like Farrah Fawcett’s signature shag cut or the ever-divisive mullet, will make even the most modern of looks feel like a throwback.

    Got the urge to go thrifting now? Check out our sister brand Trendlistr to find your next vintage clothing gem.