Decades of Style: How to Wear Vintage Now

What’s full of history, but ready for its next chapter? If you guessed vintage clothes, you’d be 100% correct. Our first-of-its-kind digital Vintage Pop-up has arrived! What does that mean? Over 20,000 handpicked vintage and vintage-inspired pieces are ready to go the distance in your closet—think vintage dresses, leather jackets, tops, denim, and more. These pieces have lived many lives through the decades and are ready to live on in yours.

This curation is a celebration of timeless fashion as a bridge between generations—where style heirlooms transcend trends. It’s not just about wearing vintage items; it’s about carrying their stories and quality forward. By highlighting these threads of the past, we’re making secondhand fashion an intentional, rewarding choice for generations to come. These pieces have lasted because they were made to. Unlike fast fashion, quality clothing endures. We cherish good quality because clothes built to last stay OUT of the landfill and IN your closet. 

What is vintage exactly?

A quick search would show you that the term “vintage” dates back to the 15th century and has its origins in the world of winemaking. It wasn’t until the 20th century that it became associated with clothing, as interest in secondhand fashion grew between the 1960s and 1980s. Vintage clothing refers to items that are at least 20 years old—thoughtfully sourced for their enduring design, quality craftsmanship, and cultural relevance. These are styles that have stood the test of time, offering a one-of-a-kind look that feels just as current today as it did back then. With subtle signs of wear and character, each piece tells its own story—and invites you to continue it.

Read on for the inside scoop on how to style these timeless pieces seamlessly with what you already own.

How to Style Vintage Denim 

How you style your vintage denim depends on the fit, of course. Pair vintage wide-leg jeans with a cropped T-shirt for a laid-back, everyday look. High-waisted styles work especially well here, as they balance out the shorter hem. Add white sneakers to keep the vibe cool and easy, or dress it up a bit with loafers. Avoid oversized T-shirts, which can make the outfit feel shapeless, and steer clear of low-rise jeans that may throw off your proportions.

For a more polished outfit, style your vintage straight-leg jeans with a tailored blazer. The jacket adds structure to the denim’s relaxed fit, creating a chic, put-together look. A tucked-in fitted top or blouse underneath complements the blazer nicely, and a pair of heels will help elongate your legs.

For a fun weekend look, try a fitted, textured top—like a crocheted shirt or velvet cropped tee—paired with slim jeans. Finish the outfit with funky sneakers or platforms for a perfect festival-ready or picnic vibe. Prefer something more laid-back? Opt for chunky sandals to keep it casual and comfortable.

For a bohemian-inspired outfit, reach for a flowy, printed blouse and pair it with flared jeans. This combo creates a relaxed, breezy aesthetic that's ideal for casual hangouts or outdoor gatherings. Complete the look with heeled boots and a wide-brimmed hat to channel true boho flair.

Dress Outfitting 101 

Slip dresses

Slip dresses are a close competitor for the little black dress, providing endless versatility. Dress them up with a graceful clutch bag and heels, or style them more casually with a leather jacket and boots.

Maxi dresses

When you want a more covered-up look (or just more flowy fabric to enjoy), long dresses are an excellent choice. Wear maxi dresses with delicate jewelry, a designer bag, and an updo for a more upscale outing. For footwear, reach for metallic sandals, with or without a heel. 

Midi dresses

Midi dresses may be the most versatile party dress, suitable for office parties, summer get-togethers, and even formal galas. For a complete ensemble, wear midi dresses with kitten-heel sandals and gold hoop earrings. A wristlet purse in a contrasting color like gold also looks great. Wear this dress to an afternoon or evening wedding with block heels and statement earrings. Swap the heels for flats if the ceremony and reception are more casual. 

Mini dresses

A mini dress is go-to party wear for celebratory events like dances and cocktail parties. They’re a comfortable, breezy option for daytime and destination weddings. Its lightweight fabric creates a flattering, billowy silhouette and helps you stay cool in warm climates. 

Mix Patterns Like a Pro

Pattern mixing is one of the easiest ways to make vintage feel modern—and totally you. The secret sauce? Balance. Start with one standout print (like a bold floral or classic stripe), then layer in a second pattern that shares a similar color or tone. Think polka dots and plaid, leopard and stripes, or gingham and florals. Play around with the scale (like large patterns with smaller ones) and don’t be afraid to ground the look with a solid piece to keep things cohesive. Still unsure? Try a printed scarf or bag first to dip your toe in. Vintage loves a little contrast.

Have outfit ideas of your own? Follow us on Instagram or share your vintage faves with us in the comments below.

‍