How To Take Your Vintage Dresses to New Heights

Aug 25, 2015


Vintage dresses usually fall into two schools of thought: 1) You think of Doris-Day-like figures in gingham dresses canning jam and college girls in berets bent over cups of cappuccinos, discussing Proust, or 2) you think frump.

You're either romantic or frumpy, but in either category you have no idea what to do with the piece. If you haven't had a chance to dabble in vintage yet and allow yourself some trial and error, then the whole thing can seem intimidating. Some girls can pull it off but I'm just not one of them, you think. It's pretty, but just doesn't fit your style.

Want me to prove you wrong? Keep reading.


It's all about having a few vintage styling tricks handy. You need to know what to slick down and what to modernize to not feel like you're wearing an estate sale costume, and I've found that the easiest way to do that is to focus on one thing: Accessories.

It's really as simple as that. Take this look for example. This full number has the potential to be overwhelmingly feminine, but I gave it a quieter voice by matching it against modern, minimalist pieces. For shoes I went with something on-trend and chose two-strap sandals, and continued to pull the look through to the twenty-first century by pairing it with a simple circle purse and sunglasses in a trendy shape. To tone down the girliness factor I swept my hair up and slicked on some dark, vampy lipstick and called it a success.

Now to imagine how you yourself could style a piece like this, have yourself walk through the possibilities: 

  • What sort of shoes can you contrast against something so sweet and feminine? How about clunky sandals, pointed lace up flats, gladiator sandals, white sneakers? Try to stick to shoes that not only add a fun contrast against the dress, but are also on-trend styling wise to give it a more obvious modern twist.
  • What kind of bag would make this piece feel more modern? Maybe a small leather backback, a clean-lined cross-body bag, or maybe something with some personality like a fringe purse? This way you're either trying to subdue the flamboyancy of the dress (by pairing it with simple, unassuming bags) or you're trying to give it a playful juxtaposition by clashing it with something a little more loud (like a fringe bag or something with pattern or color).
  • How else can you make this dress feel more you and more on-trend? Think of what's both popular and timeless right now. Are you known to wear a few dangly necklaces? Do you like to stack rings on your fingers? Love colored aviators? Baseball caps?

By taking some time to figure out the answers to these questions, you can just about make any vintage dress feel not only more modern, but more like you.

how-to-style-vintage-this-summer how-to-style-summer-dresses-this-season

For more inspiration, here are some other vintage inspired looks. Study them and think about why they work: (ONE| TWO| THREE| FOUR)

How To Take Your Vintage Dresses to New Heights 

 Let's discuss: What's been the most game changing vintage styling tip you've learned?

Want more vintage styling tips? Continue reading:

outfit details
Dress: thrifted
Sandals: Gap
Sunglasses: Thailand

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  1. Gorgeous photos! It makes me want to go back to Paris and buy some cheap 10Euro vintage dresses from this shop i found - I didn't buy any because I told myself I didn't need more clothing. But y'know, Now I regret it!

  2. You totally nailed this look! Dress, lip color, purse - everything is on point! In love with the first pic..

  3. YES, you've totally given this dress a modern, paired down and fresh look. Love it! Hope you're having a splendid day, gorgeous!! xo

  4. Such good points for people wanting to modernize vintage! I love how you always find really fresh ways to wear garments. Personally, I'm totally okay with looking like I'm from another era, but y'know. It's just me!
    That lipstick is killer.

  5. Yessssss, it's all about the shoes! This is helpful :)

  6. Wow, that dress is so lovely! I love the neutral color, and the length is quite stunning, too.

    Always love that dark lip on you!

  7. I am often at a loss at how to style vintages clothes! I love how you styled this, definitely very summery and breezy!

  8. You know what? I am actually one of those women who has always felt frumpy in vintage dresses. When I manage to find something vintage that fits I feel like a kid who is playing dress up at Grandma's. However, after reading these tips, I'm kinda wanting to give it a try again. Maybe mix in some boots and a floppy hat and call it a day. In this case, I really do think it's the sandals that changed everything. I realllllly need to get a pair of sandals eventually.

  9. this is such a gorgeous dress, and you've made it look so contemporary. I really really really wish St. Louis had better vintage clothing stores--- I miss getting my vintage fixes!

  10. I never would have thought of shoes as a way to modernize a vintage dress...which, you know, now that you've pointed it out seems like something I should start doing ASAP.

    And, as always, you ooze cool in your outfit! ;)

  11. I actually feel a bit concerned for people who feel like they can't bring vintage into the modern world. Fashion is so cyclical, you see a 50s or 60s influence on the runways off and on every few years. Great tips for those just getting into vintage, though, it's amazing what a difference a few accessories can make.
    Love the dress, very sweet and comfortable for summer!
    Zella Maybe

  12. I just love this! Vintage dresses are my absolute favorite. <3

  13. This dress looks fabulous on you and there is no way you could look frumpy in that! But I also immediately noticed your chic lipstick and sunglasses - super on point. Overall amazing and way better than the other examples at the bottom.


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