How to Match Vintage Outfits

December 9th, 2011
how to match vintage clothing

how to match vintage clothing



Hi Sammy!

I love your YouTube videos soooo much! But I can’t seem to pull off wearing vintage like you can! I want to, but everytime I try I end up looking like I’m wearing a costume.

How can I match vintage outfits? What are some of your tips?

Any advice you can give is appreciated!!

Thank you!



Hey Sarah!

Thank you so much for this question! I think that a lot of ladies are thinking your exact thoughts when it comes to wearing vintage! You are definitely not alone and shouldn’t feel frustrated that you’re uncertain how best to match vintage outfits.

Finding your own unique style with vintage clothing doesn’t have to be a chore. It should be nothing short of FUN! The reason I gravitated to wearing vintage at such a young age (I was about 15 when I first shopped vintage!) was because it gave me the opportunity to wear what truly spoke to my heart in the moment.

Rather than look at the pages of a magazine or what was on the mannequin at the store for my fashion inspiration, I was happily forced to simply wear what I wanted to without regard to trends!

But that’s not to say that trends don’t matter — because they definitely should be taken into account when matching vintage outfits. Unless you are aiming for a “vintage look,” the trick to matching vintage outfits is finding the pieces that are able to be integrated into your pre-existing modern wardrobe.

When it comes to matching vintage outfits so that you feel AND look good, there are a few tried and true tips that I’ve picked up over my years of trial & error and lots and lots of experimentation! Choose which tips make best sense to you, and let your creative imagination play, discover and enjoy!

Keep reading to learn how I match vintage outfits with accessories, high-waisted pants, pleated skirts and blazers. I’ll also dish on matching vintage outfits by pattern (my example: polka dots!). Plus, why simply wearing a vintage dress is the easiest way to rock vintage fashion!


how to match vintage clothing


One of the easiest ways to match vintage outfits is not to focus on the clothing at all — but on the exciting opportunities of wearing vintage accessories.

A lot of girls call themselves “bag girls” or “shoe girls” or “pearl girls.” Perhaps you are one of these girls with your modern pieces: You can’t get enough of hobo bags and own 10 of them, or you collect more pearls than Coco Chanel ever owned in her lifetime!

Whatever your accessory obsession is (scarves? rings? sunglasses?) take that love affair and translate it to vintage!


So how do you match vintage accessories to your outfit? Easy! Vintage accessories are undoubtedly the most reproduced inventory in the vintage world. What does that mean? When a store like Forever 21, H&M or Urban Outfitters need inspiration for their own accessories collections, they turn to the trends of the past.

This is why you saw a revival of the John Lennon granny circular lens glasses last summer. No one was directly attributing the trend to when they first became popular in Lennon’s ’60s days, but you bet designers were inspired by how the member of the Fab Four was wear them in his day.


When matching your outfit to vintage accessories, incorporate a purse, sunglasses, belt, jewelry, etc. into your look the same way you would with any modern pieces. The mantra “less is more” is usually your safest bet.

In the pictures above and below, I’m wearing a vintage dress, ankle booties and denim jacket with vintage accessories. I’ve opted for cat eye sunglasses, a lucite bag chain purse, a tooled leather belt with metal hardware and a bakelite bracelet.

Notice that while each vintage accessory is unique (bakelite and lucite are two very historical materials!), they are not too loud in color, design or size. I could have opted for a huge leather backpack from the ’70s for the look to give it more rugged edge, but I wanted to style this outfit with ladylike accessories that were practical for the everyday.

Want to see more pictures of gorgeous vintage accessories that you can match to your modern outfit? Check out my post on vintage designer accessories at FROCK!

how to match vintage clothing



how to match vintage clothing


You don’t have to wear an entirely vintage outfit to integrate vintage style into your wardrobe. In fact, I discourage vintage newbies from even trying to go 100 percent vintage. I even have difficulty looking good in head-to-toe vintage. Oftentimes I will wear 2-3 vintage pieces like a top, blazer and accessory or some variation thereof that is mixed with remaining modern pieces recently purchased in stores.

To successfully match vintage outfits, start off with wearing one piece of vintage only! In the photos above and below I’m wearing ONE piece of vintage in each look. Can you guess which piece is vintage and which are from modern trend stores Topshop (above) and H&M (below)?

Caught ya! I bet you are having a difficult time identifying which pieces are vintage and which are new. That’s because by wearing only one piece of vintage, the entire outfit looks brand new! If I had integrated a few more pieces into the outfit you may have been more easily able to spot them.


To look and feel awesome wearing vintage, always mix one vintage piece with modern pieces in your wardrobe. I aim to wear a vintage piece that is similarly styled to other modern pieces or becomes the “main focus” of the outfit that is surrounded by complementary modern apparel.

If I have a casual vintage piece — like a ’70s denim jacket from Lee or Levi’s — I will wear it over a casual babydoll dress in shades of blues with leather brown boots and a leather cross body bag.


If my vintage piece is a bit louder with a funky print — maybe an A-line skirt in a bright & bold graphic print — I’ll subdue the loudness of the piece by pairing it with a solid colored shell and basic black blazer.

My shoes can be a bit more funky (I love anything that’s strappy with a chunky heel!) and accessories limited to earrings or perhaps a necklace. I would focus my accessories up top and away from the boldness of the skirt so that they weren’t competing for attention from whomever is admiring my outfit!

If you love a vintage “wow” piece, wear it to display it proudly without overdoing it in the design, colors and structure of your outfit’s modern pieces and accessories. Let that showstopping vintage piece speak for itself by matching it with classic modern staples for a stunning wearable look.


For the photos you see of me wearing vintage with modern pieces above and below, I actually brought my vintage pieces to Topshop (photos above) and H&M (photos below) to match them to the clothing in the store and decide what ultimately to purchase for my complete look.

There is nothing wrong with buying a vintage piece and then bringing it to your favorite trendy chain store to see how you can style it with pieces in that store. Pick out a few pieces following the advice in Tip #2 and Tip #3 and bring your modern pieces and vintage one into the changing room to (and I repeat!) play, style and discover what combination of modern & vintage is most appealing to you!

how to match vintage clothing


Here’s a behind-the-scenes video on how I matched vintage with pieces from Topshop to create one-of-a-kind outfits!




how to match vintage clothing


High-waisted pants are a hot trend for fall/winter 2011, and will continue to be an attractive option for women’s trousers into the spring 2012 season, too.

High-waisted pants were first popular for women in the ’40s because when ladies’ husbands went off to war, they were left with little money to purchase their own clothing and “borrowed” their husband’s pants to wear! The style for men of the day was high-waisted, and so women naturally adopted the style, too.

Today’s high-waisted pants are made from lux materials like silk, come in bright colors like the “orange creamsicle” ones I’m shown wearing above, and ideally are also made with an inner-lining to protect the pants from skin residue like sweat.

Matching vintage pieces with high-waisted pants is a trendy idea for anyone to match vintage outfits. You can find high-waisted pants either vintage or new. In the photos above I’m actually wearing a pair of ’80s high-waisted pants that I’ve matched with a vintage bustier and modern blazer. My necklace, shoes and hair bow are also modern and styled to — as I suggest in Tip #3 of styling vintage with modern — draw attention to the colorfully gorgeous high-waisted pants I’m wearing.


Matching vintage to new or vintage high-waisted pants is a great idea for an attractive outfit, but how should you style the outfit as a whole? I suggest that you opt for a more sophisticated look when styling vintage with high-waisted pants. By the sheer nature of wearing high-waisted trousers, you are channeling an androgynous look that should be styled for fitted tailoring that creates a boy-ish — but still sexy!! — figure.

Because your high-waisted pants create such a teeny tiny waist, wear a top that can be tucked into your pants to keep that tiny waist in full view! Do not wear anything that is too baggy or loose up top.

Then, I suggest adding a fun blazer that is designed with basic colors, like the black & white geometric print one I’m wearing above. It’s still a fun blazer though because it has fringe trim along the bottom and cuffs. Plus, it’s collarless — a trend for spring 2012, when I bet you’ll be seeing collarless blazers sold all over the stores!


My example above leans a bit toward the sophisticated AND sexy style, too, because I’m wearing a vintage bustier top which when worn in it’s original form, is technically a piece of lingerie.

This is where a bit of creativity comes into play that I’m confident you have ready to be unleashed! While I could have worn my vintage bustier top underneath another top as a technical piece of lingerie, I’ve chosen to wear it on the “outside” so that it’s revealed to the world. But, if you are feeling self-conscious showing so much skin there is always the option of pairing a bustier and high-waisted pants with a great blazer or fitted bolero shrug.

Wearing vintage lingerie as daywear is not a revolutionary idea, but for vintage newbies & lovers alike it can inspire new ideas of how to wear the pieces we find in fresh, funky ways that work for modern sophisticated style.

Perhaps you have a vintage fur shrug that in its original form was worn as an evening piece with a dress. Well, vintage fur shrugs can also be worn in place of blazers! Instead of wearing a jacket, you wear the shrug all day almost like a “shoulder” jacket. You can pin the shrug together at your chest so that it’s styled as if it were a jacket.

There are a plethora of ways to wear vintage against its original form to inspire modern usage. Try not to look at a vintage piece as “unwearable” simply because you’re “not supposed to wear it that way.”

While I’m suggesting some great “rules” to follow in this post, one of the “rules” is that there are no rules when it comes to wearing vintage!! The true rules are the ones you create for your own comfort and creativity.


how to match vintage clothing


Another great modern piece to match with vintage is a modern pleated skirt. The knee-length pleated skirt you see above is from one of my favorite modern stores Anthropologie. I love Anthro because while the pieces are new, most of them have a touch of vintage inspiration in structure, style or print. The pieces can be expensive but are worth investing in for great classic pieces that never truly go out of style — like romantic pleated skirts in a pinky peach!

When matching vintage to a pleated skirt, opt for a vintage top and vintage accessories. Pleated skirts like the one shown above are perfect for spring, so matching a short sleeve or sleeveless vintage top for this look is probably your best bet for style success.


The beauty in matching vintage with such a classic staple item like a pleated skirt is that you can use that skirt as your “base” for whatever style you are aiming for. Use the pleated skirt as your blank slate — it’s so basic that you can opt for more fun and fabulous vintage pieces to wear around it.

In my photos above, I’ve styled four distinct looks using the pleated skirt as my base: A conservative look with a basic vintage white top with slight eyelet design, a youthful look with a vintage bandeau top and vintage denim jacket, a tropical look with a floral button-up top and straw hat and an evening look with a vintage sequin top in gold & black with fringe!

So a you can see, the pleated skirt is sort of like your easel — and whatever vintage strokes you wish to paint on it is up to you!


So how do you match your vintage top to vintage accessories? Style in a similar fashion to how you would style a modern top!

Look #1 matches a vintage white top to some bolder vintage accessories — my vintage belt has some awesome hardware and I chose to wear a vintage hat in black for colorful contrast but a vintage purse in white to complement my top.

Look #2 matches a vintage denim jacket to a vintage denim bag — so perfect & cute!

Look #3 matches a tropical top to tropical accessories in complementary colors — my straw bag is bright pink to match the top, and my necklace (hard to tell in pic) is made from shells to follow the “tropical” theme. Oh — and the sun hat! Perfect for lounging on the island!

And finally, look #4 has such a showstopper — the sequin fringe top! — that I didn’t want to distract away from it with my accessories, so I opted for tiny vintage bag, simple gold bangle and earrings!


how to match vintage clothing


For my next tip on how to match vintage outfits, I wanted to focus on a staple that every working girl undoubtedly already owns: a chic blazer!

A lot of vintage newbies may think that you can’t wear vintage to work. Yes, that is absolutely true — if you don’t style it correctly! The key is to wear a “work-worthy” modern piece to complement the rest of your vintage look. Here I’m wearing a cream colored tuxedo blazer by Theory. It’s a true classic that was first introduced by Yves Saint Laurent as “Le Smoking Jacket” in the ’60s. If you don’t already own a tuxedo jacket in cream or black, I highly suggest you add one to your modern wardrobe or buy one vintage — especially if it’s YSL!


The trick to matching vintage while wearing a blazer/tuxedo jacket and styling the outfit so that it’s appropriate for work is to focus on complementary colors.

This is a more difficult task for some people, but I have some helpful hints that anyone can adapt into their styling-consciousness.

In look #1, I’ve styled the cream tuxedo jacket with a light brown vintage midi skirt and sheer vintage black top. The colors here are brown, black & cream. Note that I haven’t repeated any colors and that the colors are all classics — not bright hues or creative patterns here! Think of your outfit as a triad (three!) of color — that way you won’t go overboard for the office, but you won’t be wearing a blazer with an all-black or all-one-color look, either.

In look #2 I did pair with my tuxedo jacket with a bright vintage dress. But note that the rest of my outfit is simple and chic — black vintage purse, black modern pumps and one accessory: A vintage gold necklace.

Because the dress is a great hue of magenta, I chose remaining pieces is basics and not brights. Adding bright pink shoes may make sense in theory because they’d match the vintage dress, but that would be too many “wow” hues for the office. While look #1 mixes three colors, I want to mix a blazer with ONE bright color to create a 2-color-outfit with accessories in basic blacks.

Here’s a behind-the-scenes video on how I styled a tuxedo blazer at Mafalda Vintage!



how to match vintage clothing


One of my favorite patterns of all time are polka dots — so when musing on a vintage outfit, a great option for my personal style tastes is to focus on a vintage piece with a polka dot design!

Whether you like polka dots, stripes, paisley, ditsy floral print or another pattern is up to you! But when shopping vintage and styling a vintage outfit, musing on what pattern speaks to your fashion heart is a great way to be certain that you’re going to create a vintage look you love.


Now how do you match vintage pieces to vintage piece designed with your favorite pattern, like polka dots? As you see in the photos above, I chose to style a look around a pair of vintage polka dot ankle pants. Instead of adding additional colors to the look though, I chose to pull the hues in the polka dot pattern (whites, creams and navy blue) for the rest of my outfit’s pieces.

I went with a cream-colored modern top, a navy blue vintage blazer, cream colored vintage pumps and a vintage hat in navy blue, too! The camera is vintage a well — a great accessory for any vintage look is always having a big ‘ole smile for the camera (vintage or not!), too!


Don’t be afraid to add another touch of your favorite pattern to an outfit by using an accessory or what I like to call a piece of “flair.”

I love polka dots so much that my wardrobe consists of random polka dot scarves, which I like to use creatively (remember tip #3 in matching high-waisted pants to vintage!) as bits of “flair” to my outfit.

For the look above, I took a polka dot scarf and tied it at my waist for a more tailored, fitted look. I love that the polka dots play off one another — almost like they are friends!

When wearing a vintage piece in your favorite pattern, accessorize another bit of flair into your look in the form of a fun accessory in the same pattern. This can be by way of a hair bow, a neck scarf, a pocket square, socks, tights, accessories or a scarf-turned-waist-belt like me.

Here’s a great video on thrifting polka dots for your vintage pattern styling inspiration!



how to match vintage clothing


What’s the easiest piece of clothing you can wear with the least amount of style energy necessary? Why, but a DRESS!

There’s a reason ladies of the past, present and future have, are and always will love wearing dresses: With the right fit for your figure, they are super flattering not to mention functional and fun. All you need to do is put the dress on, add shoes and a bag and you are ready to go!

Especially in today’s day and age, dressing at the speed of light is becoming as important as having high-speed Internet. We just don’t have the time to primp like we used to — and society doesn’t expect us to, either which is why it’s acceptable to wear a dress everyday if it suits your style, tastes and fashion interests best.

The photos above show me wearing vintage dresses for every occasion under the sun. From cotton frocks for picnics and pretty spring days to working-girl frocks for the 9 to 5 to sexy sequins for cocktail parties and holiday extravaganzas, there’s a vintage dress for everyday and every woman’s fashion sensibility.


Still not sure what kind of vintage dress to wear? Remember the opportunity to seek & discover that is already at your fingertips … and in your closet!

I said to bring your vintage piece to a modern trendy store to create the best outfit mixing vintage & modern for you. But for wearing the perfect vintage dress, it’s a matter of reverse and bringing your favorite modern dress to a vintage boutique to share with the owner/sales associate to help find the best vintage equivalent for you.

What goes around comes around, and most of today’s pieces have similarly shaped silhouettes to the styles of the ’20s and later. Your favorite dress from Zara may actually be reminiscent of a ’60s A-line tea length dress. So while you own the modern piece as inspired by the ’60s trend, you can also purchase and wear the style in its original form from a vintage boutique.

Here’s a great list of my top 10 favorite New York City vintage stores. YELP is a great resource to find a vintage boutique near you — simply type in “vintage store” in the search, add your zip code and voila! You have a great list of stores to visit near you!

Review your closet and decide what your top 3 favorite dresses are — the ones you feel so fabulous that if you could, you’d have them reproduced in every color so that you’d never wear the same one twice.

Bring those top 3 favs to your boutique and ask the owner/sales associate what dresses in the store are a similar style. After receiving your “vintage wish list” of dresses, go to town and try them all on! I have a feeling you’ll be pleased so much that you may never “go new” again!

Sarah, I hope that answers your question on how to match vintage outfits for your vintage shopping & styling inspiration!

Didn’t answer your question completely? Please leave me a comment below for further clarification! And if anyone has further questions or advice please chime in by leaving a comment below!

@ your style service,

xoxo, SD

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  1. Hi Sammy,
    you’re a total doll… & I have a hankering that we would be good friends if we knew each other! I love your tips and tricks for styling vintage, and all of your outfits are eclectic, unique, and perfectly styled!


    Check out my latest vintage blog post when you get the chance:

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