Vintage clothing is one of the easiest ways to build a wardrobe that actually feels like you. The colors are more interesting, the prints are more fun, the construction is often better, and there is something inherently satisfying about wearing a piece that has already had an entire life before it landed in your closet.

There is, however, one tiny problem. Vintage looks can be tricky because they can go from super cool to costumey REAL quick. 

Let’s set the scene. The dress is from the 1960s, the shoes are from the 1960s, the bag feels like the 1960s, your hair is doing a 1960s thing, and suddenly you are no longer a woman going to dinner on a Thursday night, you are an extremely committed extra in a period film.

Of course, there is nothing wrong with going full vintage if that is your thing, but if you are trying to incorporate older pieces into an everyday wardrobe, the trick is usually not to make the entire outfit historically accurate. It is to balance the beauty of the past with small pieces of now.

A 1960s floral mini dress can feel very different depending on whether you pair it with a matching vintage handbag and kitten heels or throw it on with a sneaker and a simple pair of earrings. The dress has not changed at all, but the context around it has. That is really what we are doing when we modernize vintage: changing the context.

So if you have something sitting in your closet that you desperately want to wear but always end up taking off, start here. These are five of my favorite ways to bring vintage pieces into the present without losing what made them interesting in the first place.

1. Let Your Bag Change the Entire Mood

Bags are probably the easiest way to shift the decade an outfit seems to belong to.

One of my favorite tricks is using a bag that is slightly more decorative than the clothing around it.

For example, if you have something from the 1990s that feels a little grungy, oversized, or almost frumpy when you put it on, adding a beaded evening-style bag completely changes the energy.

This is where something like the Gatsby Bag or the After Hours Bag from The Edit becomes incredibly useful. A chunky beaded bag against worn denim, an old leather jacket, a slip skirt, or a loose vintage dress creates this perfect little tension between casual and polished. Suddenly the piece that felt tired feels intentional.

If the clothing is simple, reach for an interesting bag. If the outfit is already doing a lot, try grabbing a simple leather bag (no frills) and watch the look transform. You are not trying to make every single piece of the outfit compete for attention.

2. Use Shoes to Modernize Your Best Vintage Pieces

Shoes are a big deal because they establish the entire mood of an outfit.

A vintage midi skirt with a delicate pump reads one way. The same skirt with a loafer reads another way. Put it with a giant platform boot and suddenly we are having an entirely different conversation.

Honestly, I will always recommend having a good pair of loafers somewhere in your closet. They are nearly impossible to date because versions of them have existed across decades, and they can calm down even the loudest vintage piece. Put loafers with a bright 1970s dress, a pleated wool skirt, wide-leg trousers, or an old printed blouse and suddenly the outfit feels grounded instead of themed. No one will question your look at the office. 

But you can also go completely in the opposite direction, which I also recommend.

Sometimes the best thing you can do for a sensible vintage piece is give it a loud shoe. Take an old wool skirt. Maybe it is beautifully made, the fabric is incredible, the length is perfect, but every time you wear it you feel like you are heading to work 9 to 5 for Franklin Hart Jr.. 

Do not give up on the skirt; think bigger. Step outside of your comfort zone in the Sunbeam Platform Boots. That pale yellow platform against a traditional wool, tweed, or plaid immediately pulls the outfit out of whatever decade it came from and puts you on the streets of Manhattan in 2026. (Seriously, who is she?)

The Blush Foldover Boots do the same thing in a completely different way. They are soft, sculptural, pale pink, and just strange enough to make a quiet wool skirt feel exciting again.

That is often all it takes. You do not have to match the era. Some of the best outfits come from letting decades completely crash into each other.

3. Add One Piece of Jewelry That Makes Everything Else Feel Intentional

Funky pins and jewelry are always a good idea, particularly when the rest of the outfit needs a little personality.

I have always loved pins because they are very low commitment. You can put one on a cardigan, a blazer lapel, the pocket of a denim jacket, a scarf, or even a bag, and immediately make the outfit feel more like you.

We’ve all been there: you found the perfect vintage house dress, the shoes are right - it all feels so chic. Then you grab a cardigan because it is cold, and the cardigan suddenly makes the whole thing feel a little too Home on the Range. Imagine if you had a tiny brass ice cream cone to put on it, or an embroidered motif that was a little edgy? She’s back!

The same idea applies to jewelry, which remains one of my favorite wardrobe cheat codes.

I particularly love a good bangle because you can wear one with jeans and a T-shirt and instantly look more finished without looking like you tried very hard. One thin bangle feels clean and minimal and two or three feel more styled - without taking over the look. Mixing widths, colors, and materials here is strongly encouraged. There is absolutely no rule saying that your gold jewelry cannot sit next to silver, acrylic, resin, wood, or something you found in your grandmother’s jewelry box.

Vintage wardrobes already tend to contain jewelry collected from different places and different decades, and I personally think it looks better when you lean into that instead of trying to make every piece perfectly coordinate.

The goal is making it look like you have been collecting cool sh*t your entire life.

4. Throw Something Unexpected Over It

Outerwear has an enormous amount of power over the way an outfit reads because it is often the largest visual piece you are wearing - and what people see first.

If you have a vintage dress that feels too sweet, a coat can toughen it up. If you have a slip dress that feels too bare, a dramatic jacket gives it structure. 

That’s one of the reasons why I chose the Marty Coat for The Edit this fall. A zebra coat is exactly the kind of piece that makes an older wardrobe feel current because it has existed in different forms for decades without ever really belonging to a single one of them. It can feel 1960s, 1980s, 1990s, or completely contemporary depending on what you put underneath it.

The coat does not erase the vintage element; it reframes it. Your grandmother’s skirt can absolutely hang out with a zebra coat, and I encourage it.

5. Remember That Your Hair and Makeup Are Accessories Too

This is probably the most overlooked part of styling an outfit.

We spend so much time thinking about what to wear with it that we forget there is another enormous visual element - our hair and makeup.

Hair changes proportion, hair changes neckline, hair changes how much visual weight is happening around your face and shoulders. And sometimes the reason an outfit feels wrong has absolutely nothing to do with the clothing.

If you are wearing a high-neck vintage blouse, turtleneck, dramatic collar, or something with a lot of fabric happening around your shoulders, try pulling your hair back. A ponytail, bun, clip, headband, or simply tucking your hair behind your ears can open the entire outfit up. If you have vintage hairpins or clips sitting somewhere in a drawer, this is your cue to start experimenting with them again.

On the opposite end, if you are wearing something with a deep V-neck, an open neckline, spaghetti straps, or a simple tank-style silhouette, letting your hair down can add exactly the visual weight the outfit needs. Big curls, waves, long hair, and volume let the hair become part of the styling.

And then there is makeup, and you really do not need much of it. Lipstick might genuinely be one of the fastest ways to update a vintage look. I love a true red with vintage because it is timeless enough to make sense but graphic enough to feel deliberate. Bright pink can do the same thing (see above). A modern berry, deep wine, or even purple can completely change a floral dress that would otherwise feel very literal.

Sometimes one modern beauty decision can anchor the whole outfit in the present.

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The point of owning vintage is not to recreate the exact outfit someone wore fifty years ago. In fact, I’d like to encourage you to stop thinking of your closet as “vintage” vs “modern”, these pieces are all just yours. You chose these things at some point because they looked like a part of your personality that you wanted to let shine. 

Sometimes you just need a little inspiration, and I hope you found some here.

So pull out that vintage dress you have not worn in two years, try the wool skirt again, dig the funky blouse out of the back of the closet, and start playing dress-up again. The coolest thing you can do with a vintage piece is make it look like it has always belonged to you. <3