STYLE // Fall Style Study

4 Tips for Styling Vintage Items

November 7, 2017

I love styling. It’s a big drive behind this blog, and it brings me great joy to build and analyze outfits. Forever a student of personal style, I like to study it and share a little bit about what I learn along the way. I’ve mentioned many times that I love contrast when building my outfits. I like to mix casual and dressy, masculine and feminine, and perhaps my favorite combo: modern and vintage (or vintage-inspired).

I have a strong affinity for vintage. It’s kitschy but chic. It’s unique but brings feelings of nostalgia. Often the pieces are high quality and stand out in an age of ‘fast-food’ clothing.

While many vintage items are beautiful and bring a sense of depth to an outfit, they are not always easy to style. If I’m not careful, I’ll look like I walked off the set of Stranger Things, or worse, That 70’s Show. I love the costuming on shows like these, but the clothing is just that – costumes. Not exactly the look I’m going for on a day-to-day basis. I want to be unique, but uniquely me. 

When it comes to wearing vintage clothing, I have learned what works for me (and what doesn’t).

4 Tips for Styling Vintage Items in Everyday Outfits

1 – Balance the number of vintage items with the number of modern items in a given outfit. In other words, too many vintage pieces in one look can make you look more ‘throwback’ than you’re going for. That’s exactly what happens when I wear my vintage denim, and vintage-esque clogs and sherpa jacket. I feel like I might be hanging out at the pool hall in Dazed and Confused. Instead, I’ll opt for 1-2 vintage(y) items per outfit, and round out the look with other items from my closet.

2 – Contrast vintage with complementary modern shapes. The vintage items I often love are detail-driven and more intricate pieces, a tooled leather bag, a cable knit sweater, or jeans worn in so well they are a roadmap of blue shades. To let these items receive the attention they deserve I like to choose modern pieces from my closet to go with them. Long, clean lines are often the perfect backdrop or complement. Classic items (like a turtleneck or a button up) work well with vintage too. They can be neutral in terms of ‘era’ and play off a vintage item well.

3 – Customize it to make it yours. It took me way too long in life to figure this out. Often vintage items won’t be a perfect fit off the rack. No big deal, drop $15 at a good tailor, and take the item from decent to amazing. When I  recently bought a second pair of vintage jeans off Etsy, I realized they were bigger in the waist/hips than I wanted. I went to an alterations place downtown. Five days and $15 later they were exactly what I was looking for. If you’re going to do this, just remember to build it into your budget when shopping vintage.

4 – Go with your instinct. I am a big fan of wearing what makes me feel good, and often that’s dictated by instinct. I try to trust my gut judgement on outfits without over thinking it too much. Pull items you love, like your favorite cashmere sweater and pair it with your beat-up vintage jeans. Or grab that amazing vintage coat you have, and pair it over the simplest dark, skinny jeans and chelsea boots. Let your instincts guide the ‘vibe’ of your look. Often they will do a great job!

Do you wear vintage items? I’d love to hear what ‘rule of thumb’ you follow for styling your decades-old favorites.

OUTFIT DETAILS: Wool Duster Vest, c/o Only Child | Vintage Levi’s, Etsy | Merino Turtleneck, Goodwill (similar in cotton) | Clogs, No. 6 Store | Saddle Bag, Cuyana

This post contains affiliate links. All photographs by Kiara Rose.


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  • Lindsey November 7, 2017 at 7:22 am

    Hey Andrea, you look great! I’ve been meaning to ask you – what tailor do you recommend in PDX? I’m looking for a good one to take in a few waists on pants, among other things. Thanks!

    • Andrea November 8, 2017 at 12:53 pm

      Hi Lindsey! I got to DZ alterations on SW Morrison. They replaced the zipper on a jacket of mine a few years ago, and that’s where I took my Levi’s to have them taken in in the back. And they are inexpensive as well. The only problem is parking is a pain. (I usually do the smart park by Target.)

  • Leah November 7, 2017 at 7:56 am

    I think remembering that vintage is about having fun is my top tip. I have been getting into vintage hats because they’re just so kooky and unabashedly “costumey.” Worn with minimalist basics, they add a lot of interest. I also love vintage dresses and skirts. The prints and shapes are so creative.

    • Andrea November 8, 2017 at 12:55 pm

      Yes, that is such a great tip. I agree, minimalist basics can be the perfect way to showcase a bold vintage item. Clothes are meant to be fun! And I love the idea of owning and wearing an item that already has its own story. It’s kind of weird, but sometimes I like to imagine who wore it before me, what their life was like.

  • Anne November 7, 2017 at 9:15 am

    I had to give myself a no-spend November challenge until Small Business Saturday (good timing too bc my car just needed new tires and now is making an asthma-attack noise under the hood…) BUT I am still looking at the consignment store for a jean jacket!

    • Andrea November 8, 2017 at 12:56 pm

      I love consignment shopping, it takes patience, but can payoff handsomely. I hope you find just what you’re looking for (after the month winds down, of course!).

  • ThatGirl November 7, 2017 at 9:34 am

    This is so timely! I bought some vintage Levi’s last week and I’m really struggling with what shoes to pair them with. I’ve got boots, but I usually want to go super casual on the weekends. I guess I should re-invest in some Chuck Taylors or something…

    • Andrea November 8, 2017 at 12:57 pm

      Have you done a try-on with all the other shoes you own? Tip: don’t do it when you’re trying to head out the door to leave, spend some down time figuring out what works. You’ve gotta ‘on board’ these vintage jeans into your closet, and part of that means a learning curve. What other shoes do you have?

  • Helena November 10, 2017 at 9:33 am

    Nice look! How do you like the duster vest? Is it very thick/varm or will it be good for both fall and winter? I’ve been looking for one for a while now. Love the Clyde vest by EZ but more looking for a wool version. This looks promising! 😊

  • Kaci December 4, 2017 at 8:22 am

    My vintage tends towards old ladies lunching so the goal is always to pair one piece with more casual young looking items to make a playful statement rather than head to toe look. My husband calls it Boho Blanche, lol.

    • Andrea December 4, 2017 at 1:08 pm

      HAHA, love it!! What a great name. He sounds pretty genius about style.