My Rules For Wearing Vintage, When You’re a Bit Vintage

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I love vintage clothing! Love it. (My definition of vintage, and I realize it is fluid, includes clothing and accessories from the 1970’s and earlier). For a couple of years I collected and sold vintage clothing on eBay, and became pretty knowledgeable about the defining styles of the 20th century. I have a real love affair with dresses and skirts from the 1940’s and 50’s. I adore that feminine silhouette, the emphasis on waist and hips, the graceful lengths and the drapey fabrics. I still shop at a few eBay stores that sell very nice quality vintage at good prices, including DexterDoggie, DeniseBrain, and Floozee’s Vintage.

Today I still own a few of my former beauties, like this one:

A fab 1950’s party dress that can be made to look very current

I just sold this gorgeous 1940’s bias-cut velvet gown

And every now and then I will wear a favorite fitted sheath from the 50’s, so long as I haven’t gained six ounces. I still thrill to the fine construction, the wonderful old labels and the attention to detail. I find I stand and walk with extra attention to form when I am wearing these dresses.

I don’t dress in head-to-toe vintage any more. It now feels too costume-y to me. If I wear my beloved black sheath dress, I wear modern jewelry and shoes, and I forgo a vintage style hat or gloves. That combination is a beautiful look, but at age 56, I feel like I am trying too hard. I will enjoy vintage jewelry any day of the week with my modern clothes, and a vintage leather handbag is a big yes, anytime.

Here are my not-too-hard-and-fast guidelines for wearing vintage over A Certain Age (your mileage may vary, and there are some 50+ bloggers who absolutely own head to toe vintage!):

  • When wearing vintage dresses I wear my usual modern(ish) hairstyle and makeup. No 40’s-style rag-curls or bright red lips.
  • If wearing an extreme vintage piece, like a circle skirt, I pair it with a contemporary blouse, belt and shoes. I avoid a kitten-ish sweater (a good rule for me any day) or a vintage checked blouse, for example.
  • Similarly, I’ll wear a sheer nylon vintage blouse with a current pencil or A-line skirt, a modern belt, tights and boots or booties.
  • Vintage accessories are cool any day of the week, especially necklaces and bracelets. I have a wonderful mini-collection of these and wear them often. See Debbi at She Accessorizes Well for some glorious vintage jewelry pieces.
  • I’m not a big scarf person, but vintage scarves can be gorgeous, and a true bargain in the thrifting world. Look for real silk, and interesting old labels.
  • Perfect for vintage scores: gloves, in leather, cotton or silk; and handbags of all sorts – leather, straw, velvet, embroidered, whatever strikes you. 
  • Not too many vintage shoes fit my modern feet, so I often choose modern shoes with a vintage vibe, like these:
Great with a dress: Naturalizers, via Zappos, $89.00

So cute with a casual skirt or jeans: Dirty Laundry via Zappos, $39.99 on sale

    Vintage clothing and accessories add so much fun to my wardrobe, and I love the sense of history they convey. So long as I am careful to avoid the costume look, I’ll continue to enjoy hunting down and wearing vintage. What say you?

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    10. Sounds like you're very knowledgeable in the vintage arena and the dresses are stunning.  I wear vintage frequently and have a collection that I adore.  I usually mix it up with contemporary pieces, but sometimes I combine eras.  Whatever I feel like as I put my outfit together! I also have vintage shoes, which are fun until they fall apart.  

    11. Hi Megan – I know what you mean. Some of those 50's dresses are just so darned pretty!

    12. Thanks Terri. I got interested about the time I first had an internet connection, and discovered the world of vintage clothing.  I tried to find a vintage wedding dress but couldn't get quite the right fit/style — but the hook was set  : >

    13. Thanks Amber and thanks for coming by. You could sew from some vintage patterns someday, I would like to hear from you if that is easy or difficult.

    14. That is the most wonderful way, when your vintage pieces have emotional value. Thanks so much for coming by.

    15. Oh, I'd love to see some of those pieces on you. The jeweled cashmere sweaters of the 50's are works of art. Thanks so much for coming by!

    16. Yes, I am excited to see your restored coat, Debbi. Hard to imagine cold weather right this minute, but in your part of the world, it will come soon enough!

    17. Thank you Pam. I agree, some of the dresses and suits from that era are breathtaking.

    18. You look awesome in your 50's style dress and wide belt. That's what I call owning the vintage!

    19. I had not realized you had the interest in vintage clothing.  These are some great tips.  I would love to see you model that first dress.  It is absolutely breathtaking.

    20. That first dress is stunning!  Your rules are very good! You don't want to look like you've been dressing in vintage since it wasn't LOL You want to look modern  and trendy in "new" vintage 🙂 I need to share this with my mommy!

    21. I also follow similar rules as you. I love vintage but don't want to look costume-y so I mix my vintage pieces(some that belonged to my grandmother!) with modern .

    22. Thanks for the great tips. I don't own a lot of vintage, but I usually try not to wear them too often so I get to keep them longer. You are not vintage just vintage chic! I love the vintage dress, it's fabulous!


    23. So far, I like vintage on other people, not me. Those two dresses are gorgeous. I can picture you wearing them, especially with the contemporary pairings and accessories.

    24. Thank you for your sweet comments on my blog,  I appreciate them so much. Love vintage, my Aunt when I was in my college would send me her boucle suits and tweed suits.  I wore them like a new piece I just bought from the store.  I have vintage blouses circa 1970 from my mother. I have a vintage 1950s black cashmere cardigan jeweled enclosure sweater of my mother's that I adore. Wearing vintage with modern pieces makes me feel really chic because you can add a piece from years past but still be current with what is hot now.

    25. Those are good guidelines, Patti.  Your dresses are so gorgeous!  I'm also a fan of modern shoes (with modern cushioning!) that have a vintage look.

    26. Oooo the top dress is fabulous. I think it helps if you can find things that are a bit timeless (like a black dress). Even if the dress has a really dramatic design I think those transition better than fabric colors and patterns (which tend to waver in and out of style much faster).

    27. I learned something new about you today! I did not know that you sold vintage on ebay.  The pieces you show are beautiful. I really like all your tips and thank you for mentioning me! I have some lovely vintage jewelry that I will wear this winter, it's just too heavy for summer.
      I will have to ask your opinion on how to style my vintage coat. I need to get the fur collar sewed back on it. It will be a while before it is cold enough to wear it so I do have some time yet!
      Like Pam, I would love for you to model your prized vintage dresses!

    28. Patti,
      Good tips.  I happen to be a vintage junkie myself.  You are so right about combining to many pieces into an outfit

    29. I would love to see you in that 1950s party dress…it is fabulous…I think it is wonderful that you developed this area of expertise.  The clothes can be so incredible from the 50s and 40s.  Good post!!

    30.  have had to tone my vintage dressing down a bit.  I don't want to look like I hauled the outfit our of my closet from the 50's.  Not that I wore grown up clothes in the 50's but some youngin's wouldnt know the difference!  And you are right–some people can carry it off better than others.  sometimes its just a matter of attitude.  What not to wear did a good episode on it.  I did a post on my vintage–great minds think alike.

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