Raiding the retro closet: 5 vintage looks that never go out of style, IMHO

Looking through old pictures of my family I can see the lineage of style that preceded me. My father’s side of the family lived in rural Minnesota, and my grandmother’s wardrobe reflected her environment. But that didn’t stop her from wearing incredible jumpsuits and headwraps, or floral button-ups and high waisted trousers I would do anything to have now. On the other side of the family, my mom’s mom’s style was very glamorous and she favored garments like velvet fringe tasseled a-line dresses and roller-curled hair with deep purple lipstick. The women in my family may not have had much money, but they were never, ever underdressed.

These women knew how to dress themselves. They knew how to dress themselves better than I will ever know how to dress myself. Which is why I’ve always been baffled by the “dressing like a grandma” jab. What’s so wrong with dressing like a grandma, exactly? Women, especially older women, tend to get policed by society on what they wear and are constantly told to “dress their age.” Double standards and unfairness and sexism aside —there is no such thing as “dressing your age.” Dress how you feel, more like. And if what you feel is more old-timey and found in your grandma’s wardrobe, then you do YOU.

Here are five styles we can learn from, thanks to the generations that came before us.

1. Turtlenecks

Audrey Hepburn made turtle necks look cool, svelte and glamorous. And our grandma’s took note. I prefer very simple and basic turtlenecks, Target is a great place to look for no frills turtlenecks under $20. Whether it’s tucked in to a wool midi skirt in fall, or paired with slim fitting denim, the turtleneck suits all.

2. Simple Lingerie

Modern lingerie can be confusing. There are so many straps! Underwires! Frills! Our grandmothers knew how to wear a simple, sexy slip under their outfit. I love this halter lace vintage slip in my shop right now, the pattern is sleek and feminine. Slips are secret double agents in that they can be worn underneath dresses and skirts, and also on their own as nightgowns or lounging around the house attire. Their simple lace busts and flowing silky skirts offer a breezy and sophisticated solution to panty lines and lazy Sunday mornings.

3. Belts with everything

I am a belt fanatic. I belt every outfit I wear. Especially after watching my waistline triple during pregnancy, the belt felt increasingly wonderful with each outfit. Our grandmas wore belts with every dress, skirt and pair of pants. I say the bigger the better, but more modest belts can be just as wonderful. Etsy is a great place to search for vintage belts that will add thoughtfulness to your everyday dress. Careful not to try too hard to match your belt with the rest of your outfit. A statement belt is a wonderful way to make your outfit more authentic and adventurous.

4. Cardigans

I’ve got so many cardigans that my husband has started raising an eyebrow anytime we are out and I am eyeing a shiny new one. I love them because they are just magical —they’re absolutely wonderful for all seasons. They make freezing movie theaters more cozy, shield the windy summer evenings and glam up a downplayed outfit. Of course I’m drawn to loud cardigans that boast pom poms and fringe, but simple can be lovely, too. The great part is their versatility — they can be worn year-round with a multitude of outfits. While they’re on the pricier side, Anthropologie has incredible statement cardigans every season, like this glorious hunter green swan knit cardigan (for the more adventurous and wild dresser) or their Huanako Poncho (which I am placing all my bets on for my birthday in two weeks…please universe, please don’t fail me).

5. Head wraps & scarves

I am one of those folks who went through a three year period of dying my hair way, way too often. My hair turned into brittle needles of hay and needed some major TLC. I swore off all heating tools and deep conditioned the heck outta my locks for almost a year. During that time, headwraps made their way into my life, and I’ve never looked back. They’re bossy, beautiful, and vibrant. New to tying wraps? Check out Youtube tutorials, like this one. You can use vintage scarves, new head scarves or really anything that remotely resembles a band of fabric you can wrap and twist around your head.

The inspiration is endless when we look back in time. Take notice, scrap what doesn’t feel “you” and borrow what does. The past is full of wonderfully gorgeous styles to learn from.


Follow my vintage shop adventures & other styling obsessions on Instagram @talltumbleweedvintage

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