how to winterize your retro wardrobe

how to winterize your retro wardrobe


The nights are getting longer, the days are getting colder, and one question is on every fashionable vintage gal’s mind: how am I going to keep looking cute all winter long? I see a lot of women asking about how to wear pinup clothes when the weather gets colder or being sad to put their pretties for the season, but a lot of the time fashion advice comes from Californians  and other warm-weather folk who, bless their hearts, just don’t know (or have forgotten) what Serious Winter can entail. I am a bonafide, true blue, blizzard-battered, polar vortex-surviving Northerner, and I am here to tell you that you do not have to give up on vintage style when the weather takes a turn for the worse.

Here are my top tips for dressing pinup in winter.

1. Accept the cold

It’s winter. It’s going to be cold. There’s no stopping it, and anyone who’s hoping for a magic bullet that will keep them toasty warm through the darkest subzero night is kidding themselves. But once you accept that the cold will come, it’s totally possible to stay comfy and cozy and still look cute.

2. Fleece-lined leggings/tights

These were 100% a gamechanger for me, and I credit them entirely with my ability to take a stand against pants, even when temperatures turn for the worst. I actually have to not wear my fleece-lined tights more often than not because I get too warm wearing them all day, but if you don’t run as hot as I do or are planning to be outdoors for any extended period of time, these will save your life.

3. Layers, layers, layers

You can’t just throw on a cardigan and call it layering in the depths of winter. Cardigans are great, but don’t forget about layering blouses and sweaters over or under dresses. Not only does it keep you warm, but it’s a great way to give new life to a dress and extend a spring/summer dress into a fall/winter one. (The Jenny dress is a perfect candidate for this – see how I styled my Halloween harlequin dress with a blouse.) An extra tanktop or t-shirt worn under a blouse or sweater can also help keep your core insulated. Wear an extra pair of leggings (or straight up long underwear) under your pants. Adding a scarf to an outfit can also dramatically increase how warm it is…every time I wear a scarf with a look, I end up taking it off since I tend to run hot during the day.

4. Decide what compromises you’re willing to make

I would be significantly warmer in the winter if I was willing to buy a not-cute puffy coat and wear a hat. But I’m not interested in smushing my hair, and I love pretty swishy coats. That’s a level of avoidable coldness that I accept. On the other hand, there’s no way I’m tromping over the icy death traps that are Wisconsin sidewalks in winter wearing heels. If I want to wear cute shoes, I have to be prepared to bring them along and change whenever I get where I’m going. It’s all about balance.

5. Plan ahead

Something that I’ll wear to a dinner out where I just need to run from my apartment to the car and the car to the restaurant is very different from what I’ll wear if I’m planning to walk to the theater after work (and then be walking back to my car when it’s even colder). Make sure you’re keeping the day’s plans in mind when you’re getting ready.

Follow these easy tips to keep looking cute all winter long! If you have specific questions, I’d be happy to put my Wisconsinite fashion sense to work on some cold weather clothing advice.



2 thoughts on “how to winterize your retro wardrobe

  1. I have a question! What about being prepared for rain/snow without giving up your vintage style? I’m going to New York in December & the cold I think I’ll be fine coping with it’s the wet weather I’m less prepared for. My big lovely vintage style winter coats are a long way off being water proof. I do have a fab plastic vintage style rain coat but that may keep me dry but it’s not going to keep me as warm. Help me!


    1. Ahh, the wet is always the worst! Personally, I do wear my wool winter coats even in wet weather…I figure if it’s good enough for the Navy, it’s good enough for me! If the fabric is thick enough, you shouldn’t feel the wet coming through while you’re wearing it, though it will need time to dry off after you come in from the rain/snow.


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