There’s just something about leaves crunching underfoot and sparkly snowflakes falling that makes us feel a little nostalgic for times gone by, even times we never lived through. Admit it:  On that first perfect snowfall, you start hearing Frank Sinatra croon in your head as you imagine yourself as the romantic lead of some old, vintage movie.  Am I right?

It’s OK, you’re not alone.  For whatever reason, the colder temps and winter fashion bring out the movie star in us all. And because winter is a time when we naturally tend to wear more modest, classic styles, it’s easy to make your outer look reflect your inner retro fashionista or fashionisto.

Dressy Coats

Vintage winter fashion

I know all too well that sometimes Polar Vortex weather conditions demand serious outerwear whose main priority is utility, not style.  And on those days, you’ve got no choice but to wear the down parka that makes you look like the abominable snowman.  But, when temperatures are slightly more moderate, you need a super stylish coat that looks just as chic as the outfit underneath.

Ladies should look for coat styles that have the cut of an old swing dress – a fitted bodice and a somewhat voluminous, circular skirt.  Black is always a safe bet for outerwear, but your vintage style will shine ever more in colors like navy blue, kelly green, red, mustard, or a dusty pink.

For the gents, you can’t go wrong with a classic pea or duffel coat in black, navy or camel wool.  And the great thing about real wool is that it feels as warm as it looks – you can actually get an official navy pea coat from the Army Surplus store for just $150.  The key for men is making sure that it fits you like a glove.  Buy something that you like and then take it to a tailor to get a custom fit that will instantly elevate the piece.

Chic Hats

Vintage winter fashion

These days hats are usually more about function than form – we throw on some fuzzy crochet beanie when it’s cold out and that’s about it.  But in years past, hats were considered an integral part of an outfit and a stylish girl or guy wouldn’t consider leaving the house without one.  So, wearing a chic head topper with retro flair is the surest way to add vintage influence to your look…and don’t worry, you can pull it off.

For ladies who are used to wearing a simple hat just to keep warm, this will be a change.  And you may feel a little self-conscious at first, but rest assured that you look fabulous – the insane amount of compliments you receive from admirers will surely prove that.  Of course you have to choose something that compliments your face and hair style, but it’s hard to go wrong with classic designs like a beret, a fedora or a cloche.  A pretty beret worn jauntily to the side, with your elegant swing coat, will instantly lend a classic style to your look and may even result in adding a bit of Hepburn-eque swagger to your step.

The vintage hat game is one that guys can (and should) play too.  Men almost invariably look cool in a timeless flatcap or fedora…yes, I said fedora.  Though the design has been famously mocked in recent years, it is a killer look for a man with style, when it’s done right.  The first thing to understand is that what you probably think of as a silly-looking fedora is actually a trilby. A true fedora has a wider brim all around and when it’s worn with an elegant overcoat, makes you look Don Draper level handsome and cool.  That said, you do risk looking a bit ridiculous when you pair it with jeans and an Ed Hardy shirt.

Leather Gloves

Millennial Magazine presents vintage winter fashion

Yes, I know we all have about 10 pairs of those cheap knit gloves that are stuffed into the pockets of all of our winter jackets and coats. And then there’s the thermal pair we wear when scraping snow off the car in the morning.  But do you have a pair that looks stylish when you’re out on the town trying to look like you just stepped out of a ’63 Chevy?  If not, you’d better start looking for the perfect pair now.

For both men and women, the only real choice is leather (or faux leather).  It’s worth investing in a high-quality pair that you’ll have for years.  And you can have a bit of fun with styling – look for ones with interesting touches like visible stitching or decorative accents.  A pair that contrasts with the color of your coat is always a nice way to add some whimsy and interest to your look.  The right ones will keep you feeling warm and looking chic.

Saying goodbye to your easy, breezy summer wardrobe (and the summer weather) can be sad.  But you can offset some of those winter blues by infusing your outwear collection with vintage style.

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Nicole Betti


Chicago, IL

Nicole Betti is a vintage fashion fanatic, style writer and founder of Gold Coast Couture, a boutique dedicated to women’s hats, fascinators and accessories. She loves helping women discover the power of a fabulous hat.

All posts by Nicole Betti

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