Seven stunning vintage holiday season outfits

With December now underway, it’s time to take to think about the bevy of holiday get-togethers, both large and small, that may be looming on the horizon for you. From office shindigs to Sunday afternoon cookie baking parties, Christmas lunch at Grandma’s to a swish cocktail gathering, there is something ingrained in the festive spirit of the season that makes you want to dress up and really sparkle!

Whether you prefer to go all out (think head-to-toe sequins or yards of taffeta), shine on a small scale (a beaded cardigan, say, or a gorgeous pair of satin high heels), or meet somewhere in the middle (a shimmery brocade sheath dress, for example), few amongst us are sour on spicing up our wardrobe for the winter holiday season. Some may find that they already have a trove of fantastic pieces to pull from their own closets and drawers, others might be in need of some immediate shopping to supplement their winter garb, and others still may have a full closet, but feel the pieces there are getting a bit ho-hum and in need of some snazzy new companions to keep them company.

Whatever the case may be, I’ve compiled seven outfits, inspired by different types of vintage styles, to help inspire those days and nights in the coming weeks when dressing up is on the bill. (I myself tend to veer into the small to moderate amount of flash category, but when it comes to beautiful dresses with feminine touches, there’s no limit to how fancy I’ll go!)

Because the holiday season is already enough of a drain on our poor wallets as is, I’ve tried to keep the bulk of the items in these lovely looks on the more budget-friendly side (please note that the prices for all items in this post, unless otherwise specified, are in US dollars). It makes a lot of sense to approach your party wear with your pocketbook is mind, as the fancy pieces you purchase now may not get a great deal of use throughout the rest year, thus making their cost per wear higher than those of your more “everyday” type of garments.

If you feel like splurging on yourself however, now is the time! Treat yourself to a brand new (and by “brand new”, I mean “new to you”, the item itself may very well be vintage – and all the better if it is!) dress, string of beads, glistening brooch, elegant hat, or killer shoes. You’ve been good all year, so why not give yourself a little present this holiday season, too?


{Chronically Vintage's 2009 Holiday Fashion Guide}


~ The Sophisticate ~

Always impeccably dressed and on time to any event, the sophisticate favours elegant pieces in timeless shades that will see her through many Christmases to come. Strong lines and crisp tailoring are favourites, too, but she isn’t a minimalist by any means and enjoys the ingrained beauty of a regally inspired frock as much as that of a simple LBD.


{Long sky blue vintage evening coat with oriental inspired “frog closure” at neck , listed as fitting a “medium or large”, currently on sale for $30.00 from etsy seller Undone Eclectic.}



{Vintage faux pearl and gold toned metal clip-on earrings, $5.00/pair, from etsy seller Boxer Loving Lady.}



{Blue velvet, short sleeve 1940s dress with beautiful rhinestone detailing, fits up to a 35 inch bust/28.5 inch waist, $115.00 from etsy seller Planet Claire Vintage.}



{A forever classic, Chanel No. 5 in a 3.4 ounce bottle of Eau De Parfum, $115.00 from Essence of Perfume.com.}



{Navy blue and gold toned 1950s Margolin box purse measuring 8 inches long by 6 inches wide, $26.00 from etsy seller Bajue Boutique.}



{Stripped black and dark blue peep toe 1950s Herbert Levine heels, fits a size six, from GlamourSavvy.}



~ The Jitterbug ~

It’s as if you were born with the swing era in your blood. You love 1940s dresses and shoes, you own more bobby pins than you can count, and you’re always ready to cut a rug. Your style merges war era practicality with Hollywood glamour, part Rosie and part Rita, your holiday look could easily be home sewn or from Macy’s, but no matter what, it has a truly timeless feel to it.


{1940s golden wheat hued straw hat with red grosgrain ribbon, measures 20 inches at the interior point of the ribbon, $70.00 from Damn Good Vintage.}



{Dior lipstick in shade #622 “Graffiti Red”, 3.5 gram (0.12 ounce) tube, $23.50 from StrawberryNET.com.}



{Gold toned (vermeil over base metal) floral leaf brooch with red and clear rhinestone accents (swivel pin back), measurements not specified, $16.00 from etsy seller Carmen and Ginger.}



{1940s two piece red and gold crepe dress with matching belt, blouse fits up to a 38 inch bust/29 inch waist (skirt fits up to a 28 inch waist), $55.00 (for all three pieces) from etsy seller Little Things Vintage.}



{1950s “Kelly style” red, gold and black beaded handbag with black Bakelite handle, 11.75 inches long by 8 inches high, $169.00 from etsy seller Archivia.}



{Red 1940s velvet peep toe shoes with ankle straps (deadstock), size 8.5, $125.00 from etsy seller Planet Claire Vintage.}



~ The Gamine ~

Whether young on paper or at heart, the gamine falls head-over-heels for pieces that are sweet and airy, ethereal and delicate. She may sport a shoe with a stacked wooden heel, but the body of that shoes is bound to be made of silk, satin or another gentle material. She loves chiffon, bows, jewels in her hair, and styling her outfits like those looks one finds in the outdoors-in-a-meadow fashion shoots of couture fashion magazines.


{Handmade peach and peacock feather headband style fascinator with gold toned metal and rhinestone detail, $15.00 from etsy seller Plumes et Fleurs.}



{Hand woven, pastel faux pearl flapper era necklace, 36 inches long, $12.50 from etsy seller True Colours For You.}



{Gold toned fan shaped vintage compact made by (and signed) Henriette, $95.00 from Michelle’s Vintage Jewelry.}



{Beguiling 1940s peach hued tulle and lace formal, full length dress, fits up to 42 inch bust/31 inch waist, $84.00 from etsy seller Fab Gabs.}



{Pale dusty pink and silver beaded 1920s purse (that was made in Germany), 8.5 inches long by 4.5 high, $24.00 from etsy seller Vintagous.}



{Peach (pale pink) t-strap peep toe, AK Anne Klein shoes with a 3.5 inch tall heel, available in modern foot sizes, $49.99 from Shoefest.com.}



~ The Bombshell ~

Alluring, playful and perpetually channeling her inner pin-up girl, the bombshell adores pieces that showcase her sensuous curves. She veers towards either skin-tight skirts and dresses or those with copious amounts of volume – perhaps requiring a crinoline to hold up their abundance of fabric. Her favourite accessories are the lingering scent of her signature perfume and a mega-watt smile which is always dressed in red lipstick.


{Mauve and taupe hued rose and raspberry red jasmine blossom floral hair clip, measures 6 inches long, $32.00 from Retro Glamour Girl.}



{“Leopard Love” velboa faux fur vintage inspired capelet (stole) with black tie bow, one size fits all, $38.00 from etsy seller Talulah Blue.}



{Wiggle style burgundy velvet dress with a portrait neckline, available in stock in size “small”, $115.00 from Babygirl Boutique (on a personal note, I’ve been lusting after this particular dress for months!).}



{Shiny black vintage patent leather quilted handbag on a delicate silver chain, 9 inches long by 6.5 inches high, $22.00 from etsy seller ebielli.}



{Seemed, 15 denier fully fashioned stockings (thigh highs) with a classic point (French) heel available in black (as shown) or nude, £17.75 (UK pounds) from What Katie Did.}



{Black satin 4 inch high wedge heel shoe with rosette detail, available in sizes 6 to 12, $48.99 from Retro Cuties.}



~ The Sexy Secretary ~

Long before the office pool gals from Mad Men burst on the scene you were rocking the sultry secretary look to the max. With a penchant for pencil skirts, upswept hairdos, and prettily manicured nails, you love to extend these same style ideas to your holiday finery, adding in a touch more eye make-up and perhaps one of those swanky suit clad Sterling Cooper style gents on your arm.


{Bright blue velvet vintage pill box hat with bow, measuring 21 inches at the brim, $35.00 from etsy seller Becky Drolen Vintage.}



{Shiny blue and soft cream floral clip-on earrings with rhinestone and faux pearl details, $9.00/pair from etsy seller Mean Old Bags.}



{Silver toned, stretch band ladies vintage Bulova watch (note this timepiece needs a new battery and possibly some other remains to set it working again), length measures 5.5 inches before being stretched, $44.00 from etsy seller Bajue Boutique.}



{Light aqua blue 1950s satin wiggle dress with matching bolero jacket, fits up to a 34 inch bust/25 inch waist, $105.00 from etsy seller Sara’s Attic.}



{Vintage silver hued, top clasp purse on a chain strap, 9 inches long by 5 inches high, $8.69 from etsy seller An Eclectic Collection.}



{Gorgeous 1960s multi-coloured silk (I’m guessing) brocade flats (with a half inch heel), fits a size 7, $20.00 from etsy seller Funky Fugal Fashions.}



~ The Girly-Girl ~


The antithesis of a tomboy, you embrace your feminine side with a force to be reckoned with. From scads of lace to piles of jewelry, floral prints to soft, luxurious fabrics, you seek out and gleefully sport pieces that personify the elegance of ladies wear to an absolute tee.


{Long, soft white/ivory faux mink fur wrap (stole), measures 65 inches long by 14 inches wide, $55.00 from etsy seller Romancing Juliet.}



{1950s coral pink lace, short sleeve party dress with cap sleeves and a velvet bow accent at the waist, fits up to a 32 inch bust/25 inch waist, $68.00 from etsy seller Cheap Vintage.}



{Ivory white hued vintage wrist length gloves with pretty floral embroidery detailing, measurements not specified, $28.00 from etsy seller Blueberry Deluxe.}



{1950s vintage clutch purse with a silk flower vignette behind a layer of plastic overlay surrounded by a gold hued metal frame. Purse measures 11.5 inches long by 5.5 inches tall, and is $45.00 from etsy seller The Greedy Seagull.}



{“All My Love” 1950s style golden brass hued metal charm bracelet, measures 8 inches long, $89.00 from Babygirl Boutique.}



{1950s pink and green rose print heels with rhinestone detailing on the front, size 7.5, $32.00 from etsy seller Planet Claire Vintage.}



~ The Christmas Queen ~

While you’d never in a million years risk being caught dead in a tacky Christmas sweater, you utterly adore embracing the colours of the season and weaving them not only into the holiday decor of every room in your home, but also into the pieces you wear when gathering to celebrate. From the red of Santa’s suit to pine needle green, you’re as decked out and ready to shine this season as a string of vintage Christmas lights!


{Early 1950s green velvet hat with rhinestone trim (labeled made in France), 11 inch diameter, $36.00 from etsy seller Babylon Sisters.}



{1950s festively wrapped Christmas gift set of clip-on earrings and a (swivel clasp) brooch in gold toned metal and plastic, $24.00 (for the set) from etsy seller Carmen and Ginger.}



{Three piece set of vintage (1930s, 40s and 60s) red and green Bakelite bangle bracelets, $44.00 (for all three) from etsy seller Bakelite Bakery.}



{1950s emerald green velvet and satin dress with tulip (bubble) style skirt, fits up to a 35 inch bust/25 inch waist, $135.00 from etsy seller My Favourite Vintage.}



{1950s golden lucite and woven reed handbag with lucite handle and clasp (and a white “spill proof” vinyl lining) in excellent condition. Measures 10.75 inches long by 8.75 inches high; $65.00 from etsy seller BBBDesigns.}



{1940s Daniel Green peep toe slip on heels (mules) in a sparkling golden fabric with rosette details, fits size 6, $110.00 from etsy seller Peaceforevermore.}


After putting together this delightful selection of looks, I suddenly have the intense urge to send out party invitations and don an evening dress! While I wait for my RSVPs to come back (naturally you’re all invited), I’d love to hear your thoughts on these styles.

Do you identify with some of the fashionista profiles above or does your winter holiday wear veer in an entirely different direction? Whatever your taste in festive garb, I hope that you all get a chance to dress up this season and celebrate to your heart’s content!