The holiday season has always been one that’s marked by reflection and nostalgia. This year, more than ever, looking to the past for fond memories and toward the future for optimism sounds like the right idea, which is why a roundup of retro holiday style photos to inspire your style right now feels oh-so-right. Of course, the holidays represent different sentiments for different individuals; Christmas, Hanukkah, Kwanzaa, New Year’s Eve — whatever you have in store this month, it’s probably safe to say you could use a pinch of inspo for the (socially-distanced) occasion.
Ahead, take a walk down memory lane and visit some of the most iconic women from the twentieth century. For a dose of high-octane glamour, be sure to bookmark photographs below of Lauren Bacall and Elizabeth Taylor. For a bit of ’70s disco flair, don’t miss Donna Summer or Bianca Jagger. Or, if European fashion tickles your fancy, there are a few snaps of icons like Jane Birkin, Sophia Loren, and Catherine Deneuve. In other words, if you live for a fashion flashback, by all means, enjoy the ride. Also, ‘tis the season for treating yourself to something nice so don’t miss the shopping picks to accompany each festive ensemble.
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Nostalgic Holiday Photo: Lauren Bacall in Pearls
Actor Lauren Bacall accessorized a strapless black dress with a corsage, a string of pearls around the neck, and a three-row pearl bracelet on the wrist. Simple, yet enduringly elegant.
Nostalgic Holiday Photo: Swimmin’ Around the Christmas Tree
Rita Aarons posed alongside her warm-weather Christmas tree for husband and photographer Slim Aarons. If you’re somewhere warm this year, celebrate in a different kind of suit.
Nostalgic Holiday Photo: ’70s Shine
A ’70s model swathed in a bell-sleeved metallic dress posed beside a tinsel tree. or a comfy alternative to a tight, spangled number try a floaty option.
Nostalgic Holiday Photo: Donna Summer Fireside Feels
The «Queen of Disco» posed for an at-home Christmas photoshoot beside the fire in a cozy cream turtleneck, slacks, and leather boots. The only thing to add is a festive tune and cup of cocoa.
Nostalgic Holiday Photo: Elizabeth Taylor Does Classic Feminine
In a sea of half-opened Christmas presents and in front of a silvery tree, actor Elizabeth Taylor epitomized 1950s femininity with an A-line dress and heels. Translate the moment to now with a pair of pretty mules.
Nostalgic Holiday Photo: Bianca Jagger at Studio 54
It doesn’t get much more festive than Bianca Jagger’s red gown and gold mask as seen above at a New Year’s Eve party thrown at the iconic Studio 54.
Nostalgic Holiday Photo: Festive Italian Flair
Italian actor Marina Berti trimmed her tree the ’70s way — with plenty of style and shine. Try a decorated knit for your own end of year celebrations.
Nostalgic Holiday Photo: Birkin and Gainsbourg à la NYE
Whatever your New Year’s Eve looks like this year, a subtle nod to Jane Birkin and Serge Gainsbourg is sure to make the evening feel a bit more memorable. Try a velvet top and full skirt for a quirky combination.
Nostalgic Holiday Photo: Charlotte Rampling in Snow Fringe
Though usually reserved for western-inspired dessert moments, actor Charlotte Rampling took her fringe for a spin in the snow during the holidays and the result was thoroughly inspired.
Nostalgic Holiday Photo: Catherine Deneuve On the Slopes
Après ski has never looked so chic as it did on Catherine Deneuve in this retro snap of the actor on holiday with her family during the Christmas season.
Nostalgic Holiday Photo: Love, The Fitzgeralds
If you’re not doing the can-can in front of your tree like Scott and Zelda Fitzgerald, you’re not doing it right. Try a drop-waist dress for a silhouette that’s true to their era.
Nostalgic Holiday Photo: Ginger Rogers Wearing A Silky Silhouette
Ginger Rogers proves voluminous shoulders aren’t a new concept. This wintry silk silhouette is ideal for any festive scenario.
Nostalgic Holiday Photo: Anna May Wong Beneath the Branches
Actor Anna May Wong brought a stylish new meaning to curling up beneath the Christmas tree in a long robe and silky slippers. Swap your cotton pajamas for this sleek combination this year.
Nostalgic Holiday Photo: Hillary in a Power Christmas Blazer
Leave it to Hillary Clinton to bring power dressing to the holidays with this stylish retro snap in front of a larger-than-life Christmas tree. An oversized blazer silhouette is easy to toss on over sweats.
Nostalgic Holiday Photo: 1930s New Year’s Sparkle
A glimpse at what New Year’s Eve looked like in 1939. Turns out, they had just as much fun as anyone else does now. Look for a festive ruffle sleeve to bring back the look.
Nostalgic Holiday Photo: 1960s New Year’s Eve
If all else fails, a puffed-up white frock should do the trick this New Year’s Eve.
Nostalgic Holiday Photo: Audrey Hepburn’s Festive Texture
Style icon Audrey Hepburn wore white gloves and sleek gold earrings with a gorgeous textured coat for the holidays. Santa Claus approved.
Nostalgic Holiday Photo: Josephine Baker Trims the Tree
Dancer and style icon Josephine Baker lent elegant ease to the holidays in this sleek hair wrap and simple dress.
Nostalgic Holiday Photo: Sophia Loren Dons Plaid
Not so into tinsel or sparkle? Try a pair of plaid pants like actor Sophia Loren’s, instead.
Nostalgic Holiday Photo: Diana Ross in Velvet
Music and style icon Diana Ross made velvet a must-wear fabric for the holiday season at this New Year’s Eve party shown above.
Nostalgic Holiday Photo: Rita Hayworth Goes Skiing
‘Tis the season for a stylish ride down the slopes, no? Follow Rita Hayworth’s lead and opt for solid colors in timeless silhouettes.
Nostalgic Holiday Photo: Jackie Kennedy Pairs Reds
A matching set cut in a saturated shade of red is perfect for the holidays, as illustrated by Jackie Kennedy Onassis.
Nostalgic Holiday Photo: Princess Diana (Plus Santas and Deer)
Keep in line with the winter aesthetic and go for an all-white ensemble with black tights for a Diana-inspired take on the holiday season.