Jacqueline Kennedy Onassis dressed in two distinct eras. In the White House years it was structured skirt suits, shift dresses and pillbox hats; later, in New York and on the Cape, it was headscarves, big sunglasses, trousers and jeans. Both phases rest on the same habits: clean tailoring, a narrow palette and almost no visible branding. When clients bring me a photo of her, my job is to keep those habits and lose the period costume. Below are 20 outfits drawn from her best-known looks, each built head to toe with pieces you can buy or already own. They also make a sound starting point for an old money capsule wardrobe.
Wearing Jackie Without Looking Like a Costume Party
The fastest way to ruin a Jackie-inspired outfit is to copy all of it at once. A pillbox hat, a matching tweed suit, white gloves and a bouffant together read as dress-up. I take one signature element per outfit and keep everything around it modern: today's denim cuts, current shoe shapes and simpler hair.
Proportion matters too. Her boxy jackets were cut short with a high armhole, which suits a slim, straight frame. If you're curvy or have a full bust, a boxy jacket can fall from the widest point and hide the waist, so I'd look for one with darts or princess seams that shape it slightly. Petite frames do well with the cropped length; taller women can go a little longer and still keep the look.
- Pick one hero piece: the scarf, the sunglasses, the tweed or the pearls.
- Keep shoes current. A low block heel or a modern loafer reads today; a very pointy period pump can tip it into fancy dress.
- Use her palette rather than her exact outfits: navy, cream, camel, black, white and soft pastels.
1. Pink Tweed Skirt Suit And Pillbox Hat
The raspberry pink suit is the one everyone pictures: a double-breasted bouclé jacket with a navy collar and gold buttons, a slim matching skirt and a pillbox hat. Copied exactly, it looks like a costume. I'd take a soft pastel tweed jacket and knee-length skirt in a textured wool blend, then add a navy top-handle bag, low block-heel pumps and a single strand of pearls. A slim headband does the hat's job without the theatre. Bouclé loops snag on rings and bag hardware, so carry the bag by the handle rather than over the arm.
2. Trench Coat With Turtleneck And Knee-High Boots
Her off-duty formula was a double-breasted trench over a fitted turtleneck with knee-high boots, sometimes livened up by a red striped knit under navy. Today I'd use a beige or camel trench in a straight, slightly roomy cut, a black or navy fine-knit turtleneck, and dark slim or straight trousers tucked into leather boots with a low stacked heel. Tucking only works if the trouser leg is narrow enough to sit flat inside the boot shaft; bunching at the knee ruins the line. Small gold hoops and a structured leather crossbody keep it tidy for fall days or early spring errands.
3. Navy Blazer With Cream Trousers And Two-Tone Accessories
Navy over cream was one of her favorite early-1960s contrasts, and it still looks sharp in any season. Start with a tailored navy wool blazer with gold crest buttons and a light cream crew-neck knit or cotton blouse under it. High-waisted cream trousers with a straight or slightly tapered leg keep the body long. Navy and cream spectator slingbacks or plain navy flats, a two-tone structured bag, pearl clip earrings and a slim silk scarf knotted at the neck or on the bag handle complete it. Cream trousers show every mark, so I always suggest a pair with some weight; thin cream fabric shows pocket outlines and underwear.
4. Oversized Sunglasses And Silk Headscarf
The image of her walking through Manhattan with a silk scarf tied under the chin and dark oversized sunglasses defined her post-White House years, and designers keep returning to it. Choose a square silk scarf in a quiet print or solid neutral, fold it into a triangle and knot it under the chin or at the nape. Put a light trench or swing coat over a simple black or ivory knit dress. Big tortoiseshell or black frames with a soft cat-eye or round shape get the face right. Leather driving gloves and a compact shoulder bag finish it. Silk slides on smooth hair, so a few bobby pins under the scarf keep it in place on a windy street.
5. White Jeans With Navy Button-Down Shirt
Her casual summer uniform showed that jeans could look as composed as a suit: white straight-leg jeans with a navy button-down, sleeves rolled to just below the elbow and the top button open. I'd choose high-rise white denim heavy enough to be opaque, a light navy cotton or silk-blend shirt, and brown riding boots in cool weather or flat leather sandals in summer. A thin brown belt with a gold buckle connects the browns, and big sunglasses with a plain gold watch keep it relaxed. Roll the sleeves in neat, wide turns rather than bunching them; that small detail carries the whole look.
6. Pastel Shift Dress With Pearl Jewelry
Her White House closet was full of sleeveless shifts in powder pink, pale yellow, mint and ice blue, often in silk shantung or light wool crepe. A shift hangs from the shoulders with a modest neckline and lands at or just above the knee. Fit at the shoulder and bust is everything, because the dress has no waist seam to hide a poor fit; take it in at the sides if it tents. Add layered pearls, pearl studs and a white or metallic clutch, with kitten heels or ballet flats in a matching neutral. A cropped cardigan or a light wool coat over the shoulders handles cooler rooms without breaking the line.
7. Cropped Trousers With Ballet Flats And Cardigan
Slim trousers cut just above the ankle were her travel and daytime choice through the 1970s. That cropped length puts the shoe on show, which is why ballet flats with a round toe and tiny bow suited them so well. Build it from tailored black or charcoal cropped trousers, a fine cream or heather gray cardigan worn buttoned, and a cotton shell or short-sleeve knit underneath. The crop should end at the narrowest part of the ankle; an inch higher and it looks like the trousers shrank. Black leather flats, a neutral top-handle bag and a slim leather-strap watch make it right for museums, lunches or a long city walk.
8. A-Line Skirt With Fitted Crop Jacket
A boxy cropped jacket over an A-line skirt was one of her most recognizable First Lady silhouettes. The short jacket with a firm shoulder contrasts neatly with the fuller knee-length skirt. Look for a collarless tweed or wool-blend jacket that ends at the high hip, with a matching A-line skirt. A silk shell or crew-neck top in ivory or a pastel goes underneath. I check where the jacket hem falls against the skirt's waistband: it should overlap by a little, or a strip of shell shows and the set looks disjointed. Low block heels, a small structured bag and a subtle brooch at the lapel finish it.
9. Tailored Trousers With Silk Blouse And Gold Jewelry
Later on she simplified into a quieter uniform: high-waisted trousers in black, navy or camel, straight or slightly wide, with soft silk blouses and very little gold jewelry. For this version, pick wide-leg trousers in a neutral wool blend, a champagne or ivory silk blouse with a soft tie or bow at the neck, and leather slingbacks. A gold chain, small gold hoops and a structured leather tote are all you add. Have the trousers hemmed with the slingbacks on so they almost cover the heel. A bow blouse can look fussy on a short neck, and an open collar with the tie left loose solves that.
10. Black Turtleneck With White Trousers
Black turtleneck with white trousers became one of her later signatures, and it's as graphic as an outfit can be. Choose a fine-gauge black merino or cashmere turtleneck tucked into high-rise white trousers with a fluid wide leg. Black suede pointed flats or low mules, a heavy gold chain bracelet, dark oversized sunglasses and a black leather shoulder bag with gold hardware give the dark top half enough weight to balance the pale legs. Lint is the enemy of this one: black knit picks up fluff and white trousers pick up dye transfer from dark bags, so carry the bag on the opposite side. For evening, add a bolder lip and a silk scarf.
11. Cable Knit Sweater With Riding Boots And Straight-Leg Jeans
Country and Cape Cod weekends meant sturdier clothes, and a chunky cable knit sweater with tailored jeans and tall riding boots was her formula for coastal New England. I'd use an ivory cable crew-neck, dark straight-leg jeans with very little stretch and brown leather knee-high boots with a low heel and an ankle strap. A wide brown belt, tortoiseshell sunglasses and a quilted or suede crossbody finish it. Real riding boots are stiff for the first few wears and need breaking in around the ankle, so wear them around the house before a long day out. You don't need a stable nearby to enjoy this one.
12. Tweed Dress With Gold Button Detail
Her one-piece answer was often a tailored tweed shift with gold buttons running down the front or set on the cuffs and pockets. Nubby bouclé or herringbone in ivory, pale blue or soft pink looked expensive without any logo. Today, choose a knee-length tweed dress with bracelet sleeves, a clean round or jewel neck and gold crest or coin buttons. Low block heels in nude or metallic leather, a structured ivory or black bag and a slim pearl bracelet suit it. Make sure the dress is lined, since loose-woven tweed can scratch and also stretches at the seat. A fine merino cardigan or cropped jacket over the shoulders covers colder days.
13. Denim On Denim With Oversized Tote And Sunglasses
Her 1970s off-duty denim showed that head-to-toe jeans can look polished when the fit is precise. She often wore a denim button-down tucked into high-waisted flared or straight jeans, with large sunglasses and a soft slouchy shoulder bag. For a modern version, take a medium-wash denim shirt with a point collar, high-rise jeans in a slightly lighter or matching wash, and brown heeled sandals or clogs. I'd keep the two washes clearly different or almost identical; washes that are nearly but not quite the same look like a mistake. A large tan or dark brown hobo bag, oversized square sunglasses and thin gold hoops finish it.
14. Gingham Sundress With Wide-Brim Straw Hat
At the family compound in Hyannis Port she wore plain sundresses suited to beach walks, and a yellow-and-white gingham dress with a wide straw hat and big gold earrings is among her happiest summer looks. Recreate it with a midi gingham sundress in a sunny hue, a structured wide-brim straw hat with a black or tan ribbon, and flat leather sandals. Add a woven tote and chunky gold earrings. A hat brim needs to clear the shoulders; if it's wider than your shoulder line it can overwhelm a petite frame. Wear it to a farmers' market, a garden party or a seaside trip.
15. Skirt Suit With White Gloves And Structured Handbag
Opera-length white gloves won't fit most modern days, but the shape around them still works: a trim collarless jacket, a slim knee-length skirt and immaculate accessories. Pick an ivory or pale blush skirt suit with a cropped, boxy jacket and a straight skirt. Put a fine white or cream shell underneath and carry a structured beige or taupe top-handle bag. Low nude pumps and pearl drops finish it, and a neatly folded pocket square at the lapel adds a little texture. Pale suiting marks easily at the cuffs and seat, so I'd suggest a wool with some twist in the yarn; it sheds creases far better than a flat crepe.
16. Flared Jeans With Printed Blouse And Clogs
Into the 1970s her style relaxed a great deal. The prim suits gave way to dark indigo flares and soft printed blouses in small florals or paisleys, grounded with chunky leather clogs or platform sandals. A high rise on the jeans balances the volume of a tucked blouse. Today I'd pair high-waisted flares with a gentle kick at the hem, a silk or crepe de chine blouse in a muted botanical print, and dark brown clogs with a wooden heel and gold buckle. Flares should almost touch the floor in the shoes you'll wear, or the leg looks cut short. A thin belt, a gold pendant and a caramel shoulder bag finish it.
17. Midi Skirt With Slingback Heels And Twin-Set Cardigan
She often started from a twin set, a short-sleeve crew-neck knit with a matching cardigan, and added a soft midi skirt that moved as she walked. With low slingbacks it looks ladylike without being stiff. Choose a cashmere or fine wool twin set in pale pink, heather gray or powder blue and tuck the shell into a gently flared midi skirt in a neutral. Tuck the knit in fully and pull it up a touch at the sides, otherwise thin knit bunches at the hips under the skirt. Nude kitten-heel slingbacks, a pearl strand under the cardigan collar and a small structured bag finish it, with a light trench over the shoulders for a coffee date.
18. High-Waist Trousers With Cashmere Sweater And Loafers
This one looks the most current of all her outfits: high-waisted fluid trousers, a soft cashmere sweater and polished loafers, close to the quiet office dressing people wear now. The trousers sit at the natural waist and fall straight or slightly wide, while the sweater drapes loosely over the torso. Pick camel or dove gray lightweight wool trousers, a cream or charcoal cashmere crew neck and black or cognac loafers with gold hardware. A slim belt, a plain gold watch and a textured leather tote finish it. Tuck just the front of the sweater, because a full tuck of cashmere into wool trousers adds bulk right at the waistband.
19. Cape Coat With Dark Skinny Jeans And Leather Gloves
She understood what a cape coat does: it gives a clean, sculptural outline without the bulk of a regular coat. Chocolate brown wool or winter white over lean dark trousers and fine leather gloves was one of her memorable travel outfits. To build it, choose a knee-length cape or cape-sleeve coat in camel or black wool blend over a fine black turtleneck, with dark skinny jeans or tailored ponte leggings. Tall black boots with a modest heel and long black or brown leather gloves suit it. A cape has no real sleeves, so carrying a shoulder bag is awkward; I'd stick to a structured top-handle bag and gold drop earrings.
20. Sleeveless Column Dress With Kitten Heel Slingbacks
For evenings in the late 1960s and 1970s, she often chose sleek sleeveless column dresses over big gowns, ending just below the knee or at mid-calf. The shape is minimal, so the fabric carries it, usually silk crepe, heavy satin or fine wool. Today, start with a sleeveless column dress in a rich jewel tone like emerald, sapphire or deep wine, in a substantial matte fabric. A column shows what's underneath, so smooth, flat-edged underwear and a lining are not optional here. Metallic or tonal kitten-heel slingbacks, a fine gold cuff, a small velvet or satin clutch, diamond or pearl studs and swept-back hair finish it.
Three Ways to Tie a Silk Square
A silk square shows up in several of these looks, and it's the cheapest way to borrow her style. Larger squares are easiest for head ties, while smaller ones suit the neck and bag. Silk twill holds a knot better than slippery charmeuse.
- Under the chin: fold the square into a triangle, lay the long edge across the forehead or just behind the hairline, cross the ends under the chin and tie at the side of the neck.
- At the nape: same triangle, but bring the ends behind the head and knot them low under the hair.
- At the neck: fold into a narrow band, wrap it once and knot it a little off-center so it doesn't look like a uniform.
Tweed and Bouclé Need Different Care From Cotton
Loose weaves like bouclé catch on jewelry, zips and velcro, and a pulled loop is hard to fix neatly. Store these jackets on wide, shaped hangers so the shoulders keep their form, and give them room in the closet. Most need dry cleaning, so spot clean small marks and air them between wears rather than cleaning after every outing. If a loop does pull, ease it back to the inside with a crochet hook instead of cutting it.
Her Real Secret Was Tailoring
Her wardrobe lasts because she ignored most trends, bought pieces that fit and wore them often. The 20 outfits above adapt easily to a modern closet, for weekdays, travel or a dressier evening. What links them is restraint: clean lines, neutral or soft colors, good fabrics and accessories that support the outfit instead of competing with it. I'd start with the one or two looks closest to how you already dress, have the key pieces altered properly, and add from there.
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