The 17 looks here run from a black turtleneck and a pair of gingham capris you could buy this week to a strapless embroidered ball gown and a tiara-topped pink cocktail dress that only make sense at a gala or a themed party.
Occasion decides the outfit: for daily wear, the Classic Black Turtleneck, the Belted Trench Coat or the Polka-Dot Fit-and-Flare Dress hold up best, while a wedding calls for the Tea-Length Wedding Dress and Veil or the Balmain dress with its rose crown.
1. Black Satin Boatneck Dress
Satin catches light in a way matte crepe never will, which is why a black boatneck in this fabric needs almost nothing else. Long gloves and a strand of pearls finish it, and I would stop there.
The neckline runs wide and straight across the collarbones, so it flatters narrow and broad shoulders alike. Skip a necklace that sits high; pearls at collarbone length or longer keep the line clean.
Pressing matters more than usual, since satin shows every crease.
2. Gingham Capri Pants
Red gingham capris are the easiest way I know to make a plain black top look planned. Keep the top fitted and simple, a tee or a fine knit, and let the check do the talking.
Capris hit at the calf, so flat shoes suit them best. Ballet flats or low sandals show off the ankle and keep the proportions tidy.
Choose a small, even check over a large one if you want the pants to read as classic rather than picnic-ready. They work best in warm weather, with little else needed.
3. Sleeveless Black Givenchy Sheath
Nothing in a closet does more work than a sleeveless black sheath, and this version proves it with just white gloves added.
The column shape skims the body instead of clinging, so it suits most figures when the hem lands near the knee.
Buy it in a fabric with some weight, so it hangs smoothly. Then decide the styling once: gloves for a formal evening, bare arms for everything else.
I would pick a plain neckline, since the dress should be the quiet part of the outfit.
4. Belted Trench Coat
A tan, double-breasted trench with a cinched belt gives you a waist on days when nothing underneath does. Tie the belt rather than buckling it, and the knot sits flatter and looks easier.
Sunglasses are the simplest finish for a city street. Boots work too, and I like them when the weather turns, since a trench is a light layer rather than a warm one.
If you are petite, check that the hem stops near the knee; a coat that runs too long swallows your height.
5. Classic Black Turtleneck
A dark turtleneck is the least fussy piece in the whole Audrey Hepburn wardrobe, and probably the one you can recreate today. Look for a fine-gauge knit in black or deep navy that sits close to the neck without bunching.
Fitted works better than slouchy for this look; a snug knit keeps the outline sharp. Wear it with slim trousers or a pencil skirt, and leave jewelry off, since the neckline does the framing.
Cashmere costs more, but a good cotton blend gets you close.
6. Sabrina Embroidered Ball Gown
A strapless white gown with floral embroidery is a showpiece, so I would save it for a formal event like a gala or a black-tie wedding. The embroidery adds texture, which means the silhouette can stay simple.
Fit at the bodice decides everything with a strapless neckline. Have it tailored so it stays up without tugging.
Hold the accessories to a minimum: small earrings, maybe a clutch. Anything more competes with the stitching.
7. Tea-Length Wedding Dress and Veil
A tea-length wedding dress with a full skirt and a short veil suits a small ceremony better than a cathedral one. The hem lands between knee and ankle, so you can walk, dance and climb stairs without holding fabric.
Keep the veil short, as the dress shows, and skip a train. A ballet flat or a low sandal leaves the hem in plain view, and the dress stays light instead of heavy at the bottom.
Choose a fitted bodice so the full skirt has something to balance against.
8. Silk Headscarf with Sunglasses
A patterned silk scarf tied over the hair, with dark sunglasses, is the quickest way I know to look finished on a bad hair day. The yellow print here gives the outfit its color, so the rest can stay plain.
Pick a scarf with a pattern you love, since it frames the face. Fold it into a triangle and tie it under the chin or at the nape.
Sunglasses should be dark and fairly large. Open-top cars are ideal, but a windy sidewalk works too.
9. Black Capri Pants and Blouse
Cream button-down, cropped black trousers, strappy heels: the contrast does all the work, and the ankle gets to show.
The maker of this look gives 2 rules I agree with. Stick to black, with no prints, and if you add a jacket, go very short or maxi, never half way, because a middle length throws off the balance.
Tuck the shirt in so the waist stays visible. A capri hem works best when it stops a couple of inches above the ankle bone, so the ankle shows and the leg doesn’t get chopped.
Flats work too, though heels lengthen the leg most.
10. Polka-Dot Fit-and-Flare Dress
Navy with white polka dots is a safer choice than black for daytime, and a cinched waist with a full skirt does the flattering.
This is the shape I reach for when I want a dress to work on most figures.
Look for a small, evenly spaced dot; large ones can feel costume-like. The waist seam should sit at your natural waist, not below it.
Wear it with flat shoes and little jewelry. The print already has plenty to say.
11. Wide-Brim Hat and Midi Dress
A wide-brimmed hat changes how a plain dress reads, so I would keep the dress simple: sleeveless, midi length, a thin belt at the waist. A light color keeps the hat from feeling heavy.
White gloves and heels complete the look, though gloves are optional if the day feels too dressed up. The brim shades your face, but it can hide it in photos, so tilt it slightly back.
Choose a hat that fits snugly so it stays on in wind.
12. White Shirt and Belted Midi Skirt
Short sleeves, a wide-belted midi skirt and flat sandals make the easiest outfit to walk in all day, with nothing to tug or adjust.
Tuck the shirt in and cinch the belt at the natural waist, so the skirt has shape.
Wide belts suit shorter torsos best; on a long torso they can look busy, so try one and check the mirror.
On a midi skirt, I look for a hem that lands just below the knee and well above mid-calf; that range keeps the legs from looking cut off.
Flat sandals keep it easy for travel and hot days.
13. Pink Cocktail Dress with Cape
A pink sequined cocktail dress with a bow at the waist, a matching cape and a tiara is party dressdressing at its most complete. The cape covers the shoulders, so the dress itself can stay sleeveless and simple.
Keep the pink to one shade across the dress and cape. Sequins already catch plenty of light, so I would skip other sparkle except the tiara, and leave off a necklace.
For a holiday party or a themed night, this is a fun one to try. It is not an everyday outfit.
14. Sheer Wrap and White Pillbox Hat
Sheer white over black is a quiet contrast, and a tall white pillbox hat repeats it near the face. The black sheath stays sleek, and the shawl softens it without adding bulk.
Pick a shawl light enough to drape rather than bunch at the elbows. A pillbox sits level on top of the head, so check the angle in a mirror; tilted too far, it slides.
I like this for a formal daytime event, where a black dress needs a touch of white to feel dressed.
15. Blue Lace Short-Sleeve Gown
Soft blue lace in a floor-length cut, with short sleeves and a ribbon bow at the waist, reads gentle rather than grand. The bow marks the waist, so the long skirt doesn’t swallow your shape.
Lace works best when it is lined, so nothing shows through that you did not plan. Short sleeves also make the gown easier to wear for a spring wedding or a dinner than a strapless one.
Keep the shoes and jewelry plain. The lace already carries the detail, and a pale blue like this looks best with little added.
16. White Skirt Suit and Black Hat
Head-to-toe white looks sharp when every piece is tailored: a fitted blazer, a midi skirt, pointed pumps. The black hat and a small clutch break up the white, so it doesn’t turn flat.
Choose white in a thick, opaque fabric, since thin white shows everything. A hem just below the knee keeps the skirt in proportion with pumps, and the pointed toe lengthens the leg.
Black works best in just 2 places, the hat and the bag, and everything else stays white. It suits spring and summer best, and it needs careful handling, as white marks easily.
17. Balmain Wedding Dress with Rose Crown
A white wedding dress paired with a crown of roses suits an outdoor ceremony, where fresh flowers belong. The crown stands in for a veil, so the dress can stay simple.
Order the crown close to the day, since fresh roses wilt, and have it sized to your head so it sits level. If you want it to last, ask a florist about a version with silk flowers.
Keep your hair down or loosely pinned. A heavy updo would crowd the roses.
