Measuring the Right Midi Length for Your Height
Midi is a range, not a single length. It runs from just below the knee to just above the ankle, and the part of that range you choose changes how every outfit below looks.
I find the right length by having a client stand barefoot in front of a mirror and hold a skirt up against her legs. The narrowest part of the calf, usually a few inches below the fullest part, is the most flattering place for a hem. A skirt that ends right at the widest point of the calf makes the leg look heavier, whatever your size.
- Petite frames usually look best with a hem just below the knee, or with a mid-calf length worn with a slight heel or a shoe in a skin-toned color.
- Taller women can wear the long end of midi, just above the ankle, with flats.
- Measure from your natural waist to the hem point you like, then compare that number with the length listed online before ordering.
- If you love a skirt that's too long, a hem is one of the cheapest alterations. Just ask for the same depth of hem as the original, so it still hangs properly.
1. Start#
For many women in our 60s, the midi skirt ends up being the piece that solves the most problems. It covers the knee, moves when you walk and works with flats, which matters more every year. Wrap and paneled styles are the ones I reach for first with clients this age, because they give the waist some shape without squeezing it. Getting a midi to look current rather than dated comes down to three decisions: where the hem lands, what the fabric does when you move, and which shoe sits under it. The 20 outfits below cover lunches, office days and evenings out, with what I'd check before wearing each one.
1. Midi Skirt With Button-Down Shirt and Loafers
A crisp button-down tucked into a midi skirt is the outfit I'd build a whole wardrobe around. Use a white or pale blue cotton shirt with the sleeves rolled once, and tuck it fully into a navy or black crepe skirt. Crepe has enough weight to hang straight, so the shirt fabric doesn't bunch at the hip. A thin leather belt marks the waist, and cognac or black loafers keep it grounded. Add a structured leather tote and gold studs. The tailored top over a fluid skirt is what makes it look completely ageless, from coffee dates to board meetings.
2. Midi Skirt With Turtleneck and Ankle Boots
When the temperatures drop, a fine-gauge turtleneck tucked into a midi makes a long, unbroken line. I'd choose black or cream merino or a cashmere blend, since both are thin enough to tuck without a ridge at the waistband. Pair it with a wool A-line or pencil skirt in camel or charcoal. Suede ankle boots with a low block heel close the gap between hem and boot. A pendant necklace breaks up the high neckline, which is useful if a turtleneck makes your neck feel short. It's a reliable outfit for gallery visits or lunch with friends on a crisp afternoon.
3. Midi Skirt With Structured Blazer Outfit
A structured blazer over a midi skirt gives you instant authority. Start with a fitted tank or shell, then add a tailored blazer that nips in a little at the waist. Length is where most blazers go wrong over a midi: the hem should stop at the high hip, because a blazer that reaches mid-thigh plus a skirt to mid-calf leaves only a few inches of visible skirt. Black or navy goes with pleated and pencil styles alike. Nude pointed-toe flats lengthen the leg without a heel, and a sleek watch with small hoops is all you need. It goes from a morning meeting to an afternoon at a museum without a change.
4. Midi Skirt With Chunky Sweater and Knee-High Boots
Big sweater, long skirt and tall boots is a cold-weather formula I come back to every winter. Take an oatmeal or cream cable-knit and front-tuck it loosely into a dark wool midi, so the waist still shows. Cable knits add real bulk, which is why that tuck isn't optional. Flat or low-heeled knee-high boots in black or brown leather should disappear under the hem, with opaque tights in the same shade bridging any gap. Finish with a wool wrap coat and a roomy leather tote. Warm enough for weekend errands, and smart enough for a casual dinner.
5. Midi Skirt With Cropped Denim Jacket and Sneakers
A cropped denim jacket might be the ultimate ageless topper, and over a midi skirt it does a specific job. Because it stops at the waist, more of the skirt shows, and your legs read longer. Go for a medium wash over a white or gray cotton tee, with a khaki or olive cotton midi. I avoid pairing a stiff, brand-new denim jacket with a soft skirt; let the denim break in a few washes so the shoulders relax. White leather sneakers, a canvas tote and wayfarer sunglasses make it a Saturday outfit for markets and brunch.
6. Midi Skirt With Silk Blouse and Low-Block Heel Slingbacks
For dressier occasions, I tuck a silk or satin blouse into a black or navy satin-back crepe midi. An emerald or sapphire blouse brings color close to the face, and jewel tones tend to flatter maturing skin more than pastels do. Silk shows every drop of water and perspiration, so I keep a lined or slightly patterned blouse in mind for long, warm evenings. Nude low-block slingbacks give some lift without strain on the ball of the foot. A fine chain, a slim clutch and pearl studs finish it for a wedding reception or anniversary dinner.
7. Midi Skirt With Striped Breton Top and Espadrilles
Stripes on top and a solid skirt underneath is the easy proportion. Choose a navy-and-cream long-sleeve Breton tee in light cotton and tuck it into a relaxed white or navy midi. Horizontal stripes widen whatever they cover, so keep them above the waist and let the plain skirt carry the length. Jute espadrilles, flat or wedge, make it feel like summer, and a straw tote, woven belt and tortoiseshell sunglasses round it out. One caution: white skirts can turn see-through in bright sun, so I always check them against a window first. Good for a seaside lunch or a slow afternoon in town.
8. Midi Skirt With Lightweight Cashmere Sweater and Ballet Flats
A lightweight cashmere sweater in blush or powder blue, loosely tucked into a beige or cream A-line midi, is a soft, quiet outfit. Pastels close to the face can drain color from mature skin, so if blush looks flat on you, try a slightly warmer rose. Matching ballet flats keep it light. Lightweight cashmere pills fastest where a crossbody strap rubs, so I'd carry the quilted bag by its top handle or on the opposite shoulder. A pendant and slim belt complete it for a garden party, a baby shower or a nice lunch out.
9. Leopard Print Midi Skirt With Black Bodysuit and Kitten Heels
Leopard is bolder than it looks on the hanger, and it's far easier to wear than people expect if everything else stays black. Tuck a sleeveless black bodysuit or fitted knit into the leopard midi; a bodysuit is my pick here because it won't creep out of the waistband. Over it, a black blazer or cropped cardigan adds structure. Black kitten-heel slingbacks or pointed pumps lengthen the leg, and gold hoops with a black clutch are enough shine. I'd steer away from leopard that has a high-contrast orange base if you prefer a quieter look. Wear it to a dinner party or the theater.
10. Midi Skirt With Longline Cardigan and Ankle Boots
Worn open, a longline cardigan creates two vertical lines down the body, which is why it's so flattering over a midi. Start with a white or cream tank tucked into a neutral knit skirt, then add the cardigan in gray, oatmeal or camel. Watch the lengths: the cardigan should end either well above or well below the skirt hem, never at the same point, or the outfit looks like one heavy block. Suede ankle boots with a low stacked heel and a slouchy hobo bag keep it relaxed. Great for book club meetings and long coffee catch-ups.
11. Midi Skirt With Linen Button-Front Top and Slide Sandals
This is my hot-weather uniform. A white or natural linen button-front top with rolled sleeves goes over a cotton midi in coral, turquoise or yellow. Linen creases within the first hour, and I tell clients to accept it, because the creases are part of its relaxed look. Flat slide sandals in tan or a metallic finish, a straw bag, a beaded bracelet and big sunglasses finish it. If your upper arms bother you, unroll the sleeves to the elbow rather than switching tops; linen breathes well even at that length. Wear it on a boardwalk or at an outdoor lunch.
12. Wrap Midi Skirt With Fine-Knit Top and Kitten-Heel Mules
Wrap skirts are the most adjustable midi you can buy, and that's why I recommend them so often after 60. The tie lets you set the waist exactly where it's comfortable that day. Pick a solid wrap in wine or forest green and pair it with a slim fine-gauge knit in a neutral, so the fuller skirt has a calm top to balance it. Check the overlap before buying: a skimpy wrap flashes the leg when you sit or walk in wind. Kitten-heel mules give a small lift, and a chain necklace with a top-handle bag makes it right for a brunch or afternoon wedding.
13. Denim Midi Skirt With White Tee and Platform Sneakers
Denim midis can look very modern at 60 when the wash is dark and the distressing is minimal. Look for a hem just below the knee or at mid-calf, and tuck in a clean white crew-neck tee. A slightly cropped tan utility jacket adds warmth without hiding the waist. Denim skirts with a front slit are much easier to walk in than ones with a back vent only, which I check on every pair. Platform white sneakers add height, and a canvas tote with silver jewelry keeps it casual. Wear it for errands, a farmers' market or a casual lunch.
14. Satin Midi Skirt With Cashmere Sweater and Pointed-Toe Pumps
Satin and cashmere together is a texture contrast I love for evenings. The satin skirt has a soft shine, and a relaxed cashmere sweater gives warmth over it. Pick champagne, pewter or navy satin and a sweater in a matching or nearby shade, then do a partial front tuck so the top doesn't look boxy. Satin shows every lump underneath, so I'd wear a smooth slip or smooth shapewear rather than lined tights with a visible waistband. Nude or metallic pointed pumps lengthen the leg and finish the outfit, with pearl drops and a leather clutch for a holiday dinner or gallery opening.
15. Corduroy Midi Skirt With Turtleneck Bodysuit and Leather Loafers
Corduroy adds warmth and texture to a fall skirt without much bulk, as long as you choose a fine or medium wale. Pick tan, rust or olive in an A-line or soft pencil shape. A black turtleneck bodysuit gives a smooth tuck with nothing bunching at the waist. Cognac or black almond-toe loafers and a thin belt in the same leather tie it together, with a structured crossbody and gold hoops. Corduroy flattens and turns shiny if you iron it face down, so I steam it or turn it inside out. Wear it for a foliage walk, a casual workday or a relaxed Thanksgiving gathering.
16. Tiered Midi Skirt With Fitted Tank and Strappy Low Sandals
Tiered skirts add movement and some volume below the waist, which suits women who want more shape through the hip. That fullness needs a simple top, so pair it with a fitted tank or sleeveless knit in white, black or navy. I count tiers before buying: two or three reads graceful, while five or six on a shorter frame can look like a costume. Low strappy sandals in a metallic or neutral shade keep it light, and a beaded necklace, straw clutch and a linen scarf at the wrist add detail. Made for summer garden parties, outdoor concerts and dinners by the water.
17. Pencil Midi Skirt With Crew-Neck Sweater and Oxford Shoes
A pencil midi should skim the body rather than cling, and a little stretch makes it comfortable for a full day. Go for black or charcoal and top it with a light gray or oatmeal crew-neck in a soft knit, half-tucked at the front. Sit down in a pencil skirt before you buy it; if the hem rides up above the knee when seated, it's too narrow. Black leather oxford shoes bring a menswear note that feels unexpected with a skirt. A structured satchel and stud earrings finish it for a casual office day or a lunch in the city.
18. Floral Midi Skirt With Denim Jacket and Ankle-Strap Flats
Florals after 60 look most current on a dark or soft background. A navy, black or blush base with muted blooms is what I look for, rather than bright neon prints. Pair the skirt with a plain white tank or tee and a medium-wash denim jacket cropped at the waist, which keeps the romantic print from looking too sweet. Scale matters too: medium-sized flowers are easier to wear than tiny ditsy prints or giant blooms. Ankle-strap ballet flats keep it comfortable, and a woven crossbody with a charm bracelet suits a spring brunch or baby shower.
19. Monochrome Midi Skirt Suit With Silk Cami
One color from head to toe makes you look taller and instantly put-together. A midi skirt suit in cream, beige or dove gray gives a long line, especially with a fluid silk cami tucked into the skirt and a matching tailored blazer on top. Light neutrals rarely match perfectly across fabrics, so I buy the skirt and blazer as a set, then pick a cami a shade lighter on purpose. Block-heel pointed pumps in the same tone stretch the line further. Gold bracelet, pearl studs and a top-handle bag make it right for weddings and milestone birthdays.
20. A-Line Midi Skirt With Graphic Tee and Minimalist Sneakers
A graphic tee is the fastest way to make a midi skirt casual. Choose an A-line skirt in cobalt, emerald or true red and tuck in a soft vintage-style band tee or a printed top. Soft, worn cotton tucks much better than a new, stiff tee, which tends to balloon out over the waistband. Clean white or cream leather sneakers keep it fresh, and a denim jacket over the shoulders adds a layer for later. A canvas backpack or slouchy crossbody and some fun resin earrings make it a weekend outfit for markets, museums and coffee dates.
Waistbands That Stay Comfortable Through Lunch
Many women tell me they stopped wearing skirts because of the waistband, not the skirt. A rigid band that's fine when you stand can dig in the moment you sit down to eat.
Look for a flat front with elastic at the back only. It looks tailored when your top is tucked and gives you room when you sit. Pull-on knit skirts are comfortable but can roll at the top, so I prefer them with a top worn out or a loose front tuck. If your middle is your fullest part, wear the waistband slightly higher than your belly button, where your torso is narrowest, and choose an A-line or wrap that releases fullness from there.
Tights, Slips and the Rest of What Goes Underneath
What you wear under a midi skirt matters more than what you wear over it. In colder months, opaque tights in the same color as your shoes stretch the leg line, while sheer nude tights can look shiny and dated in photos. Soft, fluid skirts in jersey, satin or thin crepe cling to tights, so a half-slip or a light spray of anti-static on the lining stops the fabric riding up as you walk.
In summer, light cotton or linen skirts often need a slip in sunlight. Hold the skirt up to a sunny window before you wear it out. If you can see your hand through both layers, a skin-tone slip will fix it.
Hem, Fabric and Shoe Come Before Everything Else
If I had to reduce this list to one habit, it would be checking where the hem meets your leg before you think about anything else. After that comes fabric that moves instead of clinging, and shoes you can walk in all day. From a crisp button-down with loafers to a graphic tee with sneakers, every one of these outfits rests on those three choices. Define your waist when it feels good, try a color or print you've been avoiding, and keep the skirts that pass the sit-down test.
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