A size 14 hourglass figure has bust and hips in balance with a clearly smaller waist, and the waist is what I build every outfit around. The real challenge at this size isn't style, it's fit. Ready-to-wear is often cut for a straighter body, so a dress that fits your hips gapes at the waist, or a shirt that fits your waist pulls across the bust. So in each of these 25 outfits, I look for waist definition, a little stretch where it helps, and cuts that skim rather than squeeze. They cover weekends, the office, evenings out and the cooler months, and I've noted the fit point to check on each one.
Why Size 14 Labels Fit Hourglass Curves So Unevenly
Size 14 sits in an awkward spot. In many brands it's the top of the regular range, cut on a pattern designed for a straighter figure and graded up. In others, especially plus ranges that start at 14, the pattern allows more room for bust and hip. That's why one brand's 14 fits beautifully and another's pulls at the bust and gapes at the waist.
When I shop with hourglass clients at this size, I check measurements on the size chart rather than the label, and I compare bust, waist and hip separately. Then I buy for the largest measurement, which is usually bust or hip, and plan to take in the waist. It's worth trying both a regular 14 and a plus 14 or 1X in the same piece; one often fits the curves far better.
Stretch changes the math too. A knit or a woven with a few percent elastane gives an inch or so of ease, so you can often take the smaller size in stretch pieces and the larger one in rigid cotton, linen or non-stretch denim. Check the fabric label before you decide which size to try first.
1. Wrap Dress for Size 14 Hourglass
The wrap dress solves two size 14 hourglass problems at once: the V-neck makes room for a fuller bust, and the tie lets you set the waist exactly where yours is. I'd choose a knee-length or midi in stretch jersey or crepe, which moves without sticking. The thing I check first is the overlap at the skirt. A wrap cut with too little fabric opens at the thigh when you sit, so look for a generous front panel or a faux wrap with a sewn skirt. Nude block heels and a structured crossbody suit brunch, and strappy sandals with gold hoops work for evening. Jewel tones or small prints keep the dress in proportion.
2. High-Waisted Jeans for Size 14 Hourglass
High-waisted jeans only anchor an outfit if they fit at both the waist and the hip, and on an hourglass figure those two numbers rarely match in one standard size. Look for a contoured or curvy waistband, which is cut on a curve to stop the back from gaping, and enough stretch to hold its shape all day without bagging at the knee. Straight-leg and bootcut balance the hip line. Tuck in a stretch-cotton button-down, add a medium leather belt, and finish with white sneakers and a canvas tote for weekends, or ankle boots and a blazer for smart-casual days. Dark denim looks dressier than a mid-wash.
3. Fit and Flare Dress for Size 14 Hourglass
Fit-and-flare is about as close to foolproof as hourglass dressing gets. The bodice follows your shape, the waist seam sits at your narrowest point, and the skirt opens over the hips and thighs, which suits a size 14 hourglass figure well. Cotton poplin and ponte knit hold their shape through the day. The thing that goes wrong most often is a waist seam that sits too high because the bodice is short for a fuller bust, so check the seam lands at your actual waist. Knee length is classic; midi feels more vintage. Low block heels or ballet flats work, and a cropped cardigan ending at the waist covers you in cooler months.
4. Peplum Top and Skinny Jeans for Size 14 Hourglass
A peplum mirrors the hourglass outline: fitted through the bust and ribs, then flaring over the hip. Ponte or a cotton blend holds the flare without the stiffness of scuba fabric. Length matters most here. The peplum should end above the fullest part of the hip, because if it stops right there it adds a horizontal line exactly where you don't need one. A black, navy or jewel-toned peplum top with dark stretch skinny jeans is the classic version. Pointed heels lengthen the leg and statement earrings pull the eye up. Swap your tote for a clutch and it'll go straight from the office to dinner.
5. Belted Blazer Outfit for Size 14 Hourglass
A plain blazer often hangs straight from bust to hem on an hourglass figure, and that boxiness is exactly what you don't want. A belted blazer, or one cut to nip in at the waist, fixes that. Layer it over a silk camisole or fine-knit tank. For a size 14 hourglass, blazers with a bit of stretch or a ponte version are far more comfortable across the bust and back. I always check the button: if it pulls into an X across the front, size up and have the waist taken in. Slim straight-leg trousers in a matching or tonal shade, pointed pumps, layered fine necklaces and a top-handle bag make this an office outfit.
6. Sheath Dress with Belt for Size 14 Hourglass
A sheath without a belt can read as shapeless on an hourglass figure, because it's cut to fall straight past the waist. A substantial belt changes that immediately and gives the clean dress a focal point. Ponte or scuba crepe has enough body to hold its line without clinging. For a size 14 frame, a wide elastic belt is easier to wear than stiff leather, since it moves when you sit. Check the dress at the hip before you buy, because a sheath that's tight there will ride up all day, belt or no belt. Classic pumps and a watch suit the office; metallic heels and a beaded clutch suit cocktails.
7. Crop Top and Wide-Leg Pants for Size 14 Hourglass
Showing a sliver of waist is the most direct way to frame it. A fitted crop top that ends at or just above the waist meets high-waisted wide-leg trousers that skim the hips and flare out. A ribbed knit or double-layer cotton gives support and coverage and won't ride up when you lift your arms. If you'd rather not show skin, choose a crop that just meets the waistband. The trousers want a flat front and some stretch through the hip. Heeled sandals or platform sneakers depending on the plans, a shoulder bag and minimal jewelry finish it.
8. Jumpsuit for Size 14 Hourglass
Jumpsuits can be as flattering as any dress on an hourglass figure, but only if the waist is built in: a wrap style, a belted waist or a seam at the natural waist. A V-neck or surplice neckline makes room for the bust. The fit check I never skip is torso length. Sit down and raise your arms, because a jumpsuit that's short in the body will pull at the crotch and shoulders at the same time, and no belt fixes that. Crepe or jersey with good drape follows your shape. Heeled sandals and a layered necklace work for dinner; flat slides and a denim jacket for daytime.
9. Maxi Dress for Size 14 Hourglass
A maxi dress is easy to throw on, but on a size 14 hourglass the wrong one falls straight from bust to hem and hides the waist entirely. I look for a tie-back empire waist, a wrap maxi or a smocked waist panel instead. Rayon challis and cotton voile drape softly without adding bulk. Lined voile is better if the fabric is pale or sheer in sunlight. A side slit adds movement and makes walking easier. Flat sandals and a wide-brim hat suit summer weekends; wedge espadrilles and gold jewelry dress it up.
10. Pencil Skirt Outfit for Size 14 Hourglass
The pencil skirt follows an hourglass line closely, so it's flattering as long as the fit is right. A high waist sits at your narrowest point, and the skirt should skim the hip and narrow toward the knee. Stretch cotton or ponte gives structure plus room to sit. The side seams are my test: they should run straight down, and if they twist toward the front, the skirt is too tight at the hip. A back vent or slit makes stairs and long strides possible. Tuck in a silky blouse or fine knit, add a slim belt and wear pointed pumps or sleek ankle boots for meetings and presentations.
11. A-Line Midi Skirt for Size 14 Hourglass
An A-line midi skirt is one of the most wearable pieces for an hourglass because it fits at the waist and then gives plenty of room through the hips and thighs. The flare should start right at the waistband. If it starts lower, the skirt hugs the high hip first and the A-line shape is lost. Cotton twill, denim and satin-back crepe all hold the line. Tuck in a fitted crewneck or short-sleeve knit, add a belt if there are loops, and wear ankle boots for cool days or strappy sandals with a straw tote for warm ones.
12. Wide-Leg Trousers for Size 14 Hourglass
Wide-leg trousers add length and movement, and the high waist does most of the shaping. The challenge on a size 14 hourglass is a pair that fits both waist and hip without gaping at the back. A side zip and flat front give a smoother line over the tummy than a front fly. Stretch woven fabrics keep their shape. Tuck in a fine-knit sweater or a cap-sleeve bodysuit to keep the top neat. The high waist often defines things enough on its own; add a slim belt only if the trousers have loops. Heeled sandals or loafers and a structured tote take this from work to dinner.
13. Button-Down and High-Waisted Jeans for Size 14 Hourglass
A tucked button-down with high-waisted jeans is the most reliable casual formula I know for an hourglass figure. The problem is always the buttons across the bust. If you see gaps between them, either size up and have the waist taken in, or look for shirts with hidden snaps at the bust line or a stretch-cotton weave. High-rise straight or bootcut jeans with a contoured waistband give the shape. Roll the sleeves, add a leather belt and finish with loafers, ballet flats or white sneakers. A pendant and a structured tote work for errands and casual Fridays.
14. Slip Dress with Blazer for Size 14 Hourglass
A satin slip under a tailored blazer pairs something fluid with something structured, and on an hourglass figure that contrast does a lot. The slip should be bias-cut, meaning cut on the diagonal of the fabric, so it drapes over curves rather than clinging. Satin does show everything underneath, so smooth underwear and a slip are worth it. The blazer should fit at the shoulders and nip at the waist, either belted or with a single button. Strappy heels and a mini bag suit evening; pointed mules suit a dinner date. Emerald, sapphire or burgundy satin looks especially rich against a neutral blazer.
15. Corset Top Outfit for Size 14 Hourglass
A corset-style top puts the hourglass waist front and center. Modern versions use flexible boning and stretch panels, so they shape without restricting, which makes them wearable for an evening. On a size 14 frame, wide straps carry the weight of a fuller bust far better than thin ones, and a lace-up or hook-and-eye back lets you adjust the fit. Sit down in it before you buy; boning that digs in at the hip when seated will be uncomfortable all night. A black or neutral corset with high-waisted wide-leg trousers or a matching maxi skirt, heeled sandals, layered chains and a sleek clutch make it a party outfit.
16. Two-Piece Set for Size 14 Hourglass
A matching set makes planning easy and reads as one long column of color. For an hourglass, the waist is still the deciding factor: the top should end at the natural waist and the bottom should rise high enough to meet it, with no gap and no overlap at the hip. A fitted crop or wrap top with a high-waisted midi skirt or wide-leg trousers both work. Ribbed knits, linen blends and satin-finish sets all wear well. Flat sandals and a canvas tote suit a vacation; heeled mules and a mini bag suit rooftop drinks. You also get two separates to wear with the rest of your wardrobe.
17. Bodysuit and High-Rise Jeans for Size 14 Hourglass
A bodysuit is the cleanest way to tuck, since there's no fabric bunching at the waistband and nothing to readjust all day. On a size 14 hourglass, I look for adjustable straps and a V-neck or square neck that makes room for the bust. Check the torso length, because too short a body and it pulls at the shoulders. Pair it with high-rise straight or bootcut jeans that fit easily through the hip and thigh, and the waist shows without any effort. A statement belt, ankle boots and a cropped jacket or long cardigan cover weekends and casual dates.
18. Trench Coat and Dress for Size 14 Hourglass
A trench coat almost always has a built-in belt, which is why it suits hourglass figures so well. The catch on a size 14 frame is the double-breasted front, which adds fabric across the bust, so I'd choose a lightweight trench and leave the top buttons open. Layer it over a fitted ribbed-knit or jersey wrap midi. Tie the belt at your natural waist rather than leaving it hanging, and knot it at the side rather than buckling it so it looks softer. Wear it with knee-high boots or pointed pumps and a leather satchel for work and in-between weather.
19. Cardigan and Cami for Size 14 Hourglass
An open longline cardigan draws two vertical lines down the body and frames the waist between them, which lengthens an hourglass figure. Choose a fine-gauge knit, as a chunky one adds width at the hip where the cardigan ends. Underneath, a silk or stretch cami tucks into high-waisted skinny jeans or slim trousers. The cardigan should end below the widest part of the hip, not at it. A long pendant follows the same vertical line, and ballet flats or low block heels keep it comfortable for casual office days and coffee dates.
20. Off-Shoulder Top and Pencil Skirt for Size 14 Hourglass
An off-shoulder top shows the collarbones and shoulders, and with a pencil skirt it traces the whole hourglass outline. For a size 14 frame, wide elastic at the neckline that sits on the upper arm, not the bicep, stays in place and doesn't dig in. Strapless or convertible bra support makes all the difference here. The top should end at the natural waist, then tuck into a high-waisted stretch pencil skirt. Heels and a clutch suit a dinner date; flat slides and a crossbody keep it casual. Two solid colors look the most streamlined.
21. Knit Midi Dress for Size 14 Hourglass
A knit midi is my favorite cool-weather dress for an hourglass, as long as it has a waist: a built-in waistband, a self-tie belt or a body-skimming fit. Ribbed knits cling more than sweater knits, so if you'd rather not show every line, choose a thicker gauge. Knits also pill at friction points like under the arms and where a bag rubs, so a quick pass with a fabric shaver keeps them looking fresh. A V-neck or scoop neckline is most flattering. Knee-high boots and a wool coat for winter, ankle boots and a leather jacket for fall. Camel, charcoal, burgundy or forest green all work.
22. Tailored Shorts Outfit for Size 14 Hourglass
Tailored shorts can look as polished as trousers, and on an hourglass figure the high waist and flat front do most of the work. I aim for a mid-thigh length, which feels secure without looking too long, and check that the hem doesn't ride up into the inner thigh when walking; a bit of stretch helps. Tuck in a light button-down or a breezy cap-sleeve blouse, add a slim leather belt and finish with flat sandals or espadrilles. A straw tote and big sunglasses suit a vacation, and a blazer over the shoulders makes it dinner-ready. Linen, cotton twill or crepe in a neutral works with most tops.
23. Leather Jacket and Midi Dress for Size 14 Hourglass
A leather jacket over a soft midi dress gives you a mix of tough and pretty, and the jacket length decides whether it works on an hourglass. It should end at the natural waist; a longer, hip-length jacket covers your shape and adds width. Underneath, choose a dress with a defined waist, a wrap, a belted fit-and-flare or a smocked waist. New leather is stiff across the shoulders and softens with wear, so give it time before judging the fit. Ankle boots with a small heel and a crossbody suit fall and spring weekends. Black or brown leather goes with almost any dress.
24. Denim Jacket and Maxi Dress for Size 14 Hourglass
A denim jacket over a maxi dress is a comfortable casual outfit, and on an hourglass it only works if the jacket stops at the waist. A cropped cut keeps the waist visible, and a standard jacket can cover it. Choose a maxi with a fitted bodice and a defined waistline, whether button-front, wrap or smocked. Denim with a little stretch is easier across the bust and arms. Flat sandals or white sneakers, a canvas tote, rolled sleeves and a simple pendant make it a market or lunch outfit. Light-wash denim suits spring and summer; dark wash carries into fall.
25. Belted Shirt Dress for Size 14 Hourglass
A shirt dress gives you the structure of a button-down in one piece, and the button placket draws a long vertical line. On a size 14 hourglass, the same issue as with shirts applies: buttons can gape at the bust, so fit that first and use the belt to take in the waist. Cotton poplin or a soft cotton blend works, with a self-tie or leather belt at the natural waist. Knee or midi length both work. Rolled sleeves with flat sandals or white sneakers for daytime; heeled mules and a structured bag for the office. Khaki, olive, navy or a fine stripe are easy colors.
Bust Gaps, Back Gaps and the Alterations That Close Them
Most of the outfits above assume the clothes fit the waist, and off the rack that rarely happens on an hourglass figure. These are the fit problems I see most and how a tailor usually handles them.
- Jeans and trousers gaping at the back waist: the tailor takes in the center back seam. It's quick and inexpensive in most cases.
- Shirts gaping between buttons: buy the size that fits the bust, then have darts added at the back waist so the shirt doesn't billow.
- Dresses fitting the hips but loose at the waist: side seams can be taken in at the waist only, tapering back out at the hip.
- Blazers pulling at the button: there's usually no fix if the bust is too tight, so size up and have the waist shaped instead.
- Wrap dresses gaping at the neckline: a small hidden snap or a stitch where the fabric crosses holds it in place.
Alteration costs vary by area and garment, but simple waist and dart work tends to be among the cheaper jobs. I'd rather spend on that once than wear something that pulls every day.
Your Waist Is the Reference Point for Every Outfit Here
You don't need a closet of specialty pieces to dress a size 14 hourglass. You need to know which cuts follow your shape and make sure the waist is defined. Wraps, high-waisted bottoms, belted layers and fit-and-flare dresses keep working because they follow your shape. Choose fabrics with comfortable stretch and buy for the bust and hip first, then fix the waist. Use these outfits as a starting point and adapt them to your own style and season.
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