Dressing well in your 40s and beyond is less about chasing trends and more about finding clothes that feel good, fit comfortably, and make you excited to get dressed. If you fall into the midsize range—somewhere between straight sizes and plus—you know the frustration of loving a piece on the hanger but feeling like it just doesn’t sit right. The key to successful midsize outfits for women over 40 is striking a balance between ease and structure, while honoring your shape instead of hiding it. The thirty-five head-to-toe looks ahead are built around real-life bodies, real comfort needs, and the kind of low-effort polish that makes mornings easier. Each outfit combines current style with the movement and breathability a midlife body appreciates, so you can feel like the most pulled-together version of yourself without wrestling with your clothes all day.
1. Straight-leg jeans with a tucked-in blouse and loafers
This is the reliable weekday uniform that never lets you down. A dark-wash straight-leg jean with just enough stretch sits smoothly through the hips and thighs without pinching, while a soft button-front blouse in white or cream adds an instant touch of polish. Tucking the blouse in fully or doing a loose front tuck defines your waistline without feeling fussy. On the feet, a classic leather loafer in black or tortoise keeps the look grounded and walkable for all-day errands or casual office days. Add a slim leather belt that sits at your natural waist, and finish with a medium-sized structured crossbody bag. This outfit works because the proportions stay balanced—the fitted top and straight leg create a long, clean line that flatters without clinging anywhere you don’t want it to.
2. Midi slip dress with a denim jacket and white sneakers
A silky midi slip dress might feel intimidating at first, but layering it with a cropped denim jacket completely changes the vibe. The jacket adds structure across your shoulders while the bias-cut dress drapes softly over the midsection—no waistband digging in, no restrictive seams. Stick to solid neutrals like champagne, olive, or navy for the dress, then throw on a light-wash jacket for contrast. Clean white leather sneakers keep the look firmly in casual territory and make it walkable for weekend coffee runs or casual dinner plans. A delicate gold pendant necklace draws the eye upward and breaks up the expanse of fabric. This is the kind of outfit that looks intentional and current without trying too hard, and the adjustable jacket lets you control coverage depending on how you feel that day.
3. Wide-leg linen trousers with a tank top and sandals
When the weather warms up, nothing beats the breezy ease of wide-leg linen trousers. High-waisted with a relaxed fit through the leg, they offer maximum airflow and zero thigh cling—a genuine win for midsize bodies. Tuck in a ribbed cotton tank top in a tonal shade like oatmeal, terracotta, or dusty blue, and let the fabric gently skim your torso without squeezing. On your feet, flat leather slide sandals or a low stacked-heel sandal add just enough lift to keep the trousers from dragging. A woven tote bag and oversized tortoiseshell sunglasses play up the effortless vacation energy. This outfit relies on natural fibers that let your skin breathe, and the uninterrupted column of color from the tank into the trousers creates a lengthening effect that looks graceful on every height and shape.
4. Wrap dress with espadrille wedges and a straw tote
A true wrap dress is a gift for midsize proportions because you control exactly how much fabric wraps around your waist and bust. Look for a midi length in a stretch jersey or a lightweight linen blend—something with a little give that moves with you. A small floral print or a solid jewel tone like emerald or ruby brings warmth to your complexion without overwhelming your frame. Espadrille wedges add height in a stable, walkable way and echo the dress’s easy femininity. Carry a structured straw tote for the farmer’s market or a garden party, and add a slim gold bangle for a quiet touch of shine. The V-shaped neckline and adjustable tie draw the eye inward and upward, creating an hourglass effect that feels supportive without any underwire or shapewear required.
5. High-waisted trousers with a bodysuit and pointed-toe flats
Sometimes you want a completely smooth, tucked-in look with no fabric bunching at your waistband. Enter the stretch bodysuit. A scoop-neck or square-neck bodysuit in a substantial matte jersey paired with high-waisted tailored trousers creates a streamlined column shape that’s both office-ready and coffee-date friendly. Choose trousers in a fluid crepe or lightweight suiting fabric that drapes instead of clings. Pointed-toe ballet flats in a matching neutral tone extend the line of your leg without the foot pain of heels. A long pendant necklace and a sleek leather tote finish the ensemble with quiet sophistication. This combination hugs where you want support and floats away from the midsection, giving you the cleanest possible silhouette.
6. Maxi skirt with a graphic tee and leather sandals
An easy way to bring personality into a simple warm-weather look is pairing a graphic tee with a flowy maxi skirt. The tee should be soft and slightly relaxed—not too boxy and not too tight—and the skirt should have an elastic or adjustable waist for all-day comfort. Tuck the front of the tee to show the waistband, then let the skirt fall in soft folds. Choose flat leather sandals with a bit of hardware for an edge, and carry a canvas tote or a crossbody bag. The contrast between the casual top and the elegant movement of the skirt creates an approachable tension that reads modern and a little artsy. This outfit celebrates individuality and works beautifully for brunch, casual galleries, or an afternoon walk.
7. Blazer and tailored shorts with a camisole and heeled mules
Tailored shorts in a longer, Bermuda-length cut offer coverage while still feeling cool in warm months. Pair them with a lightweight single-breasted blazer in a matching neutral tone, then layer a simple silk or satin-finish camisole underneath. The blazer brings structure to your shoulders and arms, while the silky cami stays soft against your skin. Slip-on heeled mules in a coordinating shade keep the leg from looking cut off and add just enough height to feel polished. A slim clutch or small structured shoulder bag and a layered chain necklace complete the look. This combination works for elevated casual events, rooftop gatherings, or dinner with friends—you get the polish of a suit set without the heaviness of full-length trousers.
8. Wide-leg jumpsuit with a belt and block-heel sandals
A wide-leg jumpsuit is a complete outfit in one piece, and when the proportions are right, it can be extremely flattering on a midsize frame. Look for a style with a defined waist—either stretch-smocked or cinched with a self-tie belt—and a V-neckline that opens up the chest. The wide legs balance out the torso and create a long vertical line. Add your own belt in a contrasting material like woven leather or metal chain to personalize it further. Block-heel sandals give you stable lift and peek out just slightly from under the hem. A bold cuff bracelet or a set of slim bangles adds a finished touch. This outfit goes from desk to dinner seamlessly and packs like a dream for travel.
9. Button-down shirt dress with a belt and white sneakers
A crisp shirt dress is a warm-weather workhorse that flatters almost every midsize shape because of the vertical line created by the button placket. Choose a cotton poplin or lightweight chambray that holds its shape without stiffness, and cinch it with a belt at your natural waist to break up the length. Roll the sleeves to just below the elbow for a relaxed, capable feel. White low-profile sneakers balance the polish of the shirting fabric and keep things practical for a full day on your feet. A canvas belt bag worn crossbody or a simple backpack adds modern utility. This outfit feels fresh, put-together, and completely effortless—perfect for school pickup, casual Fridays, or a weekend museum trip.
10. Pleated midi skirt with a cashmere sweater and ankle boots
For cooler days, a pleated midi skirt brings fluid movement that feels elegant and forgiving through the belly and hips. An elastic waistband helps it sit comfortably at your narrowest point without digging. Tuck in a lightweight cashmere or merino wool crewneck sweater for warmth that doesn’t add bulk, and let the pleats move freely below. Low-heeled ankle boots in a neutral suede or leather anchor the look and keep it appropriate for work or lunch. Add a slim leather watch and a structured top-handle bag. The textural contrast between the soft knit and the swishy pleated fabric creates visual interest, while the covered-up top balances the volume of the skirt for a silhouette that feels proportional and modern.
11. Faux leather leggings with an oversized sweater and combat boots
Faux leather leggings might sound like a young trend, but styled the right way, they can be a sleek, edgy base layer for a 40-plus wardrobe. Choose a high-waisted pair with a thick, matte-coated finish. On top, a chunky oversized sweater in a neutral tone—charcoal, oatmeal, heather navy—covers the hips while the leggings define the leg. Lace-up combat boots in black leather ground the outfit with a bit of toughness. A long pendant necklace or a metallic chain bag adds a touch of polish. The volume contrast here is key: the roomy sweater provides soft coverage while the slim leggings and substantial boots keep your lower half looking streamlined and intentional. Throw on a beanie or a wool fedora for extra personality.
12. Cropped wide-leg pants with a puff-sleeve top and mules
Celebrating your shape sometimes means playing with volume in fun ways. Cropped wide-leg pants in a structured cotton twill hit just above the ankle, showing off a bit of skin or a fun sock choice. A puff-sleeve blouse or top with a subtle shoulder balloon adds feminine shape up top without overwhelming your frame—just make sure the body of the top stays relatively fitted or tucked in. Slip-on mules with a low block heel slide on easily and keep the ankle line clean. Small gold hoop earrings and a boxy mini bag add contemporary polish. The proportions work because the volume is distributed between the sleeve and the pant, leaving your waist defined and your overall silhouette balanced rather than swallowed.
13. Denim midi skirt with a striped tee and ballet flats
A denim midi skirt in a dark indigo wash feels nostalgic in the best way and sits comfortably through the hips. An A-line or slightly flared cut gives your legs room to move without adding width. Tuck in a classic navy-and-cream striped long-sleeve tee—Breton stripes have a timeless, almost French effortless quality that flatters every age. Simple leather ballet flats with a tiny bow or metal accent keep the silhouette light and feminine. A thin red lip and a basket bag nod to classic Parisian street style in a subtle, wearable way. This outfit feels cheerful without being sugary and works for everything from casual business meetings to Saturday errands. The vertical stripes and deep denim work together to elongate.
14. T-shirt dress with a utility jacket and sneakers
A good T-shirt dress in a midi length gives you the comfort of your favorite tee in a shape that reads as a purposeful outfit. Choose one with a slight cocoon shape or side slits for easy movement. Layer an olive or khaki utility jacket over it to add structure through the shoulders and a defined waist when you button or belt it. White court sneakers keep the whole look grounded and walkable. Throw on a baseball cap and a canvas backpack for an active day, or switch to delicate jewelry and a leather crossbody to dress it up slightly. The best thing about this outfit is the way the jacket provides coverage and shape over the softer dress underneath, making it feel secure and stylish for unpredictable weather and long outings.
15. Culottes with a sleeveless blouse and block-heel sandals
Culottes—those wide, cropped pants that almost mimic a skirt—are a midsize secret weapon. They give you the ease and airflow of a skirt with the security of pants. Look for a pair in a drapey fabric like Tencel or rayon that moves fluidly when you walk. Pair them with a sleeveless blouse in a silky fabric that you can tuck in loosely, and add block-heel sandals for a bit of height. Gold accessories—a stack of thin bracelets, a simple chain anklet—pick up the warm tones and add shine near your face. The silhouette is intentionally voluminous on the bottom and slim on top, which draws attention upward and creates a modern, art-gallery-ready proportion that feels fresh and sophisticated without any constriction.
16. Paper bag waist trousers with a tucked-in tank and wedges
Paper bag waist trousers cinch at the smallest part of your waist and then soften through the hips, which makes them incredibly flattering for midsize shapes that carry weight through the middle. The tied belt detail provides natural waist definition without any tight elastic. A fitted ribbed tank tucked in keeps the look simple and lets the trousers be the focal point. Choose neutral earthy tones like sand, clay, or olive. Espadrille wedges or woven-platform sandals add height and texture, and a minimal leather tote keeps the outfit practical. This look is polished enough for a creative office but relaxed enough for brunch outside. The high waist and soft fold-over detailing create a gentle hourglass suggestion without any restrictive shapewear underneath.
17. Long cardigan over a tank and skinny jeans with ballet flats
For days when you want the equivalent of a wearable hug, a longline cardigan in a soft knit draped over a simple tank and skinny jeans delivers. Choose a cardigan that hits mid-thigh or lower to create a long vertical column that flatters your entire frame. Dark-wash skinny jeans with a bit of stretch hold you in gently, and a form-fitting tank in white or black acts as the anchor underneath. Slip on a pair of soft leather ballet flats in a blush or metallic tone for a barely-there feminine finish. A long beaded necklace or a lightweight patterned scarf adds personality near your face. This outfit is ideal for air-conditioned offices, travel days, or any time you need to feel comfort-first while still looking intentional.
18. Boho maxi dress with a wide-brim hat and ankle boots
A printed maxi dress in a lightweight rayon or cotton voile brings effortless boho romance to any season. Look for one with a smocked or elasticated waist that gives shape without tightness, and a tiered skirt that moves beautifully when you walk. A wide-brim felt hat adds mystery and protects your face from the sun. Suede ankle boots with a low stacked heel ground the floatiness of the dress and make it suitable for transitional weather. A fringe crossbody bag and layered turquoise or beaded bracelets lean into the free-spirited vibe without costume-y excess. This outfit is perfect for a vineyard visit, an outdoor concert, or a vacation walkaround. The combination of soft fabric and structured accessories keeps the look balanced and intentional.
19. Sweater vest over a button-down and straight-leg jeans with loafers
Sweater vests aren’t just for prep school anymore—they’ve come back as a clever layering tool that adds warmth and structure without the bulk of a full jacket. Layer a fine-knit V-neck sweater vest in cream or camel over a crisp white button-down shirt. The collar and cuffs peeking out create a neat, intelligent vibe. On the bottom, wear medium-wash straight-leg jeans with a raw hem for a modern edge. Loafers in a rich oxblood or tortoise finish tie everything together, and a slim leather belt keeps the waist defined. This outfit nails the smart-casual dress code and works wonderfully for casual office days, parent meetings, or a book club gathering. The vest also provides a vertical line through your center that lengthens the torso.
20. Denim jacket over a floral midi dress and white sneakers
Combining a floral midi dress with a denim jacket is the ultimate in feminine-meets-tomboy balance, and it works across all seasons. Choose a dress in a darker floral—think navy, burgundy, or deep green blooms on a muted background—for a more sophisticated feel. The denim jacket should hit right at your waist or hip to reinforce your natural shape. White sneakers keep the whole look fresh and walkable for long days. A small leather bucket bag and a pair of oversized sunglasses add a cool, model-off-duty ease. The beauty of this outfit is how the jacket provides shoulder structure while the soft dress drapes over any midsection concerns. You can easily remove the jacket when you want more airiness or tie it around your waist for a different proportion.
21. Trench coat over a turtleneck and wide-leg trousers with pumps
A classic trench coat is the ultimate transitional layering piece, and it pulls together any outfit instantly. Wear a lightweight cashmere or ribbed cotton turtleneck as your base layer, tucked into high-waisted wide-leg trousers in a wool blend or crepe. The turtleneck frames your face and neck elegantly, while the trousers create a long, unbroken line from waist to floor. A sleek pointed-toe pump in a neutral tone adds polish without sacrificing stability. Carry a structured leather satchel and a printed silk scarf tied around the handle or your neck. This outfit is professional and timeless, appropriate for important meetings, dinner events, or any occasion where you want to feel powerful and graceful at the same time.
22. Quilted vest over a flannel shirt and straight-leg jeans with lug-sole boots
For crisp autumn weekends or casual outdoor gatherings, a quilted vest layered over a soft flannel shirt provides lightweight warmth without overheating. The vest adds an outer layer of structure while leaving your arms free to move. Tuck the flannel into high-rise straight-leg jeans and add a pair of lug-sole ankle boots for a little height and a lot of practicality. A knit beanie and a canvas crossbody bag finish the look with outdoorsy charm. This outfit works because the vest visually narrows your torso while the flannel shirt peeking out at the collar and cuffs adds approachable softness. The boots ground the silhouette and keep you steady on uneven terrain—ideal for a pumpkin patch, farmers market, or a walk through leaf-strewn trails.
23. Puffer jacket with a knit dress and knee-high boots
Cold weather doesn’t mean giving up on feeling feminine. A lightweight but warm puffer jacket in a glossy finish or a rich jewel tone worn over a fitted knit midi dress strikes the perfect balance between practical warmth and sleek shape. The dress should have some stretch and a bit of ribbing through the middle to provide gentle definition. Knee-high leather boots with a low block heel continue the vertical line and keep your legs warm. Add a cozy knit scarf and a pair of leather gloves for extra polish. The puffer jacket adds just enough volume up top that the fitted dress underneath feels intentionally sleek by contrast. This outfit is wonderful for a winter dinner date, city shopping trip, or a holiday lights walk.
24. Faux fur coat over a slip dress and heeled boots
A faux fur coat instantly elevates even the simplest outfit into something glamorous. Layer a soft, plush jacket in a neutral tone like camel, charcoal, or ivory over a simple slip dress in a complementary shade. The juxtaposition of rich, textured outerwear and a sleek, barely-there dress creates a gorgeous balance between coverage and sensuality. Heeled ankle boots with a pointed toe add sophistication and elongate the leg. A clutch or a small chain-strap bag keeps your personal items close without disrupting the lines. Delicate drop earrings and a swipe of bold lipstick complete the look for an evening event where you want to feel special. The coat also provides arm and back coverage while the dress skims over the midsection without restriction.
25. Wool blazer over a cashmere sweater and tailored trousers with loafers
A well-cut wool blazer is a cornerstone of a grown-up wardrobe, and when paired with soft separates, it offers structure without stiffness. Choose a single-button blazer in a dark neutral like navy, charcoal, or chocolate, and layer it over a lightweight cashmere crewneck. The trousers should be tailored but not tight—a straight or slightly tapered leg in a coordinating tone works beautifully. Leather penny loafers in a polished finish add a menswear-inspired twist that feels modern. A watch with a leather strap and a pair of small diamond or pearl studs bring quiet elegance. This outfit can walk into a boardroom or a gallery opening with equal confidence and provides full coverage through the arms and torso while the knit underneath remains breathable and soft.
26. Corduroy pants with a chunky sweater and shearling-lined boots
Corduroy has a soft, vintage texture that immediately signals cozy cool weather. A straight-leg or slightly wide-leg cord pant in a warm caramel, rust, or olive shade pairs beautifully with a chunky knit sweater in a complementary cream or oatmeal. Tuck just the front of the sweater to hint at your waist without bulk. Shearling-lined ankle boots or chukka boots keep your feet toasty and add a nice rugged contrast to the refined texture of the cord. A leather hobo bag and a wide knit headband complete the warm, grounded energy. The thickness of the sweater balances the structure of the pants, and the boot height prevents the wide leg from feeling too heavy. This outfit is perfect for bonfires, cozy dinners, or browsing a holiday market.
27. Sweater dress with opaque tights and over-the-knee boots
When the temperature drops, a sweater dress becomes your one-and-done hero piece. Look for a midi-length style with a subtle side slit or a cable knit texture that adds visual detail without bulk. Opaque black or charcoal tights underneath smooth your leg line and provide warmth, while flat or low-heeled over-the-knee boots add warmth and a modern edge. A wide leather belt worn at the waist creates shape over the knit fabric. Add a long pendant necklace that echoes the vertical line. This outfit is effortlessly pulled together and incredibly comfortable—ideal for a winter dinner party, a show, or even a casual holiday gathering where you want to feel chic and warm.
28. Poncho with leggings and riding boots
A poncho is a beautiful alternative to a structured coat and drapes in a way that feels artistic and forgiving on a midsize frame. Choose a substantial knit poncho in a neutral tone like heather gray or camel with fringe or ribbed detailing. Underneath, wear a simple long-sleeve fitted top and high-quality ponte leggings that hold their shape. Tall riding boots in flat leather with a slight heel add a classic, equestrian polish. A crossbody bag and a felt fedora bring a touch of bohemian sophistication. The poncho creates a striking A-line silhouette that provides coverage for the midsection while the leggings and boots keep the lower half sleek and streamlined. It’s a wonderful look for casual winter outings when you want to feel wrapped up and stylish.
29. Velvet blazer with dark jeans and ankle boots
For an evening out when you want to look festive without being overly dressy, a velvet blazer is your best friend. The soft, light-catching texture feels special and luxurious, while the tailored cut provides shoulder structure. Wear it over a simple black or ivory camisole and dark-wash skinny or straight-leg jeans. Ankle boots in black suede with a sleek pointed toe keep the look appropriate for night. A jeweled statement earring or a layered necklace draws attention up toward your face. The richness of the blazer against the simplicity of the jeans strikes an ideal balance between dressed-up and approachable. This outfit is a go-to for concerts, birthday dinners, or gallery openings where you want to feel polished but not overdressed.
30. Plaid trousers with a solid turtleneck and oxford shoes
Menswear-inspired plaid trousers bring pattern and personality to your lower half while a solid turtleneck in black, ivory, or a coordinating tone keeps the look anchored and chic. Choose trousers with a straight or slightly wide leg in a wool blend for structure and warmth. Tuck the turtleneck in smoothly, and add a slim leather belt. Classic oxford shoes or brogues lean into the preppy, intellectual vibe, and a leather satchel or structured backpack completes the look. This outfit has a collegiate sophistication that reads well for creative offices, lectures, or afternoon tea. The vertical stripe of the plaid elongates, and the turtleneck visually lifts the neck and jawline—a classic combination that feels both smart and comfortable on the body.
31. Chambray shirtdress with a belt and ankle boots
A chambray shirtdress has the easy, throw-on appeal of denim but in a softer, more breathable form. A midi length with long sleeves you can roll up gives year-round versatility. Cinch the waist with a brown leather belt to create an hourglass effect, and add suede ankle boots in a taupe or caramel tone for a warm, rustic feel. A leopard-print hair scarf or a simple gold necklace adds just the right amount of personal detail. This outfit is a perfect bridge between casual and put-together, great for lunch with friends, a creative workplace, or even a casual date night. The belt ensures the dress doesn’t overwhelm your shape, while the boots give you a comfortable, steady stride.
32. Cotton maxi dress with a cropped cardigan and sandals
A sleeveless cotton maxi dress in a solid color or subtle stripe is the backbone of a hot-weather wardrobe. The maxi length offers sun protection and elegant movement, while the cotton or linen blend keeps you cool. Throw a cropped cardigan over your shoulders for shoulder coverage that won’t add bulk—a cap-sleeve or short-sleeve style works best. Flat leather sandals with a bit of metallic detail add sparkle without lift. A straw visor or wide-brim hat and a woven market basket complete this sun-ready look. The cropped cardigan stops above your waistline, which highlights your narrowest point while covering the upper arms. This outfit transitions from a morning market trip to an alfresco lunch with zero adjustments needed.
33. Linen-blend suit with a camisole and heeled sandals
A matching linen-blend blazer and trouser set in a soft neutral like stone, sage, or blush feels modern, refined, and completely breathable. The blazer can be worn open over a simple silk or rayon camisole for a hint of sheen at the neck. The trousers should sit at the natural waist and fall to a wide or straight leg. Heeled sandals with a block heel or a sleek ankle strap add feminine shape to the bottom. Gold jewelry—a simple chain, a cuff—catches the light against the natural texture of the linen. This suit-alternative is ideal for summer weddings, garden parties, or high-end brunches where you want to look polished without the weight of traditional suiting.
34. Sequin top with black jeans and pointed-toe heels
For occasions that call for a little sparkle, a sequin or metallic knit top worn with black jeans keeps the look grounded and sophisticated rather than costume-like. Choose a top in a relaxed fit—perhaps a boatneck or a slightly slouchy silhouette—so the sequins don’t feel tight or scratchy. Black high-waisted jeans in a slim or straight cut streamline the lower half. Pointed-toe heeled pumps in black suede or a metallic finish elongate the leg and add dressiness. A sleek clutch and a pair of chandelier or linear drop earrings complete the ensemble. The combination of sparkle-on-top and simplicity-on-bottom is a formula that works for cocktail parties, dinner celebrations, or New Year’s Eve without any fussy silhouettes.
35. Satin midi skirt with a tucked-in sweater and heeled boots
A satin midi skirt in a rich color like plum, forest green, or bronze adds lustrous movement and a touch of evening elegance. Tuck in a lightweight cashmere or fine-gauge merino sweater in a matching or tonal shade—this creates a monochromatic column that’s incredibly lengthening. Heeled ankle boots in black or metallic leather complete the refined silhouette. A velvet or beaded clutch and a pair of elegant drop earrings pull the look into special-occasion territory. The smooth satin fabric glides over the hips and thighs without clinging, while the sweater provides soft structure through the torso and arms. This outfit epitomizes effortless evening dressing for a woman who wants to feel comfortable, confident, and radiant.
Conclusion:
Building a midsize wardrobe after 40 is an act of self-knowledge and self-respect. The 35 looks here aren’t about hiding your body or chasing someone else’s version of stylish—they’re about wearing clothes that honor your curves, your comfort, and the life you actually live. The common thread is balance: structure on top when you want coverage, softness through the middle for ease, and proportions that work together to create long, clean lines. Pay attention to fabrics that move, waistlines that don’t fight you, and footwear that truly supports a full day on your feet. When you stop dressing for a size tag and start dressing for how you want to feel, getting dressed becomes a pleasure again. Trust your instincts, edit relentlessly, and enjoy the confidence that comes from wearing what works.
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