A wide brim hat does two jobs at once: it shades your face and gives an outfit a clear focal point. People tell me they love hats but never know what to wear under them, and the answer is usually less than they think. From an oversize floppy straw style at the beach to a structured wool fedora on a cold fall morning, the brim is already the loudest thing you're wearing, so the clothes should support it. The thirty outfits below run from denim and tanks to slip dresses and trench coats, and for each one I've noted what I'd check about the hat itself, because brim width, crown shape and material matter as much as the clothes.
Matching Brim Width to Your Height and Shoulders
The hat that suits you most is about proportion more than face shape. I compare the brim to the width of your shoulders. When the brim reaches past them, the hat dominates. When it sits just inside, it frames you. Most fedoras and boaters fall around two and a half to three and a half inches of brim, while floppy sun hats often go to four or five.
- Petite frames: a medium brim and a lower crown, or the hat swallows you.
- Tall or broad-shouldered: wide brims and taller crowns balance well.
- Round or full faces: a crown with some height and an angled, slightly tilted brim adds length.
- Long or narrow faces: a lower crown and a wider, flatter brim add width.
Getting the size right
Measure around your head just above the ears and across the middle of your forehead, where the hat will sit. A hat that's too tight leaves a red line and gives you a headache. One that's too loose lifts in the first breeze. Self-adhesive foam sizing tape inside the sweatband can tighten a hat that's slightly too big. A hat that's too small rarely stretches by much.
1. Wide brim straw hat with linen dress
A midi linen shift in white, oatmeal or sage under a raffia or Panama-style straw hat is the easiest hat outfit I know. Every piece breathes, so you stay cool, and the natural textures of linen, straw and a woven tote belong together. Flat tan or cognac sandals keep it grounded, and slim oval sunglasses sit under the brim without crowding it. I match the hat to the dress in tone so the outline stays soft. It's my go-to for a market run or a coastal weekend.
2. Wide brim fedora with blazer and trousers
Felt and tailoring go together because both hold a crisp line. A structured wool or felt fedora over a fitted turtleneck, a single-button blazer in cream, camel or charcoal and straight trousers that graze the top of the foot turns office separates into something people notice. Pointed leather ankle boots, a fine chain and small hoops are plenty. With a strong blazer shoulder, I keep the brim moderate, around three inches, so the hat matches the shoulder line instead of overpowering it. Remember the etiquette for long lunches: most people take a hat off indoors at the table.
3. Wide brim hat with floral maxi dress
A floral maxi can drift into sweet; a solid felt or straw hat in an earthy color gives it a firm edge. I pick the hat color from the print, rust, camel or olive, so it looks planned. A small-to-medium floral with a defined waist keeps the volume tidy under a big brim. Flat suede sandals or low block mules and a slouchy leather crossbody finish it for a garden party or daytime wedding. Let your hair fall in loose waves under the brim; tight updos make a wide hat look perched.
4. Wide brim hat with denim shorts and tank top
A plain base is what lets a dramatic brim work. High-waisted light-wash denim shorts and a ribbed tank in cream, black or espresso keep it clean, and the bare legs balance the visual weight up top. Flat sandals or white sneakers, a canvas tote, gold hoops and a woven belt with a slight western note. On a breezy day, a floppy straw brim with no chin cord ends up in your hand; I look for a hat with an inner elastic band or add one.
5. Wide brim hat with black slip dress and heels
A black satin or silk bias-cut midi slip with a black felt fedora or boater is my fastest route to an evening look that feels finished. The slip is soft; the hat adds architecture. Strappy black or metallic heels lengthen the leg, and a small structured clutch with pearl or crystal drops is all the jewelry it wants. A boater has a flat crown and a stiff brim, so it reads sharper than a fedora; choose based on how polished the evening is. It suits cocktail hours and dinners outdoors.
6. Wide brim hat with swimsuit and sarong
At the beach I treat a big straw hat as sun protection first and style second, alongside sunscreen rather than instead of it. A one-piece swimsuit in terracotta, olive or navy with a coordinating sarong, an oversized floppy straw hat, flat thong sandals and a mesh or raffia tote. Big dark sunglasses finish it. Choose a hat with a tightly woven straw: loose weaves let spots of sun through, and a hat marked with a sun protection rating takes the guesswork out. For lunch, swap the wet swimsuit for a cotton cover-up dress and keep the hat.
7. Wide brim hat with jumpsuit and sandals
A wide-leg jumpsuit plus a hat takes about three minutes to put on and looks styled. Linen, Tencel or soft cotton in sand, olive or dusty blue, cinched with a fabric or leather tie belt. Flat sandals with minimal hardware, a straw fedora or boater and a raffia or woven leather crossbody. I'd choose a hat with a narrower brim here, around three inches, since the jumpsuit already has width at the leg. It's a strong travel-day outfit.
8. Wide brim hat with trench coat and ankle boots
For the crisp in-between weeks, a beige double-breasted trench over slim black trousers and a fine cashmere crewneck, with a black or charcoal felt fedora, is classic and practical. Block-heel leather ankle boots and a dark brown top-handle bag finish it. Keep the brim medium width; a very wide brim with a long coat tips into costume. Wool felt handles a light shower, but let it dry on its crown at room temperature, never on a radiator, or it will shrink and warp.
9. Wide brim wool hat with sweater and jeans
An oversized sweater and good jeans become an outfit the moment a felt hat goes on. Cable knit or smooth cashmere in cream, oatmeal or charcoal, front-tucked into dark high-rise straight or soft-flare jeans, with low stacked-heel suede ankle boots. A camel or charcoal felt fedora and a leather shoulder bag. The structured hat offsets the slouchy sweater so the whole thing still has shape. Chunky knits and big brims both add width, so if you're petite, choose a medium brim and a thinner knit.
10. Wide brim hat with leather jacket and skinny jeans
A black leather moto over a white crewneck tee with black high-waisted skinny jeans gives a hat a tougher setting. I'd choose a black felt fedora with a flat brim and a modest crown here, because a tall crown with a moto jacket can look like a costume. Lace-up combat boots or pointed booties, a silver chain, small hoops and a black leather crossbody. The hat softens the jacket's hardware just enough. Wear it to a concert or a night out.
11. Wide brim hat with midi skirt and blouse
A tucked blouse with a bias-cut midi skirt is soft and feminine, and a felt fedora gives it backbone. Burgundy, forest or caramel for the skirt; ivory or cream for the blouse. Pointed mules or ankle-strap heels and a structured mini bag keep the line sharp. Red lipstick is the only extra detail I'd add. For a bridal shower or afternoon tea, check the dress code; some daytime events welcome hats, and at others a big brim blocks people's view.
12. Wide brim hat with co-ord set
A matching set in linen, cotton twill or crepe, with a relaxed button-down and wide-leg trousers, can look like pyjamas on its own. A tonal straw or felt hat fixes that by putting a strong shape high on the body. I match the hat to the set or go one shade darker. Flat sandals or plain sneakers and layered gold chains finish it for travel, brunch or a gallery afternoon. Linen sets crease quickly, which looks fine; a creased hat brim doesn't, so carry it rather than stuffing it in a bag.
13. Wide brim hat with white cotton midi dress
A white cotton midi with eyelet, puff sleeves or a tiered hem is a blank canvas, and a straw hat with a navy or black grosgrain band adds the one dark line it needs. Flat tan sandals or espadrilles and a basket bag keep it warm and natural. That ribbon band also hides the join on many straw hats, so I'm careful not to pull on it. Wear it on vacation mornings, to a casual outdoor wedding, or for a sunny city day.
14. Wide brim hat with tailored vest and wide-leg pants
A tailored vest worn as a top with matching high-waisted wide-leg trousers is a strong vertical look. A structured felt or stiff straw fedora finishes the column at the top. Pointed loafers or low mules, a slim belt and a simple shoulder bag. I check that the vest doesn't gape at the armhole when you lift your arm, since that's where vests fail. It suits a warm office day or a networking dinner.
15. Wide brim hat with denim jacket and maxi dress
A denim jacket over a cotton or jersey maxi gives you structure over softness, and a straw hat ties the textures together. Throw the jacket over your shoulders or button it. Flat sandals or white sneakers, a canvas tote and simple hoops. I like a floppy straw brim with this one because the jacket already adds shape. It goes from a farmers market to a sunset dinner, and the jacket covers you when the breeze picks up.
16. Wide brim hat with crochet maxi dress
An ivory, cream or terracotta crochet maxi is open and textured, so I pair it with a solid straw hat that has a soft brim rather than another busy weave. A full slip underneath is not optional; open crochet shows everything in sunlight. Flat leather sandals or barely-there heels and a woven clutch or small structured bag. It's a resort dinner or rooftop drinks outfit. Crochet snags on rough straw, so carry the hat rather than tucking it under your arm.
17. Wide brim hat with shorts suit
A tailored shorts suit, blazer and high-waisted shorts in beige, olive or soft blue over a white camisole, is warm-weather power dressing. A felt fedora in a neutral that complements the suit sharpens it further. Strappy heels or low block mules and a compact structured bag. Felt in summer heat is warm, so I'd switch to a stiff straw fedora with the same shape on a hot day. It suits a creative office or a rooftop lunch.
18. Wide brim hat with maxi skirt and crop top
A drapey maxi skirt with a fitted ribbed crop top shows a sliver of skin, and a straw fedora or floppy hat gives the outfit a clean top line. Solid neutral or a fine stripe on the skirt, a coordinating crop, flat sandals or espadrilles and a natural leather or canvas crossbody. If you'd rather not show midriff, a longer fitted tee tucked into the high waist keeps the same shape. It suits festivals, vacation walks and casual evenings.
19. Wide brim black hat with all-black outfit
All black with a black wide brim hat is sleek, but it can flatten into one dark shape. The fix is texture: a ribbed knit, smooth leather boots, a soft-napped felt hat and a structured bag, so each piece catches light differently. Tuck the knit into black wide-leg trousers or straight jeans, add ankle boots or pointed flats and silver or gunmetal jewelry. Black felt shows dust and lint fast, so I keep a lint roller or soft brush by the door. Wear it to openings and dinners.
20. Wide brim hat with printed wide-leg pants
Bold printed wide-leg pants already have a lot to say, so the hat needs to stay neutral. Painterly floral, geometric or a subtle animal stripe on the pants, a solid fitted top in black, ivory or a color from the print, and a neutral felt fedora. Heeled sandals or pointed flats, a simple clutch and little else. If the hat and the print fight, the pants should win; swap the hat for a smaller brim. It's an outfit for a creative workplace or a dinner party.
21. Wide brim hat with button-down shirt and boyfriend jeans
A crisp white poplin shirt half-tucked into cuffed boyfriend jeans is classic weekend dressing, and a straw or felt fedora adds the finishing note. Roll the sleeves to the elbow, add flat loafers or low white sneakers, a leather belt and a simple crossbody. Tilting the brim slightly forward gives it a relaxed feel. I'd skip a very floppy brim with something this structured; a firm brim matches the collar. Wear it to market or coffee.
22. Wide brim hat with romper and espadrilles
A linen or cotton romper with a defined waist in olive, rust or chambray is one piece that does all the work. Espadrille wedges or flat canvas espadrilles and a soft floppy straw brim keep it beachy. A woven crossbody and oversized sunglasses finish it. Rompers are short, so a very wide brim can make petite frames look top-heavy; I'd go medium if you're under about five foot four. It suits a beach town afternoon.
23. Wide brim hat with long cardigan and straight jeans
Fall layering with a long cardigan gets soft quickly, and a felt fedora gives it vertical structure. A white or cream tee tucked into dark mid-rise straight jeans, a longline knit cardigan in oatmeal, charcoal or camel, and low-heeled suede ankle boots. Add a slouchy leather hobo. I match the hat to the cardigan so the long line runs from crown to hem. Suede boots on an apple-picking day need a protector spray first, since mud and wet grass mark them.
24. Wide brim hat with silk midi skirt and tee
High-low dressing is one of the most useful tricks I know, and a silk midi skirt with a plain tee shows why. A bias-cut skirt in emerald, rust or plum, a white or heather-gray crewneck tucked in, flat strappy sandals or pointed flats, and a neutral felt fedora. A structured top-handle bag adds polish. The tee keeps the skirt from feeling precious; the hat makes it memorable. Bias-cut skirts cling to the hip, so I'd wear seam-free underwear underneath. Wear it to a casual dinner or a date.
25. Wide brim hat with gingham dress
Gingham in navy, black or red with a square neck or puff sleeves is cheerful, and a straw hat with a ribbon band in the same color as the check makes it look intentional rather than costumey. Midi or mini, flat leather sandals or white sneakers, and a straw basket bag. I'd keep the hat's brim moderately wide here, since a huge brim with gingham can look like a picnic costume. Wear it to a park lunch or a market.
26. Wide brim hat with utility jacket and cargo pants
A field jacket and cargo pants are rugged on their own; a brown or olive felt fedora softens them and adds polish. A fitted tank or tee, olive or khaki cargo pants with a relaxed straight leg, and an unbuttoned utility jacket. Lug-sole boots or hiking-style sandals depending on the season, plus a canvas backpack or crossbody. It's my pick for an outdoor day or a road trip stop. Choose a crushable felt for trips; a stiff hat won't survive the back seat.
27. Wide brim hat with sweater dress and knee boots
A midi sweater dress in charcoal, camel or burgundy is a single warm piece for cold months. Knee boots with a low block heel, a wool felt fedora and a structured shoulder bag stretch the silhouette from crown to toe. Ribbed knits cling and cable knits add bulk, so I'd choose rib if you want length and cable if you want warmth. The boots should reach just below the dress hem, or the gap of leg breaks the line. Wear it for errands, a casual lunch or a bookshop afternoon.
28. Wide brim hat with turtleneck and wide-leg trousers
A fine black or charcoal turtleneck tucked into high-waisted wide trousers in cream, tan or olive makes a long column, and a black or camel felt fedora closes it at the top. Pointed flats or low mules, a slim belt and minimal gold. The slim top and full trouser balance each other, and the hat draws the eye upward. I always check that the turtleneck isn't too thick, since a bulky neck and a wide brim crowd the face. Wear it to galleries and lunch.
29. Wide brim felt hat with plaid blazer
A tailored plaid blazer in rust, camel and navy brings seasonal color, and a black or deep brown felt fedora adds a menswear edge. Underneath: dark skinny or straight jeans and a black crewneck or turtleneck. Black ankle boots, a sleek black shoulder bag and slim silver jewelry. Pick one color from the plaid for the hat band if it has one; it ties the two together. It's reliable fall street style for coffee or casual Fridays.
30. Wide brim hat with beach kaftan
A flowing kaftan in chiffon, cotton voile or silk with an open neck and wide sleeves, over a swimsuit or slip, is made for a big floppy straw hat. Flat embellished or thong sandals and a raffia or beaded clutch. The hat gives shade and drama; the kaftan gives ease. Kaftans in light fabric float in wind, so I'd add a hat with a cord or elastic, or you'll be chasing it along the sand. Wear it poolside or to a resort dinner.
Straw Versus Felt Through the Year
Material decides when a hat can be worn more than color does. I sort hats by what they can handle before I sort them by outfit.
- Toquilla straw (sold as Panama style): fine, light, breathable. Rolls or folds only if it's sold as packable.
- Raffia and seagrass: casual and forgiving, best for beach and vacation.
- Paper straw: cheap and light, but it softens and loses shape when it gets wet.
- Wool felt: warm, holds shape, handles light rain. Heavy for hot weather.
- Fur felt: smoother and more water resistant than wool, usually costs more.
Packing, Storing and Reshaping a Wide Brim
Most hats are ruined by handling, not wearing. I pick a hat up by the brim at the front and back, never by pinching the crown, because a pinched straw crown cracks along the crease. At home, a hat either hangs on a hook or rests upside down on its crown, so the brim isn't pressed flat.
For travel, wear the hat on the plane if you can. If it has to go in a suitcase, fill the crown with rolled socks and lay it on top of your clothes with the brim flat. A felt brim that has bent can usually be reshaped with steam from a kettle held a safe distance away, smoothed by hand and left to cool. Straw is less forgiving, so a crushed straw brim is more often a reason to buy a packable one next time.
One Felt, One Straw, and Most of These Outfits Are Covered
If you buy only two hats, make one a felt fedora in a neutral and the other a straw brim you can wear in heat. Between them, they cover nearly every outfit above. Keep the clothes simpler than you think, balance the brim against your shoulders and height, and let texture do what a second statement piece would do. Start with the outfit you'd wear anyway, a linen dress, a sweater and jeans, a blazer, and add the hat.
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