Types of Hats & How to Style Them Right

girl with hat

Discover how to pair hats the right way—and it’s a total game-changer! Here’s a quick guide to 5 popular hat types and how to wear them effortlessly.

1. Beret
This hat oozes femininity and romance. Pair it with flowy skirts or dresses. Avoid edgy pieces like moto jackets—they clash with the beret’s soft charm. Opt instead for cozy knits and relaxed coats.

2. Brim Hat
Elegant and dramatic, brim hats need balance. Because of their volume, match them with longer-length coats or midi skirts. Shorter jackets and casual outfits may feel out of sync.

3. Newsboy Cap
Modern and edgy, newsboy hats work best with structured pieces—think blazers or belted coats. Materials matter too: faux leather versions pair well with similarly edgy textures.

4. Beanie
The ultimate casual winter hat! Beanies add warmth and a youthful touch. They go great with relaxed fits like sweaters, jeans, and playful skirts. Just avoid overly structured coats—they can throw off the beanie’s laid-back vibe.

5. Bucket Hat
Usually a summer staple, bucket hats also work in winter if made with materials like faux leather. Since they’re casual and unstructured, pair them with easygoing knits and relaxed outfits.

Style Tip: Match the “vibe” of the hat with your outfit’s shape, structure, and texture. And don’t forget your face shape—it plays a big role in how hats look on you!

Choosing the right hat can elevate your look instantly. It’s all about harmony between your hat, outfit, and personality.

Nail Hat Fit for Your Face Shape (The Missing Piece)

You could pick the perfect hat-outfit combo, but it won’t shine if it doesn’t flatter your face shape. Let’s break down how to tweak each hat type for your features:

  • Round faces: Aim to add length. For berets, tilt them slightly to one side (not straight on) to create angles. Brim hats work best with a medium-width brim—too wide can overwhelm, too narrow won’t balance. Skip tight beanies; go for slouchy styles to avoid making your face look rounder.
  • Square faces: Soften sharp edges. Berets and bucket hats (with a slight slouch) are ideal—their curved lines contrast with strong jawlines. Avoid rigid newsboy caps or straight-brim hats; opt for ones with a slight bend in the brim.
  • Long faces: Add width to balance. Brim hats with a wider brim (think 3–4 inches) help shorten the face. Newsboy caps with a structured crown also add fullness. Skip tall, narrow beanies—they’ll stretch your face further.
  • Heart-shaped faces: Focus on the forehead and chin. Berets worn forward (not tilted back) cover a wider forehead gently. Bucket hats with a shallow crown work too—they don’t pull attention to a pointed chin. Brim hats? Go for a brim that dips slightly at the front to soften the hairline.

Seasonal Tweaks: Make Hats Work Year-Round

Most hats aren’t “one-season only”—a few material swaps or outfit adjustments let you wear them 12 months a year:

  • Berets: Summer calls for lightweight linen-cotton berets in pastels or prints—pair with a sundress and espadrilles. Winter swaps to wool or cashmere berets in deep tones (burgundy, charcoal)—layer with a wool coat and scarf.
  • Brim hats: Summer = straw or rattan brim hats (great with linen pants and a tank top). Winter = felt or wool brim hats (pair with a long wool coat and knee-high boots). Just make sure winter brims are lined—unlined felt can feel scratchy in cold weather.
  • Newsboy caps: Summer = cotton or canvas caps (match with a linen blazer and chinos). Winter = faux leather or wool caps (pair with a leather jacket or puffer coat). Add a small pom-pom to winter versions for extra coziness.
  • Beanies: Summer = thin cotton or bamboo beanies (for cool evenings at the beach—wear with a hoodie and shorts). Winter = thick knit or fleece beanies (layer over a turtleneck and parka). Look for beanies with a fleece lining if you hate scratchy wool.
  • Bucket hats: Summer = lightweight nylon or cotton (print styles work with a t-shirt and shorts). Winter = faux fur or quilted bucket hats (pair with a chunky sweater and jeans). Avoid thin summer fabrics in cold weather—they’ll do nothing for warmth!

Accessory Hacks to Tie Hats to Your Outfit

Hats don’t exist in a vacuum—small accessories can make them feel like a part of your look, not an afterthought:

  • Color Echo colors: If your beret is cream, add a cream scarf or a bag with cream accents. A black newsboy cap pairs perfectly with black ankle boots or a black belt. This “color echo” pulls everything together without effort.
  • Texture match: Faux leather bucket hats? Pair with a faux leather jacket or gloves. Wool beanies? Add a wool scarf or a coat in the same texture. Mixing textures (like a cotton beret with a silk blouse) works too—just keep one texture dominant.
  • Hair matters: For berets and newsboy caps, pull a few face-framing strands loose—this softens the look and keeps hair from poking out awkwardly. For brim hats, wear hair down (wavy or straight) or in a low bun—high ponytails can make the hat sit lopsided.
  • Glasses & hats: Round glasses pair great with structured hats (newsboy caps, brim hats) to balance shapes. Square glasses work with soft hats (berets, bucket hats). Just make sure your hat doesn’t push your glasses up—adjust the hat’s position until it feels comfy.

Occasion-Ready: Wear Hats to Any Event

Hats aren’t just for weekends—they can elevate even formal or semi-formal looks. Here’s how to style each hat for different moments:

  • Casual outings (brunch, errands): Slouchy beanie + oversized sweater + jeans, or cotton bucket hat + t-shirt + denim shorts. Keep it relaxed—no need for perfect symmetry.
  • Work/commute: Newsboy cap (wool or cotton) + blazer + tailored trousers, or beret (neutral tone) + turtleneck + midi skirt. Stick to muted colors (black, navy, cream) to keep it professional.
  • Date nights: Wool beret (deep red or black) + silk camisole + midi dress + ankle boots, or small brim hat (felt) + long coat + heeled loafers. Add a little sparkle (like small earrings) to keep it romantic.
  • Outdoor events (concerts, picnics): Straw brim hat + linen dress + sandals (summer), or quilted bucket hat + chunky sweater + ankle boots (winter). Prioritize comfort—you’ll be wearing the hat for hours!

Final Tip: Confidence Beats “Perfection”

You might overthink if a hat “looks right”—but the best hat looks are the ones you wear with confidence. If you love a beret but worry it’s “too feminine,” wear it with a leather jacket (yes, we broke the earlier rule—but rules are flexible!). If a bucket hat feels too casual for work, pair it with a blazer to dress it up.

Hats are supposed to be fun—they’re a way to add personality to even the simplest outfit. Don’t be afraid to experiment: try tilting a beanie differently, or swapping a summer brim hat for a winter one. Over time, you’ll find what feels like you.

At the end of the day, a hat is more than an accessory—it’s a way to show off your style without saying a word. And when you get that combo right? Heads will turn—for all the right reasons.

Uncover further inspiration in our blog.

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Picture of Aveline Lux

Aveline Lux

Aveline Lux is a visionary writer and digital storyteller, using her blog on CitiWell Shop as a platform to explore the intersection of creativity, commerce, and culture.

Traveling extensively across continents, Aveline draws inspiration from different cultures and global trends, infusing her articles with unique perspectives and practical insights.

Aveline enjoys photography, hiking through nature trails, and curating playlists that fuel her creative process.

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