Styling Outfits

The Best Ways to Accessorize Your Outfit with Hats

A guide to hat shapes, how they relate to face shape and occasion, and which hats suit each season, from sun hats and caps to beanies and fedoras.

On this page
  1. Hats as both practical and decorative
  2. Common hat shapes
  3. Matching hats to face shapes
  4. Getting the fit right
  5. Hats by season
  6. Pairing hats with outfits
  7. Hair, glasses and hats
  8. Care and storage

Hats as both practical and decorative

Hats have long been functional: they shade the face, keep the head warm and protect against rain. Today they are also a style choice. A hat sits at the top of an outfit, close to the face, so it gets noticed quickly. That makes it one of the stronger accessories, and it can carry an outfit by itself. Many people feel awkward in hats at first. Most of the time, that comes from not having found the right shape and size, not from a lack of ability to wear them.

Common hat shapes

  • Baseball and other caps. A rounded crown with a stiff or soft bill. Casual and sporty, and they suit jeans, tees and sneakers.
  • Beanies and knit hats. Soft knitted caps for cold weather. They can sit snug on the head or slouch behind it.
  • Bucket hats. A soft hat with a short, sloping brim, casual and easy to pack.
  • Fedoras and trilbies. Structured felt hats with a pinched crown, typically with a band. The fedora has a wider brim and the trilby a shorter one.
  • Wide-brim hats. Big, floppy or stiff brims that shade the face and shoulders, often in straw or felt.
  • Straw hats. Boaters, panamas and sun hats woven from straw or similar fibers, mostly for warm weather.
  • Berets. Soft, flat, round caps usually made of wool, worn at an angle.
  • Newsboy or flat caps. A rounded, soft crown with a small brim in front.
  • Cloche hats. Close-fitting, bell-shaped hats with a small brim, linked to styles of the 1920s.

Matching hats to face shapes

As with sunglasses, the common guideline is contrast. It is only a starting point.

  • Round faces are often paired with hats that have height or angular lines, such as a fedora with a higher crown.
  • Square faces may be softened by rounded crowns and curved brims.
  • Long faces often look balanced in hats with a wider brim or a lower crown, rather than a very tall one.
  • Oval faces are generally versatile and can wear many shapes.
  • Heart-shaped faces might suit medium brims, which balance a narrower chin.

Proportion between the hat and your overall frame matters too. A very wide brim can overwhelm a petite frame, and a very small hat can look lost on a tall one. Try different sizes and look at the whole outfit in a full-length mirror.

Getting the fit right

A hat should sit comfortably without pressing on the forehead or sliding when you move your head. Sizes are usually based on head circumference, measured around the widest part of your head above the eyebrows and ears. Brands vary, so check each size chart, and look for inner bands or adjusters that can be tightened. A hat that is too small may cause headaches, and one that is too large will blow away or fall over the eyes. Use the same care as with body measurements when measuring.

How you wear it matters. Position the hat level and slightly forward, and decide how much of your hairline to show. Pulling a hat low creates a mysterious feel, while pushing it back is more relaxed.

Hats by season

Spring: Light brimmed hats, bucket hats and caps handle changeable weather. A felt fedora in a light color suits cooler spring days.

Summer: Straw hats, wide brims and breathable caps shade the face and keep you cooler. Natural fibers tend to be more breathable, and lighter colors reflect heat. The note on climate fabrics gives more on warm-weather materials.

Fall: Felt hats, berets, newsboy caps and wool fedoras suit milder cold. They go well with scarves and light coats, including a trench coat.

Winter: Beanies, knit caps, hats with ear coverage and fur-style or lined hats are practical. Wool garments such as knitted hats provide warmth, and a lining can make them more comfortable on sensitive skin.

Pairing hats with outfits

The easiest hats are the ones that echo the formality of the outfit.

  • Casual outfits take caps, bucket hats, beanies and straw hats well.
  • Smart casual outfits can include a felt fedora, a flat cap or a beret with a coat and tailored trousers.
  • Formal events have their own traditions, such as hats or fascinators at some weddings or races, so check the invitation and local custom.
  • Sporty outfits suit caps and visors designed for performance.

Think about color too. A hat in a neutral shade, such as black, camel or gray, goes with most wardrobes. A hat in a bold color works best when the rest of the outfit is simple. If a hat is the focal point, consider keeping other accessories restrained, as the general accessorizing guide suggests with its advice on choosing one or two standouts.

Hair, glasses and hats

Hair interacts with a hat. Long hair can be worn loose, braided or tucked, and shorter hair may need a smoother finish if you want to avoid hat hair. Glasses work with most hats, though very wide frames and wide brims together can look heavy. See the notes on sunglasses for tips on frames that pair well.

Care and storage

Store hats so that they keep their shape: stuffed with tissue, on a stand, or upside-down on the crown rather than the brim. Keep felt away from moisture and brush it gently, and avoid crushing straw. Wash knitted hats following their labels, and check seasonal storage tips for hats you put away.

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