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How to wear a hat with medium hair?

Published in Hat Hair Styling 5 mins read

To wear a hat effectively with medium hair, the key is to consider both the hat style and your desired look, ranging from sleek and tucked away to loose and flowing. You can achieve various stylish outcomes by styling your hair either fully under the hat, pulled through an opening, or left to frame your face.

Styling Your Medium Hair for Any Hat

Medium-length hair offers fantastic versatility when it comes to hats. The best approach often depends on the type of hat and the overall aesthetic you're aiming for.

1. Sleek and Tucked Away

For a clean, polished look, especially with fitted hats like beanies, fedoras, or even baseball caps, a sleek, tucked-away style works wonders.

  • Process:
    1. Brush your hair back smoothly away from your face.
    2. If you have layers, you might use a light hairspray or styling cream to keep them in place.
    3. Gently place the hat on your head, ensuring all your hair is tucked underneath.
    4. Pro Tip: For a truly sleek appearance under a cap or beanie, slick your hair back and then put on your hat. This prevents bumps and ensures a smooth silhouette.
  • Best for: Beanies, berets, fedoras, cloches, newsboy caps.

2. High Ponytails and Top Knots

These styles are perfect for keeping your hair completely off your neck and are particularly well-suited for hats with an opening at the back.

  • Process for Ponytail:
    1. Gather your hair into a high ponytail, positioned where the opening of your hat would sit.
    2. Secure with a hair tie.
    3. Put on your cap, and then pull your ponytail through the hole above the strap to keep it out of the way and create a neat, sporty look.
    4. Adjust the hat for comfort.
  • Process for Top Knot/Bun:
    1. Gather your hair into a high bun or top knot, ensuring it's positioned to align with the hat's opening.
    2. Secure tightly.
    3. Place your cap on, allowing the bun to sit comfortably through the opening.
    4. Alternative: Even without an opening, you can try putting your hair in a top knot (or a low bun) before wearing your cap or a looser hat like a beret, tucking the bun flat against your head or underneath the hat.
  • Best for: Baseball caps, trucker hats.

3. Loose and Flowing Styles

For a more relaxed, bohemian, or elegant look, letting your medium hair flow naturally around your shoulders or over your back can be incredibly chic.

  • Process:
    1. Wear your hair down, either straight, wavy, or curly.
    2. Place the hat on your head, allowing some strands to fall naturally around your face. You can tuck side pieces behind your ears or leave them out for softness.
    3. Adjust the hat to sit comfortably, not too far back or too far forward.
  • Best for: Wide-brimmed hats, fedoras, sun hats, berets, bucket hats.

4. Braids and Half-Up Styles

Braids offer an excellent way to manage medium hair while adding texture and interest, whether tucked or left visible.

  • Braids:
    • Side Braid: Create a loose side braid and let it drape over your shoulder. This works well with various hats, including beanies and fedoras.
    • Two Braids: Part your hair down the middle and create two pigtail braids. You can either tuck them under your hat or let them hang freely, which is particularly charming with beanies or bucket hats.
    • Low Braid: A low, loose braid can be tucked under the back of almost any hat for a tidy but soft look.
  • Half-Up, Half-Down:
    • Pull the top section of your hair back into a small ponytail or half-bun. This can be tucked under the hat or left visible if the hat allows. The rest of your hair remains down. This adds volume at the crown without overwhelming the hat.
  • Best for: Beanies, fedoras, bucket hats, berets.

Hat-Specific Styling Tips

Different hats complement different hair strategies.

Baseball Caps & Trucker Hats

These are inherently sporty.

  • Classic: A high ponytail pulled through the back opening is a go-to.
  • Modern: A high messy bun (top knot) peeking through the opening gives a casual, trendy vibe.
  • Sleek: For a more understated look, slick your hair back into a low ponytail or tuck it entirely under the cap.

Beanies

Beanies are excellent for warmth and style.

  • Loose & Down: Let your hair fall naturally around your shoulders.
  • Side Part: Create a deep side part to add volume and asymmetry.
  • Tucked: For a truly snug fit, tuck all your hair completely under the beanie.

Fedoras & Wide-Brimmed Hats

These hats often add sophistication.

  • Effortless Waves: Let your medium hair flow in loose waves for a romantic, chic feel.
  • Low Ponytail/Braid: A low, loose ponytail or a side braid can peek out from under the back of the hat.
  • Tucked Behind Ears: Simply tucking the front sections behind your ears can frame your face beautifully.

Berets

Berets offer a touch of Parisian chic.

  • Side Swept: Sweep your hair to one side, letting it fall over your shoulder.
  • Loose: Wear your hair down and let the beret sit gently on your head.
  • Sleek: A neat low bun or slick your hair back and tuck it under for a very elegant profile.

Combating "Hat Hair"

To minimize flat spots or static after removing your hat:

  • Dry Shampoo: A quick spritz at the roots before or after wearing your hat can refresh volume.
  • Volumizing Spray: Apply lightly to roots before putting on your hat, or use to reactivate volume afterward.
  • Headband Underneath: A silk or satin headband worn under your hat can reduce friction and static.
  • Finger Styling: After removing your hat, use your fingers to gently tousle your roots and redistribute volume.

By experimenting with these techniques, you can confidently integrate hats into your style, making the most of your medium-length hair.