Hat Tricks! | The Ins & Outs of Wearing a Hat

Hats are an accessory that can elevate a look and make you instantly look pulled together. But if you’ve never worn one before, wearing a hat can seem very overwhelming.

Black breton striped top, purple hair + black pork pie hat

While I don’t subscribe to any hard or fast rules for wearing one, here’s some general guidelines I follow as well as some answers to some questions you may be having about this headwear.

Feel free to come up with your own rules, makes things up along the way, and exercise your creative license to have fun!

How do you decide when to wear a hat?

  • Does it complete my “look”? Then I’ll wear a hat.
  • Do I want to follow the “rule of three” in my outfit and I need a third piece? Then I’ll wear a hat.
  • Does the weather call for one to protect my hair? Then I’ll wear a hat.
  • Am I having a terrible hair day? You bet I’m wearing a hat!

Patriotic outfit + straw boater hat

Where’s a good place to buy hats?

Because of my thrifty ways, I always start with second hand stores. But because that can be a drawn out process, I keep an eye on stores with hats that come in size options because I’ve got a small noggin. My go-to haunt is H&M.

Other places I’ve bought from that are great for sourcing hats but are mostly available in OSFM situations:

  • Abercrombie & Fitch
  • Amazon
  • ASOS
  • Forever21
  • Target
  • Urban Outfitters
  • Wal-Mart

Hats are somewhat seasonal depending on the style – especially wool or felt hats that only come out in the winter. If you’re on the hunt for something like that, buy them during their off season for the best deal. Any time between April and August should work.

Black pork pie hat + magenta hair

How can I wash a second hand hat?

Before I answer this, remember that even hats you purchase brand new from a retail store have a chance of being tried out by a slew of customers. Wear with caution!

  • If you’re talking about a knit/crochet hat, throw it in the wash. 
  • If you’ve got a structured deal, be much more careful because it would be devastating to ruin the shape of the hat. Start by simply using a Lysol wipe (or equivalent) to brush off any surface germs. If you’re still weary of putting it on your head, look into a DIY hand washing method (like this one) or finding a professional hat cleaner in your area. They’re pricey but they know what they’re doing!

How do I keep a hat on my head?

  • Knit/crochet hat: Using bobby pins work in a jiffy.
  • Baseball caps: These are adjustable and, if your hair allows, can be held up with a bun or ponytail. 
  • Wool/felt hats: My non-committal DIY trick is lining my hats with stacked up sticky-back foam to form a tight grip. This is usually used for weatherproofing windows but is surprisingly useful for resizing hats!
  • Wool/felt hats: You can get even more drastic when it comes to resizing a structured hat and use a method demonstrated on this page for shrinking a hat or this thread for expanding a hat. I’ve never personally done either so proceed at your own risk.

Other tips: Teasing or curling your hair could be just the trick you need!

Curly brown hair and a white slouchy knit hat. Bright outfit with orange lipstick.

Should I take my hat off when I’m indoors?

  • If the hat is part of your look and adds to your outfit, keep it on.
  • If a hat is merely a shield from the weather, take it off.
  • If the hat is a cover-up for a bad hair day, definitely keep it on!

This rule gets muddy when casual beanies are in play so you’ll just have to use your best judgment. I don’t personally have any qualms about wearing a hat indoors, I think it comes down to being a personal preference. Do what makes you feel comfortable!

How can I customize the look of my hat?

  • Pins, brooches, and scarves are great tools to transform the look of an ordinary hat.
  • Strategically pinning the brim of a hat can change the entire shape and give you a unique style.
  • Why not construct one out of a headscarf? It’s a simple way to cover your hair without the commitment of buying a hat you may only wear once.
  • A more permanent way to change the way you look at your entire hat collection is to color your hair. You’d be amazed at how different a green hat looks on brown hair vs. purple hair. It’s a big commitment but it’s sure to liven things up!

Changing the look of a slouchy knit hat with a vintage brooch.

Wearing a headscarf in place of a hat.

Cotton candy pink hair and a vintage teal beret.


If you don’t already wear hats then what are you waiting for? There’s a world of variety out there and and styles to suit every wearer. I never thought I was a hat person before I tried my first bowler hat. Keep looking until you find the right one!

If you’ve got any other questions about hats, leave ’em below. I may do a follow-up post in the future if there’s enough interest!

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  • You’re so stinkin’ adorable. I love hats – I used to wear them ALL THE TIME when I had short short hair. I don’t wear them as often anymore (hardly ever!) but there are days where I am tempted. It’s tough though – with my curly hair, once a hat is on my head, I am COMMITTED until bed time. haha

    saralilyphoto.blogspot.com

    • Hahaha oh my gosh, the hat head is so much crazier with curly hair! Thanks, Sara!

  • nmettille

    Wearing stuff on my head is my favorite. But, I’ve never tried a straw hat…I could wear straw on my head. I think that’s going to happen this summer.

    http://www.theclassyjunk.blogspot.com

    • You’ve gotta try it at least once in your life!

  • Yep, the only things I’ve worn in my hair/on my head include beanie hats, scarves, and the occasional flower pins. I asked for one of your hats recently though, so with these tips I’m REALLY praying I can pull it off! 😀

    • Hey, it’s takes a certain person to pull of headbands and you are doing it right!! And I’m crossing my fingers for you. One of these days you’ll become a hat person. 😉

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