How to Wear a Hat... with Confidence

By Everyday Starlet
On Oct 31, 2015

This post appears in the Statement-Making Accessory: Hats campaign.

If my relationship with hats was a Facebook status it would be "It's Complicated". In my preteen years I had a bit of a love affair with hats (I blame Blossom, one of my favorite tv shows at the time starring Amy Farrah Fowler of The Big Bang Theory). Basically any black felt hat with a faux flower on it I wanted to be on my head.

For some reason, I fell out of love with hats in high school and college. However, in the early 2000s, when I was in my clubbing days, I had a fuzzy pink Kangol hat that was da bomb (and that saying was cool then as well). I had a few trucker hats at that time as well, but when they went out of style I broke up with hats again.

I had just accepted that I would live a hat free life... until recently. I've been seeing hats show up in the fashion world more often lately, but I just wasn't really to take the plunge. But on a recent trip to the new Primark in Boston I found a few inexpensive ones that caught my eye (the one I'm wearing, and this one from my Summer to Fall transition outfit). I think hats and I may be back together.

If you're thinking about getting together with hats, but you're afraid to take the plunge, here are some tips...

Size does matter. Not all hats are created equally, so try on a lot of them in different shapes and sizes to find the ones that go with your proportions.

It's all in the timing. Know when to wear a hat and when not to. Traditionally women can wear hats indoors and outdoors... men have stricter etiquette rules about wearing hats, although many ignore them (my normally very laid back father can go on rants about how inappropriate it is for men to wear a hat indoors). However, even for women, sometimes a hat is just not welcome.

Hats don't tend to lend themselves to formal occasions (although fashion rules are made to be broken). In addition, while it's not a rule, I'd recommend anytime your doing any public speaking, or you need people to see your face clearly, skip the hat.

Be complimentary. Your hat should be the cherry on top of your outfit sundae. You can go for a contrasting look, like a menswear hat with a feminine dress, but make sure your hat works with the rest of your outfit and doesn't compete with it. Treat a hat like any other accessory... because it is.

Don't try to hide. It's a misconception that hats are for hiding (bad hair days, a pimple, etc). Hats demand attention. I saw a quote once that said something like, "you'll always get more attention when you wear a hat." (I tried to find the exact quote, but it was a Google fail.) I have noticed that I attract a lot of attention when I wear a hat, which made me self conscious at first. However, now I figure why not have my Starlet moment... please, no pictures (big smile for the camera).

This look: Hat & Bag: Primark Boston Store//Neck Tie: a waist tie from a jumpsuit from Forever 21//Shirt: Charlotte Russe (no longer available, but any white shirt will work)//Jeans: Forever 21 (old)//Bracelet: BaubleBar Cabochon Stud Cuff//Shoes: Asos Harlequin Heeled Sandals (also seen in my off the shoulder top look)

Will you be wearing a hat this season?