Hats for a First Date

A Safe Date Look

A quiet, yet sure date look

If you are preparing for your first date with a certain someone and would like to make a huge impression yet also be comfortable and confident while doing so, wear a hat that you are accustomed to and know that you look good in.

Trudy Feighery might suggest this hat she made.

This hat by Trudy Feighery may be overly bold on your first date; save it for the second date.


The first date may not be the time to try that saucy hat that you’ve had your eye on for quite sometime but aren’t quite sure about. You don’t want to have to worry about keeping a new hat on your head or whether it looks good on you. Your attention should be on your date. After all, you only have one first date with a person.

Of course, your choice of hat depends on the time of the year, the time of day, where you are going and what you will be doing. If you are a man going to the movies, you don’t want to bring a tall top hat and cane, even if it’s a classic movie! That could upset anyone sitting behind you and mark you as weird at the same time.

Sexy Hat by Lisa Habig - don't take it to the beach!

Sexy Hat by Lisa Habig - don't take it to the beach!

Avant garde and eccentric? Rein it in on the first date. A feather hat in the middle of a summer day at the beach might be a stretch — a bit out of place, and make your newfound friend question his decision to ask you out. Save the quirkiness for a little later in the relationship. Then again, if you were wearing an outrageous feathered fascinator, and weren’t on your way to a royal wedding the first time he set eyes on you, and he still asked you out, then go for it. He already knows that you are unconventional and likes it.

The slouchy beret, which can be crocheted or an oversized cable knitted beanie hat – such as David Beckham or Ashley Simpson frequently wear – is a


David Beckham / Ashley Simpson Slouch Hats

Project Hip, Famous, Young & Rich: David Beckham / Ashley Simpson Slouch Hats


really good look for a first date. It’s not over-the-top, but it is definitely eye-catching. If the weather is cool, it will keep you warm. The way you wear it, how much it slouches, the jaunty placement on your head, tells a lot about you.

The Style of the Roaring 20's on Angelina Jolie

The Style of the Roaring 20's on Angelina Jolie

If you are into retro and enjoy channeling styles from bygone eras, select a cloche, which is reminiscent of the 1920s and the saucy flappers of that time. The 1920s was the era when women first bobbed their hair and wore short skirts revealing some skin (scandalous!). The flappers were skillfully flirtatious!

A cloche can be worn with casual clothes, jeans and a jacket and some kick-ass boots, or with a more upscale ensemble. Once you don a cloche you are destined to flirt, and you should do so by all means.

Is She Flirting with Me? Hat by Harriet Rosebud

Is She Flirting with Me in that big hat too? Hat by Harriet Rosebud


Hats are great flirtation devices.

Hats have been an integral element of fashion since the beginning of time. Hats provide protection from the elements. They keep you warm in the winter and shield your face from the sun in the warm weather months. Aside from their functional capacity, hats are a perceptible fashion accessory. They’re hard to miss. Even the smallest of hats is going to be noticed. Have you ever heard the expression, “If you want to get ahead and get noticed, then get a hat”?

Your face gets noticed in a hat

Your face gets noticed in a hat

A hat draws attention to your face. The right hat — and you may have to try on several “frogs” before you find your “prince”– is unabashedly flattering because it emphasizes your face. Hats complete an ensemble. A spectacular hat speaks for itself.

Hats are also a great camouflage if you are having a bad hair day. No one has to know what lies underneath. Of course, if it’s a first date you really might want to wash and style your hair before venturing out, hat or no hat.

Guest post by Cindi Pierce.





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