Hats & Heels

Name a better duo! From our guest contributor: Hana Freeman

Hats & Heels

When it comes to hats and heels, in my opinion, there have never been two items more similar. These are your bookend pieces to your look, and although their physical shapes and their purposes are strikingly different, the details that make these pieces work as functional accessories in your life are the same. 

I find the two pieces so empowering to combine because here you are taking something that is so typically masculine and pairing it with something that is so typically feminine. And blending those two things together kind of makes me feel like a boss, and like I am in the driver’s seat of my look - it deconstructs what is expected, makes it fun and sexy and it can be done in a variety of ways. Below are some of my favorite ways to wear this combo. Again, your fashion works for you, and not the other way around, so don’t forget that YOU decide what works and what doesn’t. Here’s what works for me:

 BASIC Hat and Heels: My style philosophy at this point in my life is mostly about ease. And though it’s typically against popular belief, I do strongly believe fashion can be easy and comfortable. Which is why I always love to start with a denim and white t-shirt or tank top combo. As you probably read in the previous blog post “ Simple Styling”, this classic combo has stood the test of time because it is easy and accessible to all of us. Where hats and heels come in, is they really help elevate this look and expand it’s ability to go from day to night, or from one location to another. I love to pair my taupe Colonel Pierce with this combo because even though this hat is such a statement, in its neutral tone mixed with the neutrality of this outfit (plus some great and easy mules) I know I’m going to be happy lady for the entirety of my day, event, what have you. I know in this look I won’t be worrying about what Im wearing because it’s a guaranteed knockout. 

BREEZY Hat and Heels: Next up is an easy going ensemble that I think combines hat and heels in a way that communicates a little more elegance. For summer material is a very important detail to consider when I am choosing an outfit. I love linen, who doesn’t? Its breezy, its light and often comes in an array of beautiful desert tones…it just gorgeous! Not to mention keeps you cool. So I thought it was only natural to pair my linen dress with a Welfleet - a similarly breezy hat- AND, wait for it…a low blocked heel! Yes a lower heel is still a heel! Ladies we don’t have to be sky high to look fashionable or beautiful! Let your hat be what takes you to new heights not your heels! We just came out of almost two years of wearing sweatpants exclusively, its ok to pace yourself and this is my version of that pace. If I am going to tap into a look that is more feminine I like to live here. The elements of this outfit give an illusion of effort but no one really knows how simple and effortless it really is.

COCKTAIL Hat and Heels: Remember cocktail hour and going out? Do you also remember how uncomfortable that look has always been?? Tight dress, high heels… no thanks! As per my style, in addition to ease and comfort, I like a little deconstruction when it comes to the staples for women. So in light of that I find that a LBD (little black dress) just so happens to pair perfectly with a cattleman pinch fedora, the Giddy Up is featured here, and some heeled booties. This hat, even being as specific as it is, can truly transform into a neutral depending on how you style it. Additionally, depending on the details of your ensemble, this hat can actually translate to a look that, in my opinion, is pretty rock n roll! I at least feel like a rockstar in this combo. Also I know because of these heels (yes booties are still heels) I am going to continue feeling that way all night because booties give the height and sexiness of a stiletto but comfort that will let you be out all night or comfortably home before ten. I cannot repeat it enough it is all about mixing the comfort with the cool.

BOLD Hat and Heels: Last but certainly not least, I thought it might be fun to go all the way with something bold, and this suit is certainly that! Unlike the previous looks, I wanted to pair this relatively non-conforming piece with a hat and heels which in my opinion help aid to give it shape. This ensemble for me is all about balancing the tone. The suit in this case gets to be my masculine piece, where I get to soften that look is in the heels and the hat. Now I decided to pair my suit with our Makalu which is an open crown. This particular blocking of a hat does tend to lean more feminine to me and of course in this bone color it offers the freedom to translate it however I like and pair it with ultimately ANYTHING! Neutrals paired with neutrals is awesome and I do it often but neutrals paired with bold patterns and shapes, don’t mind if I do!

Bottom line of all of these looks is that you can and should play when it comes to your fashion. Remember these are mere suggestions from one person so I encourage you to trust your instincts! But don’t forget whether you are going bold or staying neutral I promise you there’s no wrong choices AND… there’s a hat and heels combo for it!

Big shout out to Hana, of our Virtual Styling Team, for writing this piece! Remember, our virtual styling appointments are free to book here

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