The Do’s and Don’ts of Styling Hats with Your Outfits

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Hi, I'm Chelsey

Remember not too long ago when I mentioned hats as a beauty and style essential? Well, I’m very much aware that hats can be scary territory. While it may seem contradictory because my face is essentially the face of the Venti Fashion brand, I don’t like being the center of attention. If you’re the same way, hats can feel a bit out of your comfort zone. Depending on the size and style of the hat, it pretty much demands attention. You’re making a statement, after all!

dos and donts of styling womens hats

Outfit Details: Top: Zara (similar) | Jeans: Zara | Hat: Target | Shoes: Sam Edelman | Bag: Street Level

Don’t let the fear of people staring deter you from throwing on a hat! There are a few reasons why you need one in your seasonal rotation:

  1. Hats are the perfect topper to finish off any outfit.
  2. A hat that complements your outfit helps you look put together.
  3. Hats can salvage your look during those bad hair days.

Are you eager to give hats a try? Below are some of the do’s and don’ts that will help you style hats with your outfits. Remember, confidence is always key! There was once a time where I felt extremely out of place with a red lip, but I have since grown to love it! The easiest way to try out new trends is to adopt the Nike lifestyle and just do it. Use the tips below to help navigate your styling concerns and challenge yourself to wear a hat with your next outfit!

How to Style a Womens Hat-4

The Do’s and Don’ts of Styling Hats with Your Outfits

  • DO: Wear a hat that matches your outfit. 
  • DON’T: Throw on the first hat you see. Similar to grabbing the first jacket you see on your way out the door, randomly grabbing a hat turns the outfit from intentional to one of convenience. If you want to style a hat, the first step is actively picking one that completes your look.
  • DO: Make sure the hat and the outfit are sending the same message. A straw hat with a winter outfit or a fuzzy beanie with a summer outfit looks a bit confusing. When you want to add a hat, think about what season you’re in as well as what your outfit is saying. Shorts and dresses look great with straw hats, berets pair nicely with minimalist outfits, caps mix with the vibe of airport outfits, and beanies go well with scarves.
  • DON’T: Pair a hat with a dressy outfit. There are a few small exceptions but for the most part, only Janelle Monae has the style resume to execute the balance of a hat with a formal outfit.

How to Style a Womens Hat-4

  • DO: Find a hat that appropriately fits your head. Think of hats like the classic children’s tale with the porridge and the three bears. The goal is to find a hat that fits just right so you aren’t adjusting it throughout the day. Fidgeting with your clothes comes across as feeling insecure, and that’s the opposite of what you want your style to say.
  • DON’T: Wear a hat that’s too tight or too big. If you wear a hat that’s too tight, you’re likely to either get a headache by the end of the day or end up with an indent across your forehead where the hat rests. If you pick a hat that’s too big, it disrupts your natural proportions and looks unbalanced.

dos and donts of styling womens hats

  • DO: Style your hair to complement the hat. You wouldn’t wear a top knot with a hat (obviously), but the same goes for styles with hair clips or bobby pins. Realistically, bobby pins aren’t bulky so they can be worn underneath a hat with ease. That being said, it’s a good idea to skip them so the pins don’t rub against the hat and cause discomfort. If you want to take your hat off at any point of the day, it’s much easier to fluff out the hat hair when you don’t have any pins to style.
  • DON’T: Completely skip the hair routine. Yes, it will take less time to style your hair, but you do still want to ensure all the tangles are gone or your hair is braided to the side. The reason for this is you want the look to be intentional rather than unfinished.
  • DO: Wear the hat with confidence and a smile. Pretty self-explanatory, right? Confidence can make or break an outfit!
  • DON’T: Hide behind the hat. It’s an accessory, not a cloak. Not to mention, hiding behind a hat makes you appear uncomfortable and uneasy, which makes it impossible to do the above tip.

dos and donts of styling womens hats

When in doubt, get a second opinion! Ultimately what you wear and how you style it is up to you, but it’s nice to get another person’s perspective when you’re feeling unsure. Below are a few hats to help kick off your collection:

Which hat is your go-style for each season?

Need more inspiration? Follow on Instagram to see my IGTV, or watch the extended YouTube version below:

FTC: This post contains affiliate links, meaning, a commission is received when purchases are made. Please show your support by shopping the links! 

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