Updated March 7, 2023

Wearing a fedora is an easy way to take your look to the next level. "But I don't look good in a hat!" you say. There's a hat for everyone. Just start trying them on until you're satisfied with the look and identify your unique style.
Hats and necklaces are some of my favorite accessories that complete a look! You may also be interested in these articles:
- Adding a scarf to your straw hat
- 6 ways to display my favorite hats
- Wearing a striking necklace: always in fashion
- A necklace inspired three looks
How to find and design the best hats
Today I'm going to share some of my favorite ways to style felt hats. And I offer some tips for finding fedoras (and other hats) that complement your face shape. I also add information aboutWoYou can wear your hats, as well as some guidelines forEto use them.
Wearing a felt hat: what clothes to match a felt hat
You will find that fedoras go perfectly with many different looks, including dresses, jeans, fun t-shirts, kimonos, leggings, etc. The list is endless. And I particularly love wearing mine with almost everything denim and/or lace.
Wearing a fedora with a dress
I paired my camel wool felt fedora, pictured below, with a favorite print dress, adding a camel moto jacket and matching camel boots. This look is also a great way to wear short sleeve dresses in fall and winter.

I have linked this exact camel hat for you below. And here is the same fedora insideGray brownis atnegro. You can also choose onelittle poplarin the same colors.
In the next two photos, I wore the same pink floral and leopard print dress in two different ways. You can get a completely different look just by changing boots, belts and hats. And when the temperature drops, you can pair the dress with a turtleneck or a long-sleeved T-shirt.


Tip: If you are interested in wearing more of her dresses throughout the year, you can read my postHow to wear a summer dress in winterand in this last postThe Printfresh clothing collection – My review. In the photo below, I pinned a long coat over a short-sleeved dress.

Wearing a fedora with leggings and boots
Wearing a fedora (or other hats) is a fun way to elevate any casual leggings and boots look. In one look, I put a scarf over a long top. And in the second look I combined a plaid flannel shirt with jeans leggings and boots. Anyway, the black fedora really completes the ensemble.


Wearing a fedora should be fun.
Try on different hats, in different shapes and sizes. Then try tilting them to the side or using them directly on your face. You can experiment with pulling them up to your brow line or pushing them further back on your head.
Why don't you stand in front of a mirror and play around with different hats worn from different angles until you find a few looks you're comfortable with? And definitely play around with different colors. I love the forest green fedora pictured below. Just see which look and color suits you.
Another fun look is wearing a cowgirl hat with jeans and a dress. This straw hat gives off all western vibes with its turquoise decor. This hat also features a "U Shape It" wire brim that allows you to shape the brim to best fit your face.

How to wear a fedora hat with short hair
Since I have short hair, I like to "fill in" the gaps where the bangs and slightly longer hair would fall. I manage this by wearing glasses or sunglasses or more defined eye makeup and longer or bigger earrings.

Another trick I use is using a scarf to draw attention from the hat to the scarf. And for that, I prefer slightly larger scarves that fall to the sides or back rather than a thin scarf that just covers the neck. (You can see an example of this tip in one of the leggings and boots photos above.)
When to wear a fedora hat
I've heard the theory that you wear a fedora from Labor Day (in September) to Memorial Day (in late May). At this point, swap out the felt hat for your straw hats. And your straw hat will get you to Labor Day and so on. However, I don't use this as a strict rule of thumb.
As with many other pieces of clothing (e.g. white pants), past fashion guidelines are a bit mixed. As for me, I agree that you can decide.
For example, I like to take hat color and temperature into account. For example, I may (or may not) choose to wear a black or other dark colored fedora during the warmer months here in the south.
And while I usually save my wool felt hats for fall and winter, I occasionally throw one on for a quick spring/summer outing, just for that special look. In the photos below I show a neutral fedora with spring and summer looks.



In short, you can wear the hat you like best and at the time of year that suits you best.
Where to wear your fedora hat (or other hats).
As I am targeting women with this post, I am told that they can wear their fedora anywhere, and certainly indoors as well. However, if your hat is blocking someone's view, remove it as a courtesy.
Also, it is not appropriate to wear the hat indoors at work. You can wear hats to religious services, weddings, indoor performances, etc. I also read that you don't have to take your fedora off during the national anthem.
If you are being introduced to someone, you can wear a hat. Think of this accessory as part of your outfit. For example, you wouldn't feel the need to take your scarf off when meeting someone or playing the national anthem.
Note: These guidelines apply to fedoras and other headwear known as fashion hats. They do not apply to a baseball cap, etc., as they will need to be removed much more often.
A tea party or brunch is a great place to wear your fedora. Consider hosting a tea party for friends and inviting them to wear their favorite hats. Or, if you have multiple hats, let your guests choose one to wear upon arrival. To havethis postfor tea suggestions andthis postto ideas for tea treats.
Wear a fedora (or other hat) that fits your face shape
There are many helpful guidelines for determining which hat looks best on specific face shapes. First, determine exactly what your face shape is. There are many articles and tutorials that explain in detail how to determine this. Once you know your face type, choose a hat (or hats) that you like to wear.
Fuller, rounder face
For example, a fuller/rounder face requires a more asymmetrical hat. Also remember that the softer, fuller lines of a round face require more angles. Therefore, tilting the hat so that the brim is angled is flattering. You can also try pushing the hat back on your head a little further, as this will add length.
Square face
On the other hand, if you have a square face, you should contrast the corners of your face with softer lines. Try wearing a floppy or wide-brimmed hat. These styles should help blur the angles of a square face.
Elongated and elongated face
If your face is long (oblong), avoid hats that replicate this shape and are considered tall and thin. It will only make your face look longer.
face oval
Ladies with oval faces can choose from almost any hat. To accentuate this face shape, try wearing the hat just above the brow line to frame the face. You can also lift the hat a little and position it just above the hairline, again to frame the face.
Consider bringing a friend (or friends) to get other opinions on what looks best on you. They could all try on hats together. That way, each of you can see how different types of hats look on different types of faces.
Again, there are plenty of articles and tutorials available to provide more suggestions for hats that will suit your face shape perfectly. Also, you can experiment with different earring shapes to find the style that works best for your face, not against it.
Ways to wear your felt fedora hat
This is your chance to get creative and add interesting elements to your hat. A basic idea is to add another ribbon. You can find them in almost any color to add interest to your fedora hat. Also, consider putting a feather in the angled band to give your hat a bohemian or cowboy look.
You can also choose to add a thin leather (or faux leather) strap that resembles a belt. Or you can simply add a buckle to the bracelet to give it the look of a belt.
For a vintage look, you can try adding a long folded scarf and tying it around the hat. In addition, you can also decorate it with pearls, rhinestones, turquoise or other jewelry. The Internet is a great source for more tips and tutorials on how to spruce up your fedora hat.
more hats
If you love wearing toquilla straw hats and are looking for ways to wear yours, I have this post.Adding a scarf to your straw hat.

And when you fall in love with hats and start collecting them, I have this post on6 ways to display my favorite hats.

buy felt hats
We participate in the Amazon Services LLC Affiliate Program, an affiliate advertising program that allows us to earn fees through links to Amazon.com and affiliate sites.As an Amazon affiliate, I earn a commission on qualifying purchases. However, this comes at no additional cost to you.
Fun Felt Hats Under $25
other fancy hats
These fancy felt hats are more expensive and come in over a dozen different colors. Pink is a personal favorite-very feminine!
Felt hats with UPF 50+ sun protection
These are some of my favorite sun protection hats. But you can find many others here.Coolibarand alsoAmazonas.
Thank you very much!
First, thank you for visiting and reading this post. I hope I've inspired you to find the perfect hats for your wardrobe and face shape.
Also, keep in mind that if you buy products through affiliate links, you may earn a commission for your purchases, but again, inNOadditional costs for you.Graciasfor supporting my work here by purchasing these links.
If you have any questions or comments, I'd love to hear from you. And hope to see you here again soon! In the meantime, you can follow me on Instagram.Hereor on PinterestHere.
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