How To Dress Up With Hats | Vintage Women

Headwear time again! With hats (and other types of headwear) being overlooked by most women today, lots of ladies that do find them appealing, require knowledge to know how to dress up with hats. For this reason, we compiled a series of outfits, involving some of the most popular types of headwear.

As with other similar posts, pictures of numerous outfits are presented to help you visualize these, plus even more, suggestions are given by us right next to them.

Outfits from different eras are presented, so no matter what type of clothing you are into, we got you covered 🙂

Stay tuned for more outfits with hats suggestions coming soon!

Outfits around Beret Hats

Berets are one of the few hats that you can still frequently spot on a normal day out, especially in European countries. These are one of the most versatile hats since they can have a place in traditional and modern outfits and combination with almost any type of casual apparel.

As an example of what to expect in a traditional look, take a look at the following suggestion

The first thing to notice is that berets are not restricted to cold weather apparel. Short and long-sleeved tops can work with them as well as numerous types of skirts and short dresses.

As you can see, they are also very vintage friendly as they go really well with patterns like stripes and polka dots, which were an essential part of fashion during the mid-XX century.

If you go for a printed top, matching one of the colours to the one on your beret will be a good start, this will make the hat merge more seamlessly with the rest of the outfit, however, if you wish the hat to stand out above all (not so common on traditional outfits) you should choose a totally different colour for it.

The shape and cut of the beret can also determine the rest of the outfit. For example, curved and flat berets like the one pictured, above go well with similarly curved apparel like the 3/4 sleeves and the bell skirt. On the other hand, more rectangular-shaped berets look nice with polo-necked tops and long trousers.

High-waisted skirts and traditional heels (you can pick some of the most discrete from our popular heels post) add to the vintage vibe.

A modern approach to the berets would be…

You also have endless alternatives to match the beret for a modern look. Adding newer fabrics and modern cuts to your combination will completely change the look your beret produces

Turtlenecks are one of the best choices you can make, but also cami tops, and even tank tops can work too.

For the lower body, a set of long formal trousers, tight jeans, or similar does the job. Note that smaller printed patterns (pictured above) are commonly seen as more modern and elegant.

Finally, go ahead and try a pair of ankle straps with your trousers if you wish a more formal look, or high boots when you are going a little bit more casual. With berets the possibilities are endless!

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Pillbox hat oufits

We know shift focus to another classic hat; one that is rarely seen today not only because its popularity peaked during the 1960s, but also because it is only used in formal (or at least semi-formal) outfits. The pillbox hat is one that will surely give your outfit a unique touch.

The hat style resembles an old pill case, and as it is shown with the next outfit, it matches with a wide variety of dresses. They are ideal for weddings, parties, or any royal family duties you may have 😉

Your pillbox hat will shine beautifully by portraying a silhouette that matches the hat’s, in other words, a straight and long figure goes well with the characteristic rectangular shape of the hat.

A tall and slim woman naturally portraits this, however, a woman that doesn’t match this description can still pull off this alternative.

Non-flared long skirts are perfect for doing this. Pencil skirts, draped skirts, and tulip skirts are all good options. Also, both low and high heels like pencil heels or kitten heels go along with these.

As for the tops, going for sleeveless or short-sleeved ones will further portrait that straight silhouette we are looking for. Jewelry and other accessories like necklaces and gloves add up to the elegance and traditional look.

A formal jacket that contrasts the top and combines with the bottom is optional but advisable.

Also, remember that dresses that fit the description above will work too.

One final thing to note: Matching the colour is essential to get the most out of the pillbox hat. Unlike the beret, an out-of-tune colour in the pillbox hat disrupts the flow and formality of the whole outfit, so avoid going this route. Moreover, matching the material/fabric of the hat to that of the top or bottoms is even better.

But this is not the only way to rock pillbox hats. Take a look at our next suggestion

As you can see, slightly flared skirts like A-Line or a knee-level circle skirt can work too. Try going for a cleaner or an embroidery print as opposed to a pleated skirt in order to maintain formality. Also, with these types of skirts, discrete ankle straps are welcome.

In the top, we are looking for an equally loose piece as the skirt (not too much though, and definitely not baggy). Similar fabrics and combining patterns will give you the freedom to choose short, medium, of full length sleeved tops

Pillbox hats are also widely praised when mixing with winter apparel such as coats, sweaters, and leg warmers below the skirt. Matching the colour and material of these would be key when going for it.

These are just some of the options pillbox hats open to you. We will bring different looks in the future, but if you can’t wait a good role model for pillbox hat fashion would be the Duchess of Cambridge – Kate Middleton.

Flapper headbands combinations

Flapper headbands were popular among aristocratic women in the 1920s and today can provide a unique look in most social events.

These headbands come in endless designs but all of them have certain traits that you can exploit.

The first one is its simple/innocent look; not only women from all age groups can wear it, but by doing so you can take a few years off your back 😉 this is because the headbands have a princess-like design that is commonly associated with children, so unconsciously people will perceive you as being younger.

Another important note is that flapper headbands usually come in very flashy colours like silver or gold. This makes it way easier and attractive to combine it with jewelry, gloves (both elbowed and standard), and similar accessories.

On the top, having printed and embroidery designs on top of the flashy colours makes it that much better. Sleeveless, tube tups, and other tops that expose your shoulders and arms give it a more fresh look.

The same story for the bottoms; below-the-knee skirts are a welcome addition, and due to the visual attractiveness of the outfit, you can go for more exotic designs like the pleated, tiered, or asymmetrical skirt.

Don’t forget that dresses simplify your selection and heels are a must!

Wear cartwheel hats properly

If there is one hat that has been overlooked in recent times, it is probably the cartwheel hat. Even worse is when people finally do wear them, but they do it horizontally and without realizing the hat’s proper position.

It’s true that modern cartwheel hats tend to be smaller or curved, but the traditional inclination when wearing them remains.

Also, don’t think that you need a traditional dress with gloves to make it shine; the following two examples are ways to combine this classic hat with a modern look.

As you can see, the hat goes well with formal T-shirt-like tops (with neck and without it) and pencil skirts, almost resembling an office look. This gives rise to a simple and comfortable yet elegant look. Even the high-heeled shoes are not essential to pull it off; a pair of low heels will do the trick.

You can play around with the top’s colours, prints, and cuts, but always maintaining the short sleeves and the V-neck (second outfit). Formal trousers are another alternative you have if you don’t feel like wearing skirts.

Finally, forget about expensive jewelry or flashy colours to make a statement with this outfit. A clean look not only looks amazing, but it assures that you don’t go over the top with the formality.

Bring back headwear on women!

The outfits presented here are just a tiny bit of all the universe of possibilities you have when choosing to wear headwear. The goal was to show you the potential that these (vintage) hats have, and that there are no excuses for you not to wear them. They looked incredible before and they still do!

Remember choosing the hats that best match your style and the occasion. Sadly, we cannot tell you which one works the best for you, but do know that there is at least one that does. Which one does the trick for you? Tell us in the comment section down below!

Also, don’t forget to check out our headwear review to know more about affordable, premium, and high-quality headwear available at different online shops.

That is all for now ladies! Take care and we wish for you to look your best with any headwear you try 😀


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