What commenters have asked me in the past is to write more about when and where a hat is appropriate, and how to pair them with outfits. This is hard information to impart, but I shall do my best.
I'm starting with my felt hat collection because it is winter and it is easier to get away with a felt hat in winter. Felt hats, in general, are better for evening wear and late afternoon to evening weddings. Color and decoration also plays a role, and the different hat styles give an aura of different retro time periods. Selecting a hat shape is a little like choosing glasses or getting a haircut.
Definitely a cold weather item. You have to be cautious with the cloche, many face shapes have a hard time carrying off this much head coverage. Trust your instincts. I tend to think heart and oval shaped faces can carry this hat off best. If your face is too round, you can end up with a lamentably bowling ball look. But not always, this will also ride on your facial features. Also whether the cloche has a brim or not. Color is also key as there is little hair between the hat and your complexion, so choose with care. I rarely wear my black cloche without a lot of makeup.
An undecorated cloche, like the ones above is more casual and day wear, I wouldn't wear one to a wedding unless heavily decorated. The best thing about a cloche? It's your solution to a bad hair day.It will give you a 1920s ~ 1930s look.
Pair this hat with menswear-inspired looks or classic 1930s style knitwear.
The Pork Pie
This hat has certain advantages. It can be found big or small, and it can be seated towards the front or the back of the head, tilted at a jaunty angle or worn straight on. It works for either day or evening (although if black I'd pair it with a bright color for day) and is formal enough for a wedding. It will, as a rule, elongate the face, so keep that in mind. If you have a long oval face this hat is probubly not for you. However, it does have a very retro feel, and it has yet to be embraced for any kind of modern aesthetic. So wear it and you will have the aura of the 1950s - 1960s about you. Also your hair should be done, it doesn't look good with long loose hair (with the exception of the utterly mod pixie cut). You'll probubly need a hatpin.
Pair this hat with girly 1950s full skirt dresses or prim pencil skirts and pencil dresses for the Mad Men secretary look.
Berets, even with Prince in on the action, will always give one a bit of the French chic, if you ask me. I vastly prefer a felt beret to a cloth one. I like the more sculpted look and because my hair is short, felt hats stay in place better. I almost always wear mine tilted. And I am just as likely to wear it with a modern outfit as a vintage one.
I think these hats are timeless. The are cold weather hats, though, and they don't actually provide much warmth. They are a little casual for a wedding or evenign event but paired with the right formal attire one might get away with it.
Pair with a-line skirts (not too short or you head into school-girl territory!) and striped tops for ultra French chic, or with wide sailor pants and metal buttons for a slight military table. Also looks nice with print and knit dresses.
The best thing about this hat is that is sticks close to your head, like a hairband, and thus I believe most any face shape can carry it off. It comes in a range of sizes, I prefer one that hugs the crow so it won't fall off.
I tend to think of this hat as ranging over time, but most of the images I found were from the 1950s. I wear my red one a lot as it also packs easily, and I love red accessories. I adore this hat so much I don't confine it to any season or time or occasion. I don't wear it when it's really hot, it is, after all it is felt. But that doesn't stop me from wishing I could!
Pair this with anything girly, not the best hat for menswear or pants.
The Drape (with Corners)
This is one of my favorite hat shapes. It has a crown section that fist tight to the head and then a curled and corner front brim that is almost beret-like in feel. Like the beret, I think it looks best worn at a jaunty angle and not right on top or at the back of the head. Again I feel this style has a certain French chic, but they are quite 1940s-1950s in feel.
Good for day or night, and the occasional special occasion. I've never seen one worn with long loose hair, but I imagine it would be nice. The triangle corns are not for everyone, again you have to watch the fact shape with this hat. I can't advise since I've only seen it on my own head or in pictures.
Treat it a little like a beret to be on the safe side, when pairing it with looks. Although I also use it where I might use a pork pie.
1960s Hubert de Givenchy hat via The Costume Institute of the Metropolitan Museum of Art
The Lady's Fedora
A friend of mine once said that there is nothing sexier than a woman in a man's hat. I've never felt I could carry off the fedora, so I don't own any, but I do tent to agree with him.
Late at night, Hugo Loosers Party, Melbourne in Mur's hat, 2010.
My guess it that this suits a round or a square face best, and larger features. But I know many a small pert little thing who can rock the fedora, so in the end, it's just a difficult hat. Be careful, it can be hoochie rather than retro if not paired properly.
This hat has come in and out of fashion for women almost as often as it has men, 1940s and 1960s in particular, and there there was at 1990s debacle we won't talk about.
Wear it with coverage menswear (not too much skin or too tight!) or with structured shirt dresses for the best retro look. Think film noir.
1961-1963 Hubert de Givenchy hat via The Costume Institute of the Metropolitan Museum of Art
The Sun Hat
Or the felt floppy hat, became suddenly popular recently. I blame Rachel Zoe. Women who like to hide behind their hair love this hat. (Was that catty? Oh well.) It's got a very 1970's flavor. I do love the idea that you can get protection from the sun in winter with this hat, and that's when it's appropriate ~ sunny winter days.
Pair it with maxi dresses and skirts, long and flowing, boho chic. Not my thing and likely to be out of style soon. I've tried it on more than one occasion. But when I wear modern clothing, I still prefer structure, and this hat has never worked with my look. Odd, as I have plenty of floppy straw sun hats. The same rule for straw sun hats apply to this one, if you don't have the head shape and features to carry off big with aplomb, no amount of hair or massive glasses are going to make up for it. Nash.
Want something like this to wear to an outside winter wedding? Go for the stiffer and more highly decorated version, like so . . .
1920 Half-Mourning Hat (worn with a veil) The Meadow Brook Hall Historic Costume Collection
The Follie, Fancy, or Small Perch
Don't be mistaken, this hat is silly. Which is possibly why I love it. I'm looking for the perfect emerald green felt one to add to my collection. I have a few modern straw follies, but no felt vintage as yet. You can find them in places like Ross, cheap, attached to headbands. You can make them yourself quite easily out of shoulder pads. I like them best perched far forward on the head. This hat will work for a wedding, tea, prom, any special occasion.
Pair it with a cute flirty dress or a full skirt and knit top.