HOW TO: Dress Like a Lady (Even if You Don't Behave Like One)

When you wear gloves to a bar in 2012, everyone thinks you are nuts and comments on them endlessly. These are 2 signs that your outfit has hit the mark.
Publish date:
July 10, 2012
shoppables, jewelry, fashion, style, shoes

My mother spent my whole childhood and teenage years trying to teach me basic etiquette and telling me when something wasn’t "ladylike." This equals probably one million times of her having to tell me something was "un-ladylike," as I have only brothers and was constantly falling out of trees, playing basketball barefoot, and stealing my dad’s company car to sneak out to nightclubs.

I have pretty good manners as a result of my mom's campaign of harassment. She also sent me to etiquette classes, where they not only taught me how to eat soup properly, (you move the spoon away from you, not toward you) they instilled in me the most important piece of etiquette advice ever given: There is no time that it’s okay to ask, “So, what do you do?” It’s very rude. Period. The world and all of polite society thanks you in advance.

“Being a lady” used to mean that you had to dress and act like Jackie Kennedy.


Jackie, as you may know, was the ultimate ladylike woman. Even after watching her husband be assassinated, she held it together.

November, 1963.

It is entirely possible for everyone to have a little bit of the grace Jackie had, even if you prefer to identify yourself as an uncouth heathen.

What goes with a classic Lilly Pulitzer dress? Freebie neon shades from the 80's and a Coors Light 'tall boy'.

My mother is quite pleased with the above photo, I'm sure. All her hard work has clearly paid off. See how I'm keeping my knees together like a lady even though I'm on a boat?

Even though I hated it at the time, my mother really did me a great service by making sure my etiquette was up to snuff. Knowing what to say and do in any situation has most definitely helped me get ahead in a brutal, make-your-own-luck industry. That's not to say I don't curse and belch and say some of the rudest shit you've ever heard. I just know how to behave when the situation calls for it.

Some people laugh at this as an antiquated idea, and New York senator Marty Golden sure got it wrong, but good manners and common civility are twin spinsters, lurching towards extinction. Life has become too fast and furious to bother considering other's feelings before acting. Discretion is out, because notoriety seems like so much more fun.

Miss Manners, aka Judith Martin, is my favorite authority on modern etiquette. Her advice is useful, current, relatable and hilarious.

Miss Manner's Guide to Excruciatingly Correct Behavior, $22.58,

Good manners are the start of ladylike style, but good clothes really do open all doors. It's easy to inject a little ladylike grace into your wardrobe without looking dated and stuffy. The trick to successfully making ladylike fashions seem fresh and new is to steal some touchstones from classic looks and then turn them on their heads.

Pearls are the very first thing I think of when someone mentions "ladylike style," but pearls mixed with spikes are an exceptional update of this classic:

Pearl and spike necklace, $30.00,

You can also take your own existing (boring) strand of pearls that you probably got for graduation, tie them in a simple knot, and add any charm you want that has a lobster clasp. Instant personalization and freedom from typicalness. Just make sure the charm is lightweight, so it doesn't put too much pressure on the silk cord.

Thanks for these, Mom & Dad.

I love a classic ladylike Chanel jacket, but will obviously never be able to afford one. Substituting a blazing red lace or psychedelic socialite style jacket for the classic tweed boucle jacket works better anyway. It's an instantly fresh, modern, ladylike look. A plain black lace slip worn as a dress + a crazy colorful jacket is one of my go-to summer standards.

Left, Red lace motorcycle jacket, $39.50, Right, Versace round collar jacket, $588.00,

You are all going to laugh at my next suggestion, but I like to wear crazy gloves out at night sometimes to give my outfits a little bit of ladylike flair.

Left, Polka dot gloves, $65.00. Right, Fuschia leather driving gloves, $88.00.

When you wear gloves to a bar in 2012, everyone thinks you are nuts and comments on them endlessly. These are 2 signs that your outfit has hit the mark. Grace Kelly would approve.

"Rear Window", 1954.

A classic 1950s-ish circle-skirted dress seems far more modern and fresh when it's sporting neon sleeves and is toughened up with a pair of "Creepers" and cute ankle socks.

Dress with neon acccents, $174.99,

Black studded "Creepers", $50.00,

Like Jane, I love the contrast between a delicate, girly dress and a clunky pair of shoes. Maybe I just never outgrew the 90s.

This little lace Peter-Pan-collared blouse is quite demure on it's own, and is perfect to wear to a proper lunch with your grandmother.

Cream lace blouse, $30.00,

You could also then turn around and wear it out at night with a black corset underneath for a bit of nasty but nice contrast. I love inherent trashiness when it's mixed with just the right amount of uptight fussiness.

Sheer black corset, $60.00,

A T-strap sandal always says "lady" to me, as does a powder-puff lavender color. The wedge heel with a subtle snakeskin print saves this pair from becoming too saccharine:

Pale lavender wedges, $129.00,

I think my whole affinity for ladylike style really starts and ends with a handle top bag. I love a purse that must be carried in your hand or in the crook of your arm, especially one that comes in a rainbow of colors:

"Edie" bag, $238.00,

Marni handle-top bag, $810.00,

My favorite ladylike style tip is also my last one: Invest in some vintage handkerchiefs. It is infinitely classier to pull a hanky out of your handbag rather than a crumpled tissue if the need to wipe your nose should arise.

Vintage handkerchiefs, $12.00-$52.00,



Twitter: @IveyAlison