10 Fashionable Ways To Wear A Pair Of Stilettos!!!

“Stilettos, Pumps, in the club, whoever thought these girls would get crunk” in the words of Diamond and Princess of Crime Mob, lol. Stilettos are sexy and a staple in many women and men’s closets.

They look great on pretty much any foot, however, you need to know how to walk in them, lol. A stiletto also makes your legs look longer and can overall enhance your whole look from head to toe.

You can wear stilettos casually, formally or even in a professional setting. Whether its pants, a skirt, romper or a formal gown, stilettos can work with pretty much any look. If you style them properly with the right outfit, you are sure to be a showstopper. Adding a pair of stilettos to your look instantly takes drab to fab!

Keep reading to see 10 fashionable ways to wear a pair of stilettos I virtually styled myself. I am going to show you how versatile you can be when wearing stilettos.

First of all, what the heck is a stiletto? You may be reading this and thinking why the hell should I want to know how to wear a stiletto. The definition of a stiletto is thin or spiked-heel as little as 0.9 inches in circumference and can be any height. That is also interesting because I always thought of stilettos as anything 6 inches or higher.

According to Popular Science, the rise of stilettos goes back to the 1950s. I find that to be odd because heels or the wearing of heels seem to go back farther than that. The reason being was because of men according to Popular Science.

Popular Science mentions that heels were originally worn by men only. So men wearing heels should not be something that is so Taboo, because it started with them.

In the 1950s when women started wearing heels, they wore the pointier version and then men wore the thicker heels. Men eventually dropped heels altogether and the stilettos continued to evolve for women. Fast forward to now, stilettos are seen as a way to lux up a look. The higher the better for some.

I personally love a woman who can walk in a stiletto pump. If she can dance in them it’s even better. Walking and dancing in high stilettos is a talent, trust me, I know, lol.

So now that we know exactly what a stiletto is and also a little background on it, we can get to the fun stuff!

How To Wear Stilettos To The Club

Shoes: Versace, Dress: BB Dakota, Bag: YSL, Earrings: Moda Operandi, Bracelet: Evans

This is how you stunt on em at the club! Strappy stilettos are sexy and this Versace stiletto has the charms on it to add visual interest. I kept the dress simple in this case because if I were to wear this, I would not want anything competing with the shoe.

How To Wear Stilettos To Work

Shoes: Jennifer Chamandi, Shirt: Helmut Lang, Skirt: Theory, Earrings: Farfetch. Bag: Zac Posen

This is the perfect way to add stilettos to your work look! It’s sexy but not too sexy where it’s inappropriate. With this look, it’s feminine but has a level of professionalism that commands respect. I can see a SheEO wearing this in a board meeting.

How To Wear Stilettos On A Date

Shoes: Saint Laurent, Turtleneck Dress: Paco Rabanne, Earrings: Farfetch, Bag: Michael Kors

This is the perfect look to make a good first impression on a date! It’s not overly revealing, but it showcases some skin to leave something to the imagination. You could pair this with the shorts showing if you wanted as well.

The stilettos themselves are simple but the patent leather look adds an edge to them. This look alone secures the bag for a second date!

How To Wear Stilettos To A Wedding

Shoes: Manolo Blahnik, Dress: Marchesa, Clutch, Judith Leiber, Bracelet: Suzanne Kalan, Earrings: Martin Katz

Wedding bells are ringing when I see this look here. Your not breaking any wedding etiquette dress wise with this, unless maybe the colors in the dress are the wedding colors. You should be fine still even if.

The shoes are definitely something I think is more appropriate for evening wear to an event. You may get just as much attention as the bride with this look, lol.

How To Wear Stilettos On New Years

Shoes: Jimmy Choo, Bracelet: Argento, Romper: English Factory, Earrings: Farfetch, Bag: Chanel

Bring in the New Year in style! This is a comfortable but sexy look that you can dance in all night! I believe anyone who wears heels should always have a pair of red stilettos in their arsenal. You can get so many wears out of them, so a good pair of red pumps is worth the investment.

How To Wear Stilettos To A Concert

Shoes: Christian Louboutin, Shirt: Ganni. Skirt: Moschino, Earrings: BaubleBar, Bag: Chloe

Rockstar chic she is! I love this look and I think it’s perfect to wear out to a concert or live music event. These Christian Louboutins are a piece of art. This look is an automatic backstage pass waiting to happen, lol!

How To Wear Stilettos To Girls Night Out

10 Fashionable Ways To Wear A Pair Of Stilettos
Shoes: Jimmy Choo, Earrings: Farfetch. Bodysuit: Alexander Wang, Shorts: Chanel, Bag: Loeffler Randall, Necklace: Elizabeth Cole

Where my girls at?!?! Its Friday, you girls want to go out and you’re not sure what to wear. This little number here would be a good option. This is another comfortable but sexy look.

A black pair of stilettos is a staple wardrobe accessory. You will be flicking men off left and right with this look, lol!

How To Wear Stilettos Casually

10 Fashionable Ways To Wear A Pair Of Stilettos
Shoes: Christian Louboutin, Bracelet: Nordstrom, Sweater: H&M, Jeans: Madewell, Earrings: Farfetch, Bag: Michael Kors

Who says you cannot slay when you are running errands? This is a simple look that can be put together easily for day to day activities. What I also like about this is, its cute enough to transition for a lunch date or even a Happy Hour.

I personally am trying to up my day to day looks. What you wear matters, I don’t care what nobody says. So a look like this would be ideal when not trying to do too much but doing just enough.

How To Wear Stilettos To A Upscale Event

10 Fashionable Ways To Wear A Pair Of Stilettos
Earrings: Farfetch, Shoe: Just Cavalli, Bodysuit: Intermix. Skirt: GCDS, Coat: Alberto Makali, Bag: J.W. Anderson

If you struggle with piecing together looks for upscale events, this is a good example of a look you can wear. The shoes are staples, so I let those shine with this look here. Everything else is solid colors, yet they are stylish.

When in doubt, if you have a staple shoe, that is always a good start for an upscale event. Use your shoe as a base to build your look when you have a staple.

How To Wear Stilettos To A Job Interview

10 Fashionable Ways To Wear A Pair Of Stilettos
Bracelet: Allsaints, Shoes: Casadei, Shirt: Baum und Pferdgarten, Pant: Nordstrom, Earrings: Arias, Bag: Stella Mccartney

Dress for Success! I think this look would be great for a job interview. Now, of course, you would want to do research on the job and dress code, etc.. However this look is professional and the shoe compliments it perfectly.

Also, now that most colors can pretty much be worn year-round, the Yellow color should not be an issue.

Mission Complete

So there you have it! 10 fashionable ways to wear a pair of stilettos served on a platter. These are just examples of ways to wear them. You, of course, may come up with many many more.

Also, I used pretty high stilettos in my examples in all my looks. By definition remember, a stiletto can be as little as 0.9 inches, so you can have a smaller heel. I side-eye that definition though, lol

Last time I checked, a 0.9-inch heel is a kitten heel, lol. Whichever way you style them or the heel height, have fun with styling them. Do take it too seriously. Confidence is important, so be confident in any decisions when purchasing or wearing stilettos.

You also want to make sure you can walk in stilettos as well. I advise practicing walking around the house wearing stilettos if you never wore them before. You can also do this to break them in.

If you want to know some ways to style knee-high boots, you can check my post here for some help with that. I hope you got some inspiration and ideas for the looks I have curated. My goal is to help anyone who wants to slay fashionably on all levels at all times. Thank me later and don’t be a stranger!

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Stilettos can be worn in many different settings. Click see 10 fashionable ways to wear a pair of stilettos I virtually styled myself. #stilettoheels #heelsoutfits #heelsclassy
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