Businesswoman, model, and recently labeled as a “climate criminal,” Kylie Jenner is the most followed woman on Instagram, with over 300 million followers. The twenty seasons of the reality TV show Keeping Up With The Kardashians introduced her to a world of luxury, fashion, and a very broad audience that follows her life on social media and throughout Hulu’s show The Kardashians.

Kylie is the youngest of all Kardashian-Jenner sisters (Kourtney, Khloe, Kim, and Kendall), but she didn’t take long to develop her own fashion style and establish new trends. In 2015, Kyle introduced Kylie Lip Kits with lots of help from Momager Kris Jenner. The product became so successful that Kylie launched an entire cosmetics brand that has expanded to a wide range of cosmetics and skincare products.

Throughout the growth of her brands, Kylie has given major fashion statements that serve as inspiration for her followers. Today, we’ll take a look at a few of her iconic outfits and how we can use them as inspiration and adapt them to our own style. 

Lesson 1. Don’t be scared of cut-outs

An outfit that consists of an asymmetrical red top with matching pants. Image Courtesy of Kylie Jenner.

Cut-outs can be edgy, sexy, attractive, and bold. Cut-outs come in all sizes and proportions and can be placed in any part of the body. It’s particularly common to see this feature placed somewhere in the neckline or the back, so it is way more interesting whenever you find it in another area. 

Kylie wears an asymmetrical red top with one sleeve. The sleeve has several interesting cut-outs with tiny silver beads that bring the top to a whole new level.

These kinds of tops are very easy to use, and with the right accessories, you can wear them for a long time, making several in-style and exciting looks. 

There is a shade of red for every woman. Audrey Hepburn. Image Courtesy of Kylie Jenner.

Lesson 2. Love Classic Prints

Kylie leverages fashion when taking photos to promote her cosmetics. Image Courtesy of Kylie Jenner

After every fashion show and every fashion season ends, we start to see new prints introduced by fast fashion. A couple of years ago, pineapple motifs were everywhere, reaching a peak quickly where everyone got tired of them, and now we barely see them. Other motifs such as mustaches, owls, and avocados have gone through this quick cycle of gaining massive popularity and mainstream attention, becoming a brief trend that loses popularity within a matter of months.

So in order to invest in good quality printed clothing that we like and that we can wear for a long time without feeling exhausted from seeing it after a couple of weeks, we must focus on classic prints. Classic prints include polka dots, floral motifs, plaids, and geometric patterns that we see all year long, year after year. Designers may play with the colors and proportion of these prints season after season, there may be a collection that brings particular attention to one of these prints, but overall, they are timeless.

Kylie Jenner’s aesthetic is now truly recognizable among stylists and other celebrities. Image Courtesy of Kylie Jenner.

Kylie’s full houndstooth catsuit is a great way of wearing a classic print. The colors and the proportions make the whole outfit easy to style with other accessories. Houndstooth becomes particularly popular during the autumn and the winter, with coats, sweaters, and scarves that have this print. You may see color variations of houndstooth, but black and white is the most common version of it.

Lesson 3. Make Monochromatic Different

Kylie Jenner’s white dress for the Kardashians premiere in April 2022. Image Courtesy of The Kardashians. 

How do you wear a full white outfit and stand out in a crowd that most likely loves white as much as you do? The answer: Make it as interesting as possible with texture and accessories.

 Kylie wore an all-white latex Coperni look for The Kardashians premiere. The dress featured a very subtle cut-out at the chest, some floral details, and a very interesting slit showing matching boots custom made by the same designer. In Coperni’s fashion show, the model who wore this design styled it with red pumps, but Kylie’s footwear choice seems more interesting, futuristic, and memorable.

Monochromatic looks can be very fun because you don’t have to worry about color harmony; trying clothes and accessories of the same color until you see something interesting that you feel comfortable wearing. Sometimes a necklace, a nice bag, a cool hat, or even a spectacular eyeshadow can be the determining factor between hating and loving your outfit. 

Lesson 4. Office Wear can be cool

Kylie Jenner’s outfit for The Kardashians press day. Image Courtesy of Kylie Jenner.

Even before the pandemic, the dress code for workplaces started to move toward a casual setting. With several workplaces encouraging flip-flops and comfortable clothing for long work periods, this general trend is only becoming more prominent and diversifying to multiple interpretations. For some, casual work attire means jeans and sneakers. For others, formal attire is still required and important for the work.

However, there is a nice subtle variation of officewear that is slightly more relaxed, and with the right styling, it can be appropriate in several workplaces. Oversized blazers and trousers with ease can be styled to look sophisticated yet more comfortable than tight skirts and tailored blazers. This is how Kylie Jenner reinterpreted officewear during the press day of The Kardashians on Hulu in Malibu, California. The silhouette seems inspired by sportswear, but by making it all white and styling it with jewelry and a pair of pumps, the look is elevated and modern.

Kylie Jenner dressed up with white baggy pants and a blazer for a press day. Image Courtesy of Kylie Jenner.

Lesson 5. The Oversized Shirt is truly versatile

An oversized pink can be styled to be appropriate for several occasions. Image Courtesy of Kylie Jenner.

Several factors have influenced the popularity of the oversized shirt. Many people got used to wearing very comfortable clothes (pajamas and loose pants) during the stay-at-home orders. The transition to “normal” clothes has been challenging for many. Maybe it’s a matter of weight gain or simply getting used to these clothes again. This is why many people love oversized shirts, a comfortable way of dressing up without contouring the body.

Oversized shirts can be long enough to be worn as a dress. Depending on the occasion, you can also style it with a skirt, a pair of shorts, jeans, or formal trousers.

Kylie wears an oversized hot pink shirt with black high heels to go to work at the Kylie Cosmetics headquarters.

Lesson 6. Black and White Forever

On May 5, 2018, Kylie Jenner’s casual outfit broke the internet. 

When we fall in love with a color combination, we begin to have a varied collection of items from these colors. This translates to more toys to play with and more possibilities to dress up.

The timeless and always stylish black and white duo can be interpreted in all kinds of styles, from girly and soft, to bold and loud. With all the accessories and clothes available in black and white, it’s easy to create a wide variety of outfits that will stimulate your creativity to keep playing with them. With headpieces and sunglasses during the warm seasons and sweaters, boots, and gloves during the cold days, it’s hard to go wrong with black and white. Since this combination has a nice harmony, you can add accessories, textures, and layers. Kylie wore a black tank top, a white cut-out hoodie, and black baggie pants in New York City back in 2018. Still, the outfit looks current, and each of the pieces can get along with other black and white garments to create more exciting combinations. 

Lesson 7. Do your homework​​

Kylie Jenner's Fashion Style adapts to themed parties, like her outfit for Adidas Pop-Up Shops. Image Courtesy of Adidas Originals.

When people put together themed parties and social events, there’s a lot of work to do. There are invitations to send out, food to serve, music to play, decorations to purchase, and employees to hire. One of the best ways we can be grateful when we are invited to this kind of party is to dress as the theme suggests. When you arrive without a bathing suit at a pool party, it may be interpreted as if you don’t want to have fun at this event. But when you arrive at a Halloween party with a wig, a costume, and an attitude to be silly, you appreciate the effort that went into planning the whole party, 

So taking the time to plan your outfit for a party is an important task. Doing your homework and asking about the location, the vibe, the reason for the party, and who the other guests are will make a huge difference in how you will feel when you arrive at the party and how the others will perceive you.

If you are the host of the party, the responsibility is even bigger, because if you don’t take them seriously, how can you expect that the party’s guests do?

On November 29, 2018, Kylie Jenner and Adidas hosted an opening party. Adidas footwear display aligned with the gas station them of the pop-up shop. Image Courtesy of Hollywood Reporter.

When Kylie Jenner was an Adidas ambassador, she threw an opening party for the Adidas Gas Station Pop-up event. There were pink and purple candies all over, simulating a convenience store at a gas station. The shoes were displayed in what looked like typical convenience store fridges. There were also lottery tickets where people could win $10 off when purchasing selected Adidas items. Kylie wore a black and white printed dress inspired by racing flags, aligning her attire with the atmosphere of the event. 

Lesson 8. Full print is the new monochrome.

April 10, 2021. Kylie Jenner’s Outfit of the Day. Image Courtesy of Kylie Jenner

For over a decade, the Kardashians made fashion statements with monochromatic looks. Kim relied on black dresses for most red carpet events, then there were a few years with nudes and greys where Yeezy started to get global attention. So after exploring monochromatic looks with several colors, there comes a need to explore other alternatives. This is how fashion designers started to create more collections that included clothes, bags, and footwear with the same color or the same print. This gives you an opportunity to wear all the pieces together and then style them separately but still with a certain harmony and sophistication. 

Kylie wore this full Bottega Veneta look on April 10, 2021. Top, trousers, shoes, and bag all belong to fashion designer Daniel Lee’s vision of wearing this blue and burgundy print from head to toe. Daniel Lee worked as the creative director of Bottega Veneta from 2018 to 2021. He created iconic pieces for this brand that were celebrated by major celebrities, such as the Kardashians and Jenners.

Social media posts can be a source of inspiration whenever it feels like we are staying behind with fashion trends and life. Regardless of labels and budget, all this free fashion information we find online is a great way to understand better where fashion trends are coming from and where fashion is going. The upcoming fashion trend for the next six months may already be on your Instagram feed. 

Lesson 9. Take clothes out of context to make them interesting.

Kylie Jenner wore a denim jumpsuit and grey wig for a night out. Image Courtesy of Kylie Jenner.

Go to a rock n’ roll concert, and you’ll see lots of black clothes and leather. Go to a New Year’s Eve party, and you’ll see sequins, metallics, and lots of shiny black clothes. When you dress like the rest of the people around you, it can be challenging to stand out. This is why it’s becoming common for celebrities and other fashion leaders to take clothes out of context and make them interesting.

What if you wear sequins during the day for brunch with your friends? What if you go to that rock n’ roll concert with a bold color that reflects the roughness of the music but still is different from what most of the audience is wearing?

Some occasions give you the opportunity to be playful and take clothes out of context. Of course, when dress codes are instructed, as happens with weddings, workplaces, and many events, it would be disrespectful to wear something that doesn’t align with the dress code required.

But when it comes to social events, hanging out with friends, and taking photos for social media, there’s quite enough room for creativity,

In 2018, when denim jumpsuits and overalls became a huge thing, you started seeing people wearing them in farmers’ markets, shopping centers, vineyards, and activities that, for the most part, happen during the day. Kylie Jenner decided to wear a denim jumpsuit with a grey wig and high heels and make this jumpsuit an outfit for a casual night out with friends, where dress codes were not required, and cameras were ready to capture the moment.