skirt with tights outfits

20 CUTE WINTER OUTFITS FOR SCHOOL 

Looking for the perfect back-to-school outfit ideas for this fall and winter? Whether you’re gearing up for college, university, or high school, there’s something here for everyone! With the holidays almost over, it’s time to start thinking about your back-to-school wardrobe.

Planning your outfits in advance can save you time each morning, especially during that first week when you have so much else to focus on. The last thing you want to stress about is what to wear.

If you haven’t decided on your first-day outfit or mapped out your looks for the first week, here are 20 stylish ideas to inspire you!

CUTE WINTER LOOK WITH SKIRT 

A cute winter look with a school skirt that combines warmth and style in an easy way. Pair a cozy knit sweater with a solid or wool mini skirt. Finish the look with knee boots or a trendy scarf to keep you warm but still look stylish in colder weather.

HAPPY SPORTY LOOK

Here’s a fun athleisure look for school that blends comfort and style, perfect for active days. Start with solid joggers or leggings and a lightweight zip-up hoodie for a bright outfit. Finish it off with trendy sneakers and some fun accessories to add your own touch while staying ready for any adventure!

MOM BLUE JEANS

Mom blue jeans are a versatile choice for a school outfit, offering both comfort and a relaxed fit. A trendy cropped sweater or a classic tee complements them for a laid-back yet stylish look. Adding fashionable sneakers and a crossbody bag completes the ensemble, making it perfect for everyday wear.

GREY SWEATPANTS

Grey sweatpants are a cozy and stylish option for school wear, providing comfort for long days. Pair them with a matching hoodie or a tight T-shirt for a balanced look that is both comfortable and polished. Complete the outfit with trendy sneakers and a backpack to stay comfortable while still expressing your personal style.

COZY JACKET

A cozy jacket is an essential addition to any school outfit, offering warmth and style as the seasons change. Choose a fleece-lined or denim jacket to layer over a simple tee or hoodie for a chic yet casual look. Pair it with jeans or leggings and your favorite sneakers to create an effortlessly cool ensemble that keeps you comfortable throughout the day.

OVERSIZED SWEATER AND LEGGINGS

Ah, the classic “I woke up like this but still look fabulous” outfit. An oversized sweater with leggings feels like a cozy hug all day long. Go for a chunky knit in a neutral color for ultimate comfort and style. Pair it with knee-high boots, and you’ll be all set for that 8 AM class. Pro tip: Choose fleece-lined leggings for added warmth—your legs will definitely thank you

PLAID SKIRT AND TURTLENECK

Embrace your inner Cher Horowitz with this preppy-chic look. A plaid skirt paired with a fitted turtleneck gives off major “smart cookie” energy. Keep warm by layering with cozy tights or knee-high socks, and top it off with a blazer for extra warmth and a dash of sophistication. Who says you can’t ace your chemistry test while looking like you stepped out of a ’90s rom-com?

PUFFER VEST AND JEANS

Let’s talk about the unsung hero of winter fashion: the puffer vest. It’s like wearing a cozy sleeping bag in public without any judgment. Style it with your favorite jeans and a long-sleeve tee for a look that says, “I’m ready for anything—whether it’s a pop quiz or an impromptu snowball fight.” Bonus: The pockets are perfect for stashing hand warmers. You’re welcome!

SWEATER DRESS AND KNEE-HIGH BOOTS

Who says dresses are only for summer? A sweater dress is basically a cozy blanket, but make it fashion. Pair it with some stunning knee-high boots for a look that’s both comfy and chic. If it’s extra chilly, throw on some thick tights for warmth. It’s the ideal outfit for days when you want to look stylish but still feel like you’re wrapped up in bed.

LAYERED TURTLENECK AND DENIM JACKET

Layering is essential for winter fashion, and this combo is a total winner. Start with a turtleneck (your neck’s new best friend), then add a denim jacket, and voila! It’s like wearing a cozy hug, but with a cool edge. Throw on some jeans and sneakers, and you’re ready for the day. Pro tip: Keep a beanie handy for those extra chilly days. Bad hair day? Not anymore!

CROPPED SWEATER AND HIGH-WAISTED PANTS

Who says you can’t show a little skin in winter? A cropped sweater and high-waisted pants strike the perfect balance between cozy and chic. Opt for a thick, chunky knit to stay warm, and style it with wide-leg trousers for a look that says “fashion editor on a coffee break.” Finish it off with ankle boots, and you’ll be strutting through those school hallways like it’s your own personal runway.

SHACKET AND JOGGERS

Let’s talk about the shacket—the perfect blend of a shirt and jacket that’s become a fashion must-have. Style it with joggers for the ultimate comfy-cool vibe. It’s basically like wearing pajamas to school, but totally acceptable. Throw on some chunky sneakers, and you’re set for whatever the day brings.

SWEATER VEST AND BUTTON-UP

Channel your inner grandpa (but make it fashion) by layering a sweater vest over a button-up shirt. It’s preppy, cozy, and the perfect way to look smart while staying warm. Add some jeans and loafers for a look that says, “Yes, I did finish the extra credit assignment.” Push up your sleeves for that effortlessly cool vibe. Glasses are optional, but highly recommended for maximum scholarly style.

TEDDY COAT AND SKINNY JEANS

Wrap yourself in a teddy coat and enjoy the sensation of being embraced by a very stylish bear. Combine it with skinny jeans for a sleek silhouette. This outfit is ideal for those days when you want to feel like you’re still in bed but need to adult. Slip on some ankle boots, and you’re ready to take on the day!

TURTLENECK DRESS AND OVER-THE-KNEE BOOTS

Want to feel like a total boss babe? Slip into a turtleneck dress and over-the-knee boots. It’s sleek, chic, and warm—what more could you ask for? If it’s particularly chilly, add some tights and throw on a long coat for maximum drama as you walk into class.

COLORFUL PUFFER JACKET AND LEGGINGS

Who says winter has to be all doom and gloom? Brighten up those dreary days with a colorful puffer jacket. Style it with leggings for a look that’s part “ready for the gym” and part “human ray of sunshine.” It’s like wearing a mood booster, and you’ll never lose your friends in a crowd again!

FLANNEL SHIRT AND CORDUROY PANTS

Nothing says “cozy winter vibes” quite like a flannel shirt and corduroy pants. It’s like wearing a warm hug all day long. Roll up the sleeves of your flannel for a laid-back look, or button it all the way up for extra warmth. Add some combat boots, and you’re ready to take on the world (or at least that group project). Fun fact: Corduroy pants create a satisfying “swish” sound when you walk. Instant ASMR, anyone?

SWEATER BLAZER AND PLEATED SKIRT

Want to look put-together without sacrificing comfort? Meet the sweater blazer. Team it with a pleated skirt for a look that’s part academic chic and part cozy queen. Add some warm tights and loafers, and you’ll be ready to ace that presentation (or at least look like you know what you’re talking about)!

TURTLENECK SWEATER AND LEATHER SKIRT

Want to mix cozy with edgy? Try a soft turtleneck sweater with a leather skirt. It’s like your top half is ready for a nap, while your bottom half means business. Add some sheer tights and ankle boots for a look that’s part “I’m here to learn” and part “I might head to a concert later.” Word of caution: This outfit may inspire you to strike poses in reflective surfaces. Embrace your inner model!

LONG SLEEVE SWEATER DRESSES

Long sleeve sweater dresses are a cozy and fashionable choice for school, providing warmth and style in cooler weather. These dresses can be easily dressed up or down, making them versatile for various occasions. Combining them with ankle boots or sneakers and a denim jacket creates a chic yet comfortable look that’s perfect for everyday wear.

CONCLUSION

Winter doesn’t have to mean sacrificing style. With the right pieces and a little creativity, you can create adorable and cozy outfits that are perfect for school. From classic sweaters and jeans to trendy puffer coats and boots, there are countless options to explore. Remember to layer up for warmth and don’t be afraid to experiment with different colors and textures.

19 MOST TALKED-ABOUT KYLIE JENNER OUTFITS OF ALL TIME

Each of the five Kardashian-Jenner sisters has had their own fashion journey. Kim loves a sensual style with a sporty touch, Kourtney has moved from trendy to grungy, Khloe favors stylish activewear, and Kendall’s model-off-duty look is clean and chic. Kylie Jenner’s outfits, however, are often more surprising than her older sisters’.

From bold colors to body-hugging styles and simple French-girl looks, you never know what Kylie will wear next. We love that she keeps us guessing! While her sisters have clear styles, Jenner enjoys trying out different looks, and with so many designers available to her, it makes sense to mix things up.

Kylie Jenner’s outfits—whether on the red carpet or in everyday life—offer lots of fashion ideas for everyone. To help you keep track of the beauty mogul and mom of two’s best looks, we’ve picked out some of our favorites.

KYLIE JENNER IN L.A. IN AUGUST 2018

The Kardashian-Jenners are all about that Barbie vibe, and Kylie is definitely no exception. It’s hard to pick what we love most about this look—the stunning dress, the chic shoes, or the sleek platinum ponytail!

KYLIE JENNER AT THE MTV VMAS IN 2018

There’s no need to tell you that the business owner and founder is a boss; this sharp blazer dress outfit speaks for itself.

KYLIE JENNER IN N.Y.C. IN NOVEMBER 2018

Why go for denim-on-denim with separates when you can nail the Canadian Tuxedo look with a stylish jumpsuit? This all-denim outfit is definitely one we can support.

KYLIE JENNER AT THE GRAMMY AWARDS IN 2019

Balmain suits Jenner perfectly, as shown by this blush pink jumpsuit with dramatic sleeves she wore to the Grammys. We imagine this one-piece is as comfy as it is beautiful; it’s a nice change from her usual body-hugging dresses, and we love it!

KYLIE JENNER AT THE MET GALA IN 2019

At one point, Jenner had a purple phase. She brought back her signature color for the 2019 Met Gala and perfectly captured the “Camp: Notes on Fashion” theme.

SOPHISTICATED SEXY

For the premiere of Travis Scott: Look Mom I Can Fly, Jenner chose an outfit that exuded sophistication. The white bodycon dress highlighted her signature curves, while the sexy back cutouts added a fun twist. We also loved the addition of the bow choker!

KYLIE JENNER AT THE ‘VANITY FAIR’ OSCAR PARTY IN 2021

This mermaid-style gown from Ralph and Russo combines sparkly fun with Old Hollywood glamour. Jenner said the look was worth it, even though it made sitting down a bit tricky!

KYLIE JENNER IN L.A. IN MARCH 2021

Is it just a coincidence that Jenner wore a strikingly similar outfit to celebrate the Haqq sisters’ birthday in 2023, just like she did in 2021 at the same venue? The only difference is the color: red instead of black. It just goes to show that even celebrities repeat outfits—sort of!

KYLIE JENNER AT THE BALMAIN SHOW AT PARIS FASHION WEEK IN SEPTEMBER 2022

Having designer friends definitely pays off, especially when they create exclusive looks just for you. Jenner has been a muse for many designers, but this crochet minidress by Balmain’s Olivier Rousteing is one of our top five favorites.

KYLIE JENNER IN PARIS IN SEPTEMBER 2022

Jenner is a strong supporter of the underwear-as-outerwear trend. She paired white hipster briefs with a matching tank top, black tights that blend into her boots, and a grey overcoat on top—simple yet absolutely showstopping!

KYLIE JENNER AT THE THE BOF 500 GALA IN PARIS IN 2022

Jenner is no stranger to a mesh look, but this outfit from the Business of Fashion 500 gala in Paris last fall really caught our eye. Custom-made for her by Casey Cadwallader, the creative director of Mugler, it features a stunning design of asymmetrical lace.

KYLIE JENNER AT THE COPERNI SHOW AT PARIS FASHION WEEK IN SEPTEMBER 2022

Although Jenner has recently been seen in more neutral tones, she’s always been “a big fan of color,” as Lizzie McGuire’s Miranda Sanchez would say. She particularly shines in blue, making the floral minidress she wore front row at the Coperni Spring/Summer 2023 show a must-have on this list. Don’t miss the matching sunglasses and heels!

KYLIE JENNER IN N.Y.C. IN NOVEMBER 2022

Jenner has certainly influenced many street style trends, but we think she may have borrowed the no-pants look from her big sister Kendall. Regardless, she nails the leggy style with a neutral base, an oversized black trench coat, and pointed-toe heels.

KYLIE JENNER IN ARCHIVE MUGLER AT THE MUGLER COUTURISSIME OPENING IN N.Y.C. IN 2022

At the Mugler Couturissime exhibition opening, Jenner called herself the “Mugler king” on Instagram. Given that it’s been almost a year since the event and we’re still talking about her look, we definitely agree! The Morticia Addams-inspired corset dress is fabulous on its own, but her headpiece would have turned heads even without it.

KYLIE JENNER IN PARIS IN FEBRUARY 2023

Remember when Jenner experimented with bright pastel hair colors? Well, blue is still her go-to! For an afternoon stroll in Paris, the mom of two wore a long-sleeved, body-hugging midi dress in a striking blue shade, pairing it with glittering Barbie-pink boots.

KYLIE JENNER IN L.A. IN MARCH 2023

It’s no surprise that for Malika and Khadijah Haqq’s 40th birthday, the youngest Jenner celebrated in style. The Kylie Cosmetics founder dazzled in a sexy set featuring a satin miniskirt and a matching black satin peek-a-boo mesh top. She completed the look with a leather trench coat, sheer black tights, and pointed-toe heels.

KYLIE JENNER IN MAISON MARGIELA AT THE ‘VANITY FAIR’ OSCAR PARTY IN 2023

Maison Margiela custom-made Jenner’s stunning metallic gown for the 2023 Vanity Fair Oscar Party, and the design did not disappoint. The original piece featured a statement bow tied at the bust and a cape train flowing from her mid-back. The only way this look could have been better is if the beauty mogul arrived in the Batmobile, because it’s definitely giving “superhero, but make it fashion.”

KYLIE JENNER IN JEAN PAUL GAULTIER AT THE MET GALA IN 2023

If anyone knows how to make a statement on the red carpet, it’s Kylie. The Haider Ackermann for Jean Paul Gaultier gown she wore to the 2023 Met Gala turned heads with every step. With its asymmetrical neckline, cold shoulder, and high thigh slit, this fiery ensemble was undoubtedly one of her best looks.

KYLIE JENNER IN PARIS IN MAY 2023

Jenner made a splash in the quiet luxury trend while in Paris. The reality star wore a crisp white midi dress with a corset waist and matching heels, keeping her accessories simple with small silver hoops, black sunglasses, and a tiny white handbag.

CONCLUSION

Kylie Jenner’s impact on the fashion world is undeniable. Her bold, daring, and often trendsetting outfits have captivated audiences worldwide, cementing her status as a style icon. From her early days as a reality TV star to her current role as a successful businesswoman and influencer, Jenner’s fashion choices have continued to evolve and inspire.

The outfits featured in this list represent just a glimpse of Jenner’s extensive style repertoire. Her ability to seamlessly blend high fashion with streetwear, her willingness to experiment with bold trends, and her knack for creating iconic looks have solidified her place in fashion history. As Jenner’s career continues to flourish, it is clear that her influence on the fashion industry will only grow stronger.