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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.

THESE ARE THE 10 BEST SHOES TO WEAR WITH LEGGINGS

Leggings are a wardrobe staple for many reasons: they’re comfy, versatile, and can be dressed up or down. But what to wear with them? The key to taking your leggings from lounging to chic is all about what you pair them with. Get ready to elevate your legging game! Here are the 10 best things to wear with leggings.

OUR TOP PICKS 

KITTEN HEELS

Ditch the sweatpants and elevate your leggings in a snap with kitten heels! These comfy lifesavers are the perfect way to instantly polish off a casual legging look. Unlike sky-high stilettos, kitten heels offer all-day comfort so you can conquer your errands or transition effortlessly from daytime adventures to evening plans. The low heel height creates a effortlessly put-together vibe, and for an extra touch of sophistication, pair them with stirrup leggings that hug the ankle.

TRAINERS

Forget the struggle of choosing between comfort and style. Trainers and leggings are the ultimate power couple in your closet. This dynamic duo is perfect for your most relaxed days, offering unbeatable comfort for running errands, hitting the gym, or simply lounging in style. The sporty edge of trainers adds a cool vibe to your leggings, while the breathable fabrics of both pieces keep you comfortable and moving freely. But don’t be fooled by their casual nature – trainers come in a vast range of styles, from sleek and minimal to chunky and bold. Whether you choose a timeless white trainer or a trendy platform sole, you can easily dress your leggings up or down. Throw on a denim jacket for a laid-back look, or elevate things with a blazer and statement earrings for a touch of athleisure chic. Leggings and trainers are a win-win for both comfort and style, offering endless outfit possibilities for any casual occasion.

BALLET FLATS

Channel your inner Parisian with the effortless combination of ballet flats and leggings. This chic duo offers the perfect blend of comfort and style. The sleek lines of the flats complement the clean silhouette of leggings, creating a polished yet casual ensemble. Both pieces are known for their comfort, allowing you to move freely and stay cozy all day. The versatility is unbeatable – dress them up with a flowy blouse and blazer for work, or keep it casual with a tunic top and denim jacket. Don’t forget to accessorize! Play with textures and patterns – a chunky knit cardigan or statement necklace adds personality. Animal print flats or metallic finishes can inject a touch of fun. Ballet flats and leggings are a foundational outfit combo that every wardrobe needs, offering endless possibilities for both casual and semi-formal occasions.

LOAFERS

Ditch the sweats and add instant polish with loafers and leggings! This surprisingly chic combo takes you from casual to effortlessly put-together. The structured silhouette of loafers elevates your leggings beyond loungewear, making them work-ready for casual Fridays or even a night out. Loafers come in a range of styles, from classic penny loafers to chunky platforms, so you can match your vibe. Pair sleek loafers with a crisp white shirt for preppy chic, or go edgy with chunky ones and a leather jacket. Don’t worry about sacrificing comfort for style – loafers can be surprisingly comfy, especially with a well-cushioned sole. Want to add a playful touch? Channel your inner fashion icon and show a sliver of patterned socks. Prefer a clean look? Go sockless! Loafers and leggings offer the perfect blend of style and comfort, making them a versatile choice for any casual or semi-formal occasion.

FAUX FUR ANKLE BOOTS

Embrace cozy vibes with faux fur ankle boots and leggings! This pairing is perfect for adding a touch of luxury and warmth to your outfit. The soft texture of the faux fur booties complements the sleek lines of leggings, creating a look that’s both stylish and comfortable. Dress it up with a chunky knit sweater and a midi skirt for a cute fall outfit, or keep it casual with a tunic top and a denim jacket. No matter how you style them, faux fur ankle boots and leggings are sure to keep you warm and fashionable all season long.

HIGH HEELS

Level up your legging game with a classic pairing: high heels! This combo exudes confidence and instantly elevates your look from casual to night-out ready. While stiletto heels are a bold choice, consider pumps with a thicker heel for added comfort. The key is to balance the proportions – pair pointed-toe heels with opaque leggings for a streamlined silhouette. Play with textures! Leather leggings add a touch of edge, while patterned heels can inject personality. Don’t be afraid to accessorize – a statement necklace or clutch can take your look from day to dressy. High heels and leggings offer endless possibilities for a polished and confident look.

CHUNKY BOOTS

Chunky boots and leggings are a fashion match made in heaven. This pairing offers a perfect blend of comfort and edgy style. The chunky sole of the boots adds personality and balances out the sleek silhouette of leggings. It’s an ideal choice for cooler weather, keeping your legs warm while making a bold statement. Dress them up with a longline coat and a chunky knit sweater for a cozy yet chic look, or keep it casual with a graphic tee and a denim jacket. No matter your style, chunky boots and leggings will add a touch of cool-factor to any outfit.

PATENT SLINGBACKS

Dress up your leggings with a touch of sophistication! Patent slingbacks are the perfect partner for adding polish and a hint of retro flair. The sleek shine of the patent leather complements the clean lines of leggings, creating a look that’s both modern and elevated. The slingback style keeps things comfortable, while the subtle heel adds a touch of femininity. Play with proportions! Pair pointed-toe slingbacks with opaque leggings for a streamlined silhouette, or embrace a wider leg legging for a more relaxed vibe. Don’t be afraid to experiment with color – classic black is always chic, but a pop of color in your slingbacks can add personality. Accessorize with a statement necklace or a structured bag to complete your polished look. Patent slingbacks and leggings offer a versatile choice for elevating your casual style or adding a touch of class to a night out.

KNEE HIGH BOOTS

Knee-high boots and leggings are a timeless fashion combo that offers endless outfit possibilities. The boots add instant polish and sophistication, transforming your leggings from casual wear to a put-together look. Whether you choose sleek and fitted boots or slouchy and relaxed styles, they’ll flatter your legs and keep you warm in cooler weather. Play with textures! Leather boots add a touch of edge, while suede offers a softer vibe. Experiment with heel heights – flats are comfy for errands, while heels elevate your look for a night out. No matter your style, knee-high boots and leggings can be dressed up or down, making them a versatile choice for any occasion.

METALLIC KITTEN HEELS

Inject some glam into your leggings with metallic kitten heels! This unexpected pairing elevates your outfit beyond casual while remaining comfortable. The subtle sheen of the metallic heels adds a touch of personality without being overwhelming, while the kitten heel keeps things comfy for all-day wear. This combo is perfect for brunch with friends, a night out, or even work on a casual Friday. Play with textures! Pair your metallic heels with sleek leather leggings for a polished look, or embrace a more relaxed vibe with a matte jersey pair. Don’t be afraid to experiment with color – classic gold or silver is timeless, but a bolder shade like rose gold or emerald can add a real statement. Metallic kitten heels and leggings offer a fun and stylish way to elevate your everyday look.

SHOES TO WEAR WITH LEGGINGS: DOS AND DON’TS

Leggings offer a comfy and versatile option for guys too. But just like with any outfit, there are a few things to consider when choosing shoes to pair them with. Here’s how to elevate your legging look:

DO

Embrace comfort and style! Sneakers, trainers, and loafers are all great choices. They complement the slim silhouette of leggings while keeping things casual and cool. Boots, especially chelsea boots or chukka styles, can add a touch of edge and work well in cooler weather. Play with proportions – balance out the leggings with chunky soles or opt for a tapered jogger style for a more relaxed vibe. Don’t forget to accessorize! A beanie, cool watch, or statement bag can add personality.

DON’T

Forget about coverage. If your leggings are thin or see-through, layer with a longer top or opt for a thicker, opaque fabric. Super bulky shoes can look out of place, so stick to sleeker styles or those that complement the overall look. Comfort is key – avoid uncomfortable shoes or excessively high heels (if you’re feeling adventurous!). Finally, remember that leggings are a casual piece. Avoid overly formal settings or situations that require dressier attire.

FAQ

1. What can I wear with leggings to work (on a casual Friday)? 

Dress them up with a blazer, blouse, and loafers or ballet flats.

2. Are leggings good for working out? 

Yes! Leggings are a popular choice for exercise due to their flexibility and breathability.

3. What tops look good with leggings? 

The options are endless! Try tunic tops, longline tees, sweaters, or even flowy dresses for a layered look.

4. Should I wear socks with leggings? 

It depends on the shoes and weather. Socks with loafers or slingbacks can be trendy, while boots might require them for warmth or comfort.

5. Are sheer leggings okay? 

For a polished look, it’s best to avoid sheer leggings or pair them with longer tops or opaque tights underneath.

CONCLUSION

Leggings are a wardrobe workhorse for a reason. With their versatility and comfort, they can be the foundation for countless stylish looks. From dressed-down casual to surprisingly chic, leggings can be transformed depending on what you pair them with. So, don’t be afraid to experiment and find your favorite combinations! Whether you’re rocking sneakers for errands or turning heads in metallic kitten heels, leggings can be your key to effortless style and comfort.