35 Cute Preppy Winter Outfits
New season means preparing new outfits and organizing your wardrobe. Winter may mean having to wrap up warm, but that doesn’t mean you can’t be trendy. In fact, winter style is cozy, yet even more stylish thanks to layering. Don’t believe us? Read on to discover how to work those winter pieces with these inspiring must-have cute winter outfits and trends!
1Babe In Black
All black is elegant, cozy and flattering on all body shapes. It is a slimming color that will highlight all your best bits. For rainy days, celebrities run straight for Hunter boots, but if you are a girl on a budget, Asos have the most gorgeous rubber boots to go with your outfit. Beige is the perfect choice for a hint of color as it is sophisticated and compliments the black perfectly.
2Nice In Nude
It may be getting chillier, but that doesn’t mean you can’t wear light colors. Nude is a color that can be worn all year round and makes you look glowing, even on the coldest of days. Nothing can beat a good white sweater and jeans combo, but the nude accessories make the outfit. A beanie hat with a ridiculous pompom will be your best friend this winter!
3Down To Earth
Winter style can still be casual. Velvet slip-ons add texture to the outfit, and you can’t go wrong with a beautiful navy blue. Loose-fitting jeans make this stunning look a bit more casual and comfortable on a day-to-day basis. They sit perfectly on the hips and are perfect for girls with a boyish frame. A chic saddle bag is an accessory you should invest in this winter.
The tomboy/androgynous look can still work in winter. Ripped straight leg jeans teamed with your favorite hoodie (or your partner’s) can still look stylish with a boyfriend coat thrown over the top. White sneakers brighten up the look and bring it down to Earth. Curl your hair for a fun and playful look.
Dare to bare this winter? Why hide those gorgeous legs this winter? Unless the temperatures are below freezing, then go for it! The turtle neck is a key winter piece around which you can focus most of your winter wardrobe. Don’t be afraid to recycle some of your summer pieces – tuck it into a corduroy skirt for more texture. Your trusty dark blue denim jacket will cover you up without swamping you.
6Fab And Feminine
One of our favorite jackets to wear in winter the biker jacket. Whether it is in leather for those warmer spells or in suede to warm you up, it is a wardrobe staple. We have our eye out for one like this in blush pink for the winter! It is a soft color that will warm up your skin tone and compliment your wardrobe. The details of the rest of the outfit work perfectly with this girly color for an understated, yet feminine look. An oversized sweater can be worn with intricate lace bracelets for a little bit of detail. The jacket pulls the whole look together for a super cute street style.
7Ring The Alarm
Red was the color of summer 2017, but it isn’t quite over yet! Red is not only festive but flatters any skin tone and makes the most understated of outfits dressy. This outfit is perfect for the office, proving that sweaters can be glamorous and smart. Red velvet heels allow you to show off a bit of leg and elongate your frame – score!
Winter means layers, but they can still ooze elegance and make you feel sexy. A classic turtle neck with a patterned pencil skirt mix timelessness and modern trends for a flawless outfit. A chic and loose-fitting duster coat finishes off the look, and let’s face it – in navy blue, looks even smarter!
Everyone’s favorite – the shearling jacket – is back this season. It is thick, warm, and will take anything the weather throws at it. This twist on the biker jacket is the perfect statement piece, so keep it simple underneath. A tee and jeans combo will never let you down. Loafers are still in this season, so throw on a pair for easy yet trendy wear.
Soft dove gray gives a chic finish to a monochrome outfit. A gray suede biker jacket with silver details will compliment the silver buckle on the belt and give a sophisticated finish. We would complete this look with white sneakers, or black and silver sneakers (like the new Chanel collection) for the ultimate casual outfit.
11Lady In Leopard
The leopard print coat is the face of many winter collections this season – Topshop, Rebecca Minkoff, and Maje – so get on the bandwagon too! It is the statement coat of the season, and for girls who love black and green, these colors will work wonderfully with the vibrant print. For a simple, laid-back look, throw a leopard print cocoon coat over a black sweater and cropped jeans. The gold details from the loafers suit the light browns from the wild print. We need this coat in our lives!
12Sweater Dress Weather
The sweater dress is so easy to throw on. It is effortless but oh so stylish. To wrap up warm, bloggers like In The Frow love teaming this sweater dress with knee-high boots for a sophisticated and cozy look. The gold details work perfectly with the camel coat, which makes the look even more sophisticated. Curls will make the look date night ready!
We love this sweater dress. It is slouchy, casual yet has a sexy side with the slits to show a bit of leg. Make it instantly smart with a camel coat and a smart black leather handbag. The outfit is versatile, wear it with sneakers for a sporty/casual vibe, or team it with black heeled boots for a dressier occasion.
If you want to dress to impress this winter, a midi skirt is going to be at the top of the wishlist. A turtle neck sweater tucked into a pink pleated midi skirt is girly yet chic. The pleats give the skirt graceful movement, making the outfit feminine and chic. A black biker jacket will give the look a rockier edge, and pink metallic heels will make sure the feminine feel doesn’t get lost.
We love Parisian minimal chic. Jeans, ankle boots, and a striped shirt can be graced on the streets of Paris, so grab some inspiration from our European friends. Ripped jeans make the look more modern, and the fedora finishes off the look and adds texture to the outfit.
16Beautiful In Blue
Mix street style and business women for the ultimate working girl look. An oversized boyfriend coat will be your go-to item this winter. Flattering Mom jeans with a rip at the knee give a more modern edge to this working girl style, and a hint of red brings the look into 2017. Oversized sunnies are a must, so what if it’s winter?
We can’t get enough of dungarees. They are comfortable and add a playful twist to your outfits. We love this outfit over a basic striped tee for a no-fuss look. We would team this with white or pastel pink sneakers to brighten the outfit up. A messy bun will finish off the casual look perfectly.
Sports luxe was one of the up and coming trends this year. It is perfect for girls who love their hoodies but still want a feminine look. Hailey Baldwin knows how to rock sports luxe on the streets. Her favorite hoodie, with an oversized bomber jacket, give an androgynous feel, and while jewelry and skinny jeans still flatter your body shape.
19Pop Of Pink
You may not be going to the Fashion Weeks, but that is no reason not to dress like you are. We love this tailored bright pink coat, which is ideal for blondes! Embroidered jeans with a hint of bright pink pull this look together and bring it from basic to fabulous. Doc Martens and a choker make the look rockier and edgier in a flash! If you want to make it very feminine, then we recommend swapping the Doc Martens for nude heels.
20Fabulous (Fake) Fur
A (fake) fur coat will keep you snug but make your look dramatic. Black is great on blonds, although we do recommend dove gray on brunettes. Ripped hem jeans are right on trend, and add texture to an outfit. A slouchy turtle-neck sweater is a perfect top to tuck into these jeans, and the camel boots give a western vibe.
21Teddy Coat Cuteness
If you love cozy and thick coats, the teddy coat is another alternative. Teddy coats are a great way of making outfits a bit more laid-back. Pleather pants and a white shirt should be dressy, but the pink teddy coat makes it street style appropriate. We would finish the look off with white slip-on sneakers to match the white shirt.
22Dare To Bare
It may be chilly outside, but that is not a reason to not dress to impress. A maxi denim skirt with a daring thigh slit gives graceful movement and makes a casual look sexier. A camel turtle neck makes the look luxurious and feminine. Black heels elongate your frame and flatter your calves.
Winter gives us a great excuse for layering! Just take a look at this retro British inspired look. A trapeze-shaped pinafore dress is ideal, just slip one of your favorite shirts underneath. It is timeless, elegant, yet with a biker jacket is brought into the modern day.
Turtle neck sweaters can be worn with pretty much everything – as you can see here, it looks amazing even with a fake leather look skirt. The sweater has more shape tucked into the skirt, and the outfit in itself is very figure-flattering. Vamp it up with black and gold accessories and black heels for the perfect date night outfit.
25Little Bit Of Leopard
As we mentioned before, leopard print is a trend you should rock out this winter. If you are a little shy, bring it into your look gradually. Leopard print heels give a rock glam edge without over-facing yourself. An olive green cocoon coat compliments the print perfectly.
Another Parisian-inspired look for you this winter. A striped turtle neck sweater and jeans seem like a simple enough outfit, but teamed with a navy blue peacoat, has a military-inspired vibe. Navy blue and camel make quite the pair, and camel accessories are ideal to finish off the outfit.
Blush pink is a flattering color for all skin tones, and unlike nude pinks, doesn’t wash out some skin tones. It brings a healthy glow to your skin and makes your look feminine. This outfit is preppy, a sweater tucked into a pink midi-skirt and pulled in at the waist with the Gucci belt of dreams, mixes luxury and high street for a Gossip Girl inspired look.
Dark brown is often overlooked, but this winter, it is making its come back. Dark brown dungarees in corduroy have a luxurious feel, yet are still super casual. A light gray sweater makes the perfect companion, and white Converse keeps the look playful and youthful.
Who says you can’t wear all black? Ripped jeans show off just the right amount of skin, and a khaki parka and Timberlands give an androgynous feel, playing on the masculine/feminine vibes. The black hood makes the look dramatic and striking, and the black handbag is a must-have for any girl!
A shearling coat is a cozy statement piece that is ideal for you hipster or vintage lovers. It compliments a simple outfit and keeps you warm and snug all day long. A fedora makes the look hip and indie-inspired, and black boots still allow your coat to be the center piece. The cherry red saddle bag adds a pop of color.
Lilac is a color you can still rock this winter. Thrown over a monochrome outfit, lilac will stand out and keep the look fresh and modern. It also can be worn with various colors such as beige, pastel pink, white and dove gray. Here, the coat has been teamed with beige and camel accessories for a softer look.
A fedora is one of our favorite ways to hide that bad hair day! Ripped jeans and an oversized sweater are items everyone should have in their winter wardrobe. For those days you aren’t ready to face the world, throw these pieces on, and you will be able to face anything! A dark brown satchel is a glamorous addition to a laid-back outfit.
We want to get our hands on this ombré sweater. In pink, it is instantly feminine, and the high-low effect is very flattering. An oversized scarf with threads of pink running through it is the best winter accessory to pair it with. Clashing gold jewelry will be striking against the subtle tones of this outfit.
Another style of pinafore dress is this midi dress. It nips you in at the waist and in black, is ideal for an important meeting. Slip a white shirt underneath for school girl vibes and a patterned clutch will turn your look from drab to fab. Mule heels allow you to show a bit of skin and still make you feel elegant.
35Black and white
This look features an elegant high waist black and white stripes pants and an off-shoulder white fluffy long sleeve knit jumper. Jazz it up with silver or gold accessories and black statement belt.
Wear your black skinnies with white or baby pink sneakers, with black bomber jacket (with gorgeous fur trim!). Don’t forget to spice up your look with a matching beanie!