How to Style Your Sweaters, Jumpers and Sweater Dresses

While organizing a sweater outfit isn't exactly rocket science, you still should consider if you're looking your best in your sweater ensembles. I know I didn't until I made a thorough analysis on how famous fashionistas style them. Whether you're going to work, dinner, or just feel like effortlessly dressing up, a beautiful sweater combo is the way to go during those cold fall and winter days and even nights. There are definitely ways to dress up with a sweater and look appropriate even for a gala.

I want to start with more casual outfit ideas and then talk about dressy and super dressy.

Sweater and Jeans or Pants

Sweater and jeans is the most common and obvious casual outfit combo. Notice how upscale white jeans or pants look in combination with a sweater.

With White Jeans or Pants:

With Black Jeans Or Leather Pants

I like wearing colors with black anything on bottom. Even if it’s just a casual sweater in a fun color, adding black leather leggings or leather pants on bottom makes the outfit feel edgier and fashion forward. Whether with flats or heeled booties, jewelry or a hat – which I love with black leather pants for fall and winter – it just makes for a cute outfit!

With Colored pants

This look will be great either in complimentary colors like above or monochromic like below.


I need to confess my love for turtlenecks. They are so elegant and classy, and I have probably way too many. I fell in love with them as a teenager seeing pictures of elegant women in them. I wanted to look like them. Turtlenecks originate from medieval times when knights wore chainmail frequently. Chafed necks were the worst part, it prevented knights from turning their heads quickly in battle. A garment that could protect the neck and torso from the rough, heavy chainmail remedied the issue. Turtleneck evolved through centuries and in the 1940’s, 50’s and 60s is when the turtleneck really began to take off as the iconic basic we know and love today. Celebrities such as Jayne Mansfield and Audrey Hepburn helped to popularize this feminine, sexy version of the style.

So here is the modern take on turtlenecks

With Blue Jeans

The easiest casual outfit for fall and winter is to pair your sweater with skinny jeans. While the outfit isn't rocket science, as fashion doesn't need to be, its an easy outfit to throw on during the cold time of year. There are ways to look completely different while wearing a sweater and jeans. Wear this combo with pumps and matching purse to get a dressier look.

With Plaid Pants

Sweater + Pencil Skirt

This is one sexy way to wear an oversized sweater: pair it up with a pencil skirt.

It’s elegant, it’s fashionable and you will feel like you're on a runway.

From going to the office to attending a dinner with friends, this outfit is sophisticated and has a touch of elegance that makes it irreplaceable. Grab the pencil skirt of your choice and remember to tuck in the front of your sweater to emphasize proportion. Dress this outfit up with a pair of heels (or keep it casual with loafers) and make the day yours!

Sweater + Skirt

This option is feminine, pretty, and easy to pull off.

Sweater + Tulle skirt

Now, this is my favorite combination. I just think it’s such a great fashion hack to look the most stylish. It’s not a widely popular combo and if styled properly will make you stand out in the crowd.


Sweater + Mini Skirt

Sweater + Mini Skirt + Over the Knee Boots Combo

From suede boots to typical black ones, the look is versatile and it’s up to you to decide which one you’re feeling that day. Whether you’re wearing this outfit out for a date night or for a walk around the neighborhood, a sweater, a mini skirt and over the knee boots are the best combination of fun and flirty.

Sweater and Long or Maxi Skirt Combo (or a Slip Dress)

Some fashionistas are pairing sweaters with silk skirts or cool print skirts. I adore these combos. Often fashionistas style sweaters with silk skirts. 

Alternatively you can buy a silk or polyester slip dress and wear it with a sweater to get this elegant look.

Sweater and a Pleated Skirt

I adore this combo. Pleats are in fashion for 2019 and I also really like metallic pleated skirts. I also think a solid color sweater and an animal pattern pleated skirt is a great outfit idea.

Sweater and a Sequin Bottom Combo

Sweater + Shorts

Sweater + Gucci belt bag

Sweater dress + Over the Knee Boots

This combo is very popular with fashion bloggers. It has been popular for 6-7 years now since Stuart Weitzman's over-the-knee boots became a sought-after item. 

How cute a blue sweater dress and python print over-the-knee boots look. 

Sweater Dress and Pumps

Night Out

Sweaters, if dressed properly, can work even for a formal event.




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