How to Wear Dresses + Skirts in Winter

The winter season is the perfect time to breathe new life into your warmer weather essentials, like dresses and skirts. Layering your favorite winter accessories over your dresses and skirts can make fab winter outfits! But, if you are feeling a little underwhelmed with what is currently in your wardrobe, I am here to show you that the fabulous outfits you want, already exist in your wardrobe. If you are ready to learn how to wear your dresses and skirts this winter season, meet me on the next page to check out the perfect fall outfit combos my blogger boos put together! 




1. Skater Dress + Beanie + Tights + Combat Boots

I guarantee you that your summer skater dress is waiting in your closet waiting to be styled this winter. Pairing easy winter accessories like beanies, tights and boots with your dress will give your look the winter sass you need.


2. Tunic + Treggings

Treggings, leggings and tights are a great way to keep your legs warm no matter the outfit you put together. But, please make sure your top is long enough to cover your booty ... we want to look sophisticated and polished (not trashy).

Taniqua, Taniqua Russ

3. Printed Skirt + Graphic Tee + Blazer

This has to be one of the chicest and easiest ways to maximize your winter wardrobe! To give your look a little bit of glam, rock your tee and skirt with a sequined blazer and velvet pumps. 


4. Tweed Mini + Blouse + OTS Blazer

OTS, short for over the shoulder, is all the rage right now and looks good with any outfit! If you are looking for a causal work wear look, pair your business casual skirts with a relaxed top and chic classic blazer worn OTS.


5. Striped Dress + Sweater Vest

Warm up a summer dress with a sweater vest and cute booties! 

Ashley, Fab Ellis (Sweater Vest)

6. Check Print Maxi + Lace Up Boots

Maxi skirts are great way to keep your legs covered! But, when you rock a pair of cute booties it gives your outfit a fall appropriate look!

Yah'Zahara, The Nspiyahd Life

7. Pleated Skirt + Vintage Sweater 

You can never go wrong with vintage! But skirts & sweaters are the perfect pair for the winter season, no matter the clothing era they were created in.


8. Leather Midi + Turtle Neck + Fur Vest

Leather skirts are the epitome of chic especially when worn with a fur vest!


9. Sequin Skirt + Plaid Top

Sequins and plaid are an unlikely pair, but they are super cute to wear this winter season. Adding a bit of glitz to a casual look will instantly give your fit a chilled vibe.


10. Denim Midi + Layered Outerwear

Denim skirts look chic when paired with layered outerwear. Try rocking your denim skirt paired with a light weight sweater vest, followed by a leather jacket (Princess is slaying in this deep green leather). 

Princess, Personal Bravery

11. Layered Mini Dress + Vest 

Layer your favorite mini/midi dresses with a long sleeve button down top for a preppy professional ensemble. Add a long hem buttoned vest over your dress and button down for an added layer of chic and warmth.

Ashley, Fab Ellis 

12. Swing Dress + Tights 

Long sleeve swing dresses are the perfect basic pieces for the winter! Add your favorite opaque or printed tights with your swing dress for a warm and easy look! 


13. Cords + Camel Coat

Rock your favorite cord sets with a pair of pumps and camel coat (or peacoat of your choice)! Now, depending on the area you live in, you may need to add a pair of opaque tights and a scarf to warm up this look.


*I do not own these photos. Each beauty featured in this post gave me written permission to use their photos.

Which looks are your favorite?