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Layering 101: Dress With Style In The Winter Months

Posted on October 29 2019

Layering 101: Dress With Style In The Winter Months

The winter months will be here before you know it. Fall has hit in full swing, bringing along the chilly season. As the winter months begin to surround us we want to make sure that you are prepared to look your best. I've taken the liberty of putting some layered looks together to have you looking stylish while staying warm.

For more casual days, we have a sporty look that is guaranteed to have you looking fresh. Start the look with a basic beanie, ASOS has quite a few for a decent price. 

Next, you can take a fitted turtle neck (black, single-toned, or multi-toned) and layer it under a t-shirt. I recommend layering your turtle neck under our Simply Dripping signature tee. The black Simply Dripping tee has multiple colors in the graphic that will make it super easy to match with any turtle neck.

Puffer coats are next up in the look. You can either wear the coat open or closed, depending on the weather that day. This puffer from Forever 21 Men comes in black and tan so it can match whichever look you're going for. You can also check out our past puffer coat blog for more finds. 

These Jordan sweats and Adidas originals are the final pieces that will pull this look together.  Feel free to play with color schemes and change it up as need be, but this comfortable look will have you warm all winter long. 



Our Simply-24 Hours Curved Hem tee provides the perfect base for a street look. The bright white color of the shirt and long hem will contrast dark denim for a classic yet edgy style. 

Pair the dark denim jeans with either a black leather sherpa jacket or a sherpa-lined denim jacket to keep the contrast between the light-colored shirt. Levi's provides two quality jackets in their signature trucker fit style. Finish off the look with a pair of Chelsea boots of your choosing. 

Now onto the ladies:

Depending on your day, you can be looking for either a warm comfortable outfit to throw on to brave the weather or a fashionable look to turn heads on the street. I'll start out with an athleisure look that is guaranteed to keep you comfy and warm. Part of being warm and comfortable is wearing over-sized clothes. Champion has an oversized zip-up that I want to wrap myself up in. 

Underneath the zip up, you can start your base layer off with our Simply Imagine Signature tee and a classic pair of black leggings. The long hem of the t-shirt and a pair of high-waisted leggings will keep you comfy for those on the go days. 

To finish off the look, throw on a pair of Doc Martens and head on out the door.

For your more fashionable days, start off your look with our Simply Secret Crop. You can pair this crop with high-waisted jeans or trousers depending on what look you're going for. The high-waisted jeans will give your look a more mainstream style while the trouser can give you a whimsical edge 

A pea coat thrown over your shoulders and a long scarf will give you the warmth you need and really make your outfit pop. I suggest rocking a black pea coat and light-colored scarf will keep some vibrancy in your outfit.


To finish off your look, add some chunky booties. You can either stick to the classic black bootie or pull some colored booties to match your scarf for a coordinating statement piece look.