1. Faux Leather Leggings
It took me a season to get into the faux leather leggings a few years back, but now I’m all in! I love them as an option between basic black leggings and black jeans. I’ll wear them from dressed down in an athleisure outfit to dressed up with a pretty blouse, moto jacket, and heeled booties. They’re versatile and add a bit of an edge to any outfit.
For this particular pair, I recommend sizing up one from your typical size.
Item Shown: Spanx Faux Leather Leggings
2. Heeled Weatherproof Booties
While my need for winter boots has been removed almost completely by my move to North Carolina, I still like to have a pair or two on hand! I used to wear heeled booties all the time in Chicago, so I’m happy to have a pair that I love here, too. They’re functional and it’s nice to have the heel if you want to dress them up a bit. You will catch me wearing them with leggings most often, but they work with jeans, too!
Item Shown: Dolce Vita Huey H2O Waterproof Bootie
3. Sherpa Pullover/Jacket
A winter closet staple, if you ask me! I love a cozy pullover like this to throw on anytime of the day. I usually pair one with leggings and sneakers, but you could definitely do jeans and booties or white sneakers. The added warmth is key!
Items Shown: Aerie White Sherpa Quarter Zip, Gap Purple Sherpa Jacket (similar option), Aerie White Button Cloud Sherpa (similar option)
4. Cozy Oversized Sweaters
Based on item number one, this shouldn’t be surprising. While an oversized sweater isn’t the most flattering thing in the universe, I won’t quit them. I wear them with leggings and my skinny jeans – I like to balance an oversized top with a fitted bottom. These can easily be layered over and you can wear anything from sneakers to heeled booties with them!