It’s officially oversized sweater and leggings season! If you’re anything like me, you live for this cozy combination. It’s not only easy but versatile! From date night to everyday, I’m sharing the same oversized sweater and leggings four ways!

These days, I’m all about simplifying my closet. You don’t need a ton of pieces to create varying looks. It’s truly all about the accessories, and today’s outfits prove that simple changes can make a big difference!

The exact sweater that I’m styling is from my recent Walmart try on session! It was one of my favorite finds from that order. In fact, I bought it in two colors! You can see me style the camel version five ways in my oversized sweater outfit ideas post! It does fit true to size and is incredibly soft with a 100% cotton construction.

The leggings you’ll see in all of my outfits are my go-to classic Spanx faux leather leggings. If you’re looking for more ways to wear them, be sure to check out my five faux leather leggings outfits, eight spanx faux leather leggings outfits, and four more spanx leather leggings outfits! On to the oversized sweater and leggings outfits!

Classic Oversized Sweater and Leggings Outfit

If I want to keep my look classic, I tend to reach for a classic pair of flats. A loafer, ballet flat, or pointed toe flat are timeless options. A simple crossbody bag completes the look!

Trendy Sweater and Leggings Outfits

For a trendier look, it’s all about these lug sole chelsea boots! I added my felt rancher hat to keep the look on trend. Another cute (maybe slightly more casual) option would be to swap for a beanie!

Sporty Sweater and Leggings Outfit

For everyday mom-on-the-go style, you can’t go wrong with a sneaker and baseball cap. These trainers are a nice mix of classic and trendy with a thicker sole but all-neutral color scheme!

Dressy Oversized Sweater and Leggings Outfit

To take this look to date night, just add heels and some fun accessories. A red lip and statement earrings always takes a look up a notch! To complete the look, I added my all-time favorite foldover clutch.