Today marks the start of Old Navy’s big 50% off Friends and Family sale! Their prices are always pretty reasonable, but now they’re can’t-miss! It’s the perfect time to fill in holes of your winter wardrobe, grab gifts, or even put together your family photo outfits!

I did things a little differently this time. I tried on fifteen different items and ended up creating nearly 30 different outfits with them! But if you still want more Old Navy reviews, be sure to check out my Fall Old Navy Try-on session from just a few weeks ago for even more! For sizing reference, I am 5’7.5″, a size 30/10 and a medium. I will list exactly what sizes I’m wearing for each item. Let’s go!

**If you did not receive a 50% off coupon code via email, text VIP to 653689 to get sent your 50% off code via text message**

Turtleneck Sweater + Vest + Button-front Jeans

This turtleneck is one of my favorite finds. It’s very soft, has a cool texture and the perfect oversized fit. I’m in a medium. It also comes in three other colors. I love it layered up with a vest, like this quilted puffer! I’m also in a medium in the vest but recommend sizing up one. The vest comes in seven colors!

Lastly, these jeans! They are a straight leg cut and slightly cropped. (Again I’m 5’7.5″) They are very stretchy, so I suggest sizing down one!

Turtleneck sweater (medium) | Vest (medium) – size up one | Jeans (10) – size down one

Plaid Top + Stripe Sweater + Vest + Button-front Jeans

These Old Navy plaid tops are staples. I love this holiday plaid print. (You’ll get a better look at it further down! ?) A fun way to layer it is with a lighter weight crewneck sweater. The stripes are a fun print mix that work since the incorporate the same colors as the plaid.

Plaid top (medium) | Stripe sweater (medium) | Vest (medium) – size up one | Jeans (10) – size down one

Mock Neck Dress + Sherpa Jacket / Long Cardigan / Vest

A basic swing dress is a wardrobe staple. This one has a mock neck and ribbed texture. The only one I saw in store was in a small tall and that actually worked for me. I would suggest sizing down one.

I show it layered three ways. The sherpa jacket is super-cozy and comfortable! If you don’t love blush, it also comes in tan. This is a great alternative to a faux leather or suede jacket.

This long cardigan is one of my favorite finds. The material is a nice substantial fabric and amazing quality! It comes in three other colors, but I love this jewel tone. With the cranberry it’s a more sophisticated holiday pairing!

Of course it also works with the vest! My main advice would be just to keep your vest a more tailored one. A large puffer vest is better suited for more casual looks. You could also go with a sweater vest!

Dress (small tall) | Sherpa jacket (medium) | Long cardigan (medium)| Vest (medium) – size up one

Mock Neck Dress + Turtleneck Sweater / Crewneck sweater

Throwing a sweater over a lighter dress is a great way to add warmth and interest to an outfit. Both the turtleneck and crewneck work here! I would prefer this look with booties or boots to balance out the top.

Dress (small tall) | Turtleneck sweater (medium) | Crewneck sweater (medium)

Chambray Dress + Long Cardigan + Vest + Sherpa Jacket

A chambray dress is just as versatile as a swing dress! In fact, I think it is a little more wearable since it is season-less. You can style it all the same ways I did the swing dress above!

Dress (medium) | Long cardigan (medium)  | Vest (medium) – size up one | Sherpa jacket (medium)

Chambray Dress + Turtleneck Sweater / Crewneck sweater

Layering with a shift-cut dress is even easier than with a swing cut. The more tailored skirt creates a less bulky figure and more tailored silhouette. You can also throw on a sweater to define your waist.

Dress (medium) | Turtleneck sweater (medium) | Crewneck sweater (medium)

Chambray Dress + Stripe Sweater + Vest

These might be my favorite looks I created. This is the type of outfit that would work well in a business casual environment as well as the weekend!

Dress (medium) | Stripe sweater (medium)  | Vest (medium) – size up one

Plaid Top + Long Cardigan + Black High Rise Jeans

This is the same plaid top from above. If you wanted to make it work-friendly, I’d pair it with a nice long cardigan and a skirt of slimmer cut pants. To make it a little more feminine and trendy, knot the bottom into a bow!

Now, let’s chat these jeans. They are so flattering on! I love the high rise and that they come all the way to the ankle on me. (5’7.5″) I recommend staying with your true size.

Plaid top (medium) | Long cardigan (medium) | Black Jeans (10)

Plaid Top + Stripe Sweater + Vest + High Rise Black Jeans

Again I layered with a stripe sweater. I also love the addition of the beanie! It’s one more print in the mix, but again, it works since we’re staying in the same color family.

Plaid top (medium) | Beanie | Stripe sweater (medium) | Vest (medium) – size up one | Black Jeans (10)

Plaid Top + Stripe Sweater + Shearling Jacket + High Rise Black Jeans

Shearling jackets are very on-trend right now and this one is perfect. The shearling is super-soft and makes the jacket so warm. I also love that the sleeves are unlined making it easy to move your arms and without adding bulkiness. My store only had a large and I didn’t mind the fit! If you’ll be layering with heavier sweaters, size up.

Plaid top (medium) | Shearling jacket (large) | Stripe sweater (medium) | Black Jeans (10)

Tunic Plaid + Long Cardigan / Crewneck sweater + High Rise Black Jeans

Although this plaid is labeled as a “tunic length” it definitely wasn’t on me. In fact, I didn’t find it any longer than the classic button down plaid from above. If you want to wear it with leggings, I suggest sizing up! Also, this one is collarless, which is perfect for those of you who don’t like anything tight around your neckline. It still works perfectly for layering!

Tunic plaid (medium) – size up for longer length | Long cardigan (medium) | Crewneck sweater (medium) | Black Jeans (10)

Turtleneck Sweater + Sherpa Jacket / Shearling Jacket + High Rise Black Jeans

Another way to wear that turtleneck that I love! Again, it comes in three other colors! The gray came home with me.

Turtleneck sweater (medium)  | Sherpa jacket (medium) | Shearling jacket (large) | Black Jeans (10)

Sherpa Pullover + Beanie + High Rise Black Jeans

I couldn’t help but try on a pullover! They look so cozy– and they really are! If the bold buffalo plaid isn’t your style, it also comes in several solids. There are also matching options for kids! I’m in a medium, and although it fits true to size, I would have preferred a large for a true oversized fit. You could go either way, depending on the fit you’d like.

Sherpa (medium) – TTS but I’d prefer a more oversized fit | Beanie| Black Jeans (10)

Fair Isle Sweater + Vest  + Sherpa Jacket + High Rise Black Jeans

Lastly, I grabbed this fair isle sweater. They are such a classic for winter and this one has metallic silver thread, making it holiday-appropriate. I did try it layered with the plaid and found it too much for my taste. I’d layer it with chambray or a solid button down! It also looks adorable with vests and jackets.

Sweater (medium) | Vest (medium) – size up one | Sherpa jacket (medium)  | Black Jeans (10)

Black and White Sweater

This sweater is the same as the gray textured crew neck as above but I didn’t have a chance to try it on in store. It’s very comfortable and perfect for layering! You could wear it all the same ways I styled the white and black wider stripe option previously! Fit is relaxed. I’m in a medium!

Sweater (medium) | Jeans (not Old Navy) – TTS | Boots (9 – TTS) under $40!

Teddy Coat

This coat is a crazy-good value! The material is textured like a teddy bear and so soft. I love that it’s also stretchy, making it perfect for layering! It also comes in pink!

Coat (medium) | Sweater (medium) | Jeans (not Old Navy) – TTS | Boots (9 – TTS) under $40!

Be sure to also check out my Fall Old Navy try-on from October!!