Skip to content

Capsule Wardrobe Remix: How to Wear the Convertible Sweater Four Ways

**Press play to watch the video!**

Happy Monday!

Exciting news–I just discovered that some of my favorite items from last year are back in stock with exact or have new updated versions! ?? This post was one of your favorites last year, so I wanted to give it a refresh!

In this post, I’m showing you how to wear one of my favorite sweaters four different ways. (This is also a similar new version of it this year!) My exact one I’m wearing in this post is also still available but the sizing is limited–however, I have a hack: most of the petite sizes are still in stock, so I would try ordering that! The petite sizing is only 2″ shorter–which I still think would be just as cute–especially because I often tuck mine in, so the length doesn’t really matter anyway! (And Nordstrom has free returns, so it’s worth a shot!)

Before we jump in, let’s go over the staples I used to create these looks.

Convertible sweater: First up, obviously. This sweater, you guys, is probably one of the most versatile things you could buy this entire year. It’s both cowl neck and off the shoulder. You can wear it as a tunic or tuck it into high-waisted jeans, skirt, or even over a dress!

I’m only showing you four ways to wear it today, but there really are ENDLESS ways you can style it and to top it off, it just might be one of the softest things I’ve ever purchased. (Oh, it comes in lot’s of colors too!) It’s so soft that this was the FIRST thing I put on when I transitioned my closet over to fall because I couldn’t wait to get it on my body ?

I typically tuck it in because I think it’s most flattering to show your waistline, but you can leave it tucked out as well. It’s more of a tunic length, shorter in the front than the back. I would highly recommend sizing down because it runs pretty oversized. For length reference, I’m 5’6.

Skinny Jeans: These haven’t been in stock in FOREVER! You guys know I have become obsessed with AE and Abercrombie who make some of my favorite (super budget friendly jeans) but there are some jeans that cannot be replicated and are worth the splurge, and these Rag & Bone skinnies are that. They were my #1 bestseller when I got them at the Nordstrom sale two years ago and they were sold out for so long–I always got asked to link similar and the thing is–there aren’t similar. They’re the real deal!

They are super stretchy, they feel like butter and unlike any other jean–they’re also not particularly thick which is why I think they’re so comfortable. I also love that the raw hem is very subtle–and the leg opening isn’t TOO skinny or too straight. They are ankle length. Sizing: I would say if you’re on the fence go with the size down because they are very stretchy–they run a bit big.

Heeled Booties: I recommend a pair of neutral booties for every fall wardrobe. If you go with one with a bit of a pointed toe, light tan color, and little bit of a heel, they also help to elongate your leg, which is hard to find in a bootie, as most of the time they can cut you off at the ankles and make your legs look stubby! A midi heel is great because it gives you a bit of height but is still comfortable for lot’s of walking!

The pair I’m wearing here is from last year, but I’d recommend this pair of Sam Edelmans if you want a bit of a heel or if you want a lower heel, this pair–which are insanely comfy! (Kelly has them in like 4 colors, haha!)  I’ve also been dying to try Everlane’s Day Boots–I’m in love with their Day Heels (they are SO comfortable) and I think the brown leather version is calling my name!

Leopard loafers: You’ve seen a LOT of these leopard loafers on this blog, because they really do make every outfit look instantly more stylish. Leopard always adds a ton of visual interest to any outfit. Plus, they are truly the most comfortable shoes I have ever put on my feet. They required zero break-in, no blisters–ever!

Leather tote: The Madewell Transport tote making the capsule wardrobe cut comes as a shock to absolutely none of you, I am sure. It’s my everything bag. Work, travel, groceries–whatever, this is always the bag I’m reaching for and it comes in several styles and colors as well.

Black pumps: I’ve owned this particular pair of Sam Edelman pumps for years but they make a ton of similar versions currently that you can shop here! They run TTS in my experience!

Trench coat: FULLY RESTOCKED! HUZZAH! It was gone for so long and now it’s back in ALL sizes! (Also in black!)

I purchased this trench by London Fog last Spring before my trip to London and it is one of my very favorite coats for both Fall and Spring. It has a detachable hood as well as a removable liner. Which unlike a lot of trench coats, does add a significant amount of warmth. I absolutely adore it and it’s one of my favorite jackets. It looks super chic for work, and just as pretty for dinner or a stroll around the neighborhood. It’s amazing for travel as well. Runs large, so size down. I’m wearing XS.

Leather jacket: I now own two leather jackets–one brown and one black. The black one is my newest addition and I don’t know what took me so long to get one! I definitely love both colors and I think whichever color is best for you just depends on your preferences. The one I feature here is also from last year but there are tons at really good prices here!  My favorite is this one, which is most similar to the one you see me wearing here!

Leopard clutch: For the same reasons as I sing the praises of the leopard loafer, I love a good leopard clutch! (Nordstrom actually has a TON of different leopard clutches right now!) I’m a huge fan of it for going out because it brightens up even the most basic outfit. Plus, it’s such a steal for less than $50 and it looks and feels like the designer version.

Belts: My gold buckle belt is Topshop and has since sold out (boo!) but this one is really similar and so is this one!

Okay, now let’s get into these looks!

Capsule Wardrobe Remix: The Convertible Sweater, Four Ways:

Look #1: Date Night

How to Wear the Convertible Sweater Four Ways by Jess Keys

Look #1: Date Night

Look #1: Date Night

This is a look that is suitable for just about anywhere in Chicago. Dinner, drinks, it’s great for all of the above! Throw a leather jacket over your shoulders and you’re good to go! (With the leather jacket I felt like I was subtly channeling a 2017 Olivia Newton John and I am so into it.)

Now, remember, this sweater is tunic length, which means you can wear it tucked in or out. I tend to prefer all of my shirts tucked in just because it defines your waistline and elongates the leg. Additionally, I think it makes it a bit more formal (for instances such as date night!) The pumps go a long way in dressing this outfit up, but not too much. I like them here because they’re a bit more feminine and “date” esque than if you were to pair this outfit with booties, but booties would work perfectly too!

You can see this demonstrated in the video above, but to tuck in, just take a corner of the sweater, twist it, and then tuck it in. It’s really easy!

Look #2: On the Airplane

Look #2: On the Airplane Animal Print Look #2: On the Airplane Look #2: On the Airplane

When you find a sweater that feels like a hug mixed with the softest blanket you’ve ever felt, it becomes a no-brainer to wear for travel. (Specifically I am referring to a fleecy, microfiber-ish, faux fur-ish blanket I found at Target last year that is wrapped around me as I write this post and will probably not be removed from my body until next April–unless it’s to put on this sweater). I know you have one of those blankets too. THAT is what this sweater feels like!

Anyway, pair it with your favorite jeans and the comfiest loafers ever (that slip-off quality comes in reaaallyy handy at airport security) and you’ll be good to go!

P.S. My suitcase is on sale right now on Amazon for $180! It’s one of my favorite purchases ever! You can see a full review of it here!

Look #3: Business Casual

Look #3: Business Casual Look #3: Business Casual Look #3: Business Casual

When you’re trying to get the most out of your wardrobe, it’s important to remember that you can layer OVER as well as under! This sweater is great layered over a work-appropriate dress! If you’re feeling a little “garbage baggish” like you have no shape, reach for a belt (mine is old but this one is similar!) and cinch it at your waist and VOILA. WOMANLY FIGURE! This look would also be just as cute with a pencil skirt or a pair of slim trousers or ponte leggings for an office-friendly look.

Look #4: Sunday Dinner Casual

Look #4: Sunday Dinner Casual

Look #4: Sunday Dinner Casual Look #4: Sunday Dinner Casual

Perhaps the best match of all for this perfect sweater is your favorite jeans, a pair of booties, and a plaid scarf (mine is last year’s but similar here at Nordstrom Rack!) . All you need is a PSL ;-P (By the way, if you’re looking for how to wear a scarf a few different ways, that post is right over here!) This is the perfect outfit for dinner or a movie to wind down the weekend!

How would you style the convertible sweater? 

Make sure not to miss our previous posts in the Capsule Wardrobe Remix series: How to wear a black dress four ways, how to style leather leggings 3 ways, and how to pack a carry-on travel capsule wardrobe!