My favorite online boutique, Pink Lily, has released the CUTEST line of Valentine’s Day outfits and I could literally buy all of it! I’m sharing my top picks for both casual and dressy Valentine’s Day outfits, and what pieces have made it to my cart so far.

PLUS, use code JANUARY15 at any of my links below to get 15% off your entire order!

Casual Valentine’s Day Outfits

These tops can be dressed up or down for a perfectly casual look no matter what plans you have. They’re great picks for the residual 2020 energy we’re still feeling in early 2021 (a.k.a. co-zay all day).

Think I’m Falling For You Sweater

A cozy, chunky sweater with a classic big red heart on it. Literally, if you have a head on your shoulders you can pull this look off!

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Love Your Heart Sweater

The brighter the better. This cream sweater has pops of bright red heart outlines for the perfect balance of fun but classic. If you’re looking for even less ‘pop’ it also comes in a beautiful gray and white design.

Pink Heart Sweatshirt Valentine's Day Sweater

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Simply Sweet Distressed Heart Sweater

Comes in small through 2X for a comfortable fit for all. Plus, there’s also a white and pink sweater color option. This one is one of the items in my cart!

Red and Pink Hearts Sweater Valentine's Day

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Valentine’s Day Graphic Sweatshirts + Slippers

Beginning last V-Day, I haven’t been able to get enough of heart print sweaters. They were cute last year and this year they’ve leveled up. Pink Lily has a bunch in their VDay shop but these are my picks for the best of the best.

LOVER Block Graphic Sweatshirt

This one comes in sizes small through 3X, something I really love about Pink Lily overall. Their shirts and sweatshirts are all very size inclusive! No one wants to feel stuffed into this adorable LOVER sweatshirt, which comes in either hot pink or black.

LOVER Block Hot Pink Graphic Sweatshirt

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Heart Outline Graphic Sweatshirt

I just hit purchase on this today. How cute, right?! I’m imaging this with leggings, comfortable boots and a puffy vest when I’m out running errands. This sweatshirt will also work with jeans in a slightly more dressed up outfit.

Red Heart Outline Sweatshirt

I ordered Large for a TTS fit, following the size chart specifically considering the bust measurement and wanting the extra room for a cozy fit.

Pink Lily Heart Sweatshirt

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Kiss Me Lips Graphic Tee

Such a cute graphic tee! Comes in a few colors but I think the white one with the pink lips is by far the best one. This shirt runs from small through 3X, so also very size inclusive! Follow the chart for guidance when ordering.

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Taken Graphic Sweatshirt

Say it with your sweatshirt! And be comfortable while doing it. Going out to a casual eatery or staying home, this sweatshirt is a great option for both and comes in two colors.

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XOXO Graphic Sweatshirt

Simple and sweet, and very size inclusive. All great reasons to make this sweatshirt your choice for Valentine’s Day this year. Also comes in a gorgeous hot pink color!

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Babe Graphic Sweatshirt

Another gorgeous colored, comfortable sweatshirt on theme perfectly for Valentine’s Day. I adore the pink color of this one!

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Leopard Slippers

If you have cold floors like I do, these slippers are a must. I got them over the Christmas holiday and it was just in time as the Midwest cold really set in. Toss these in your cart when you order your Valentine’s Day outfits, you won’t regret it! Wearing size Large for TTS fit (I wear 9.5/10 in shoes). Not to mention, they match my On The Prowl Leopard Sherpa perfectly, too.

Leopard Print Sherpa Slippers Valentine's Day Outfits

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Valentine’s Day Slippers

These two pairs of slippers come in V-Day friendly colors that will carry through the entire year. These red slippers run similarly true to size, as do these pink ones that are exactly like my leopard ones, just in pink! Both come in multiple colors options.

SHOP RED SLIPPERS | SHOP PINK SLIPPERS

Dressy Valentine’s Day Outfit Inspo

Never Late To The Party Hot Pink Dress

This dress screams Valentine’s Day, and even better, it could also scream warm, tropical vacation or summer nights out. You could wear this for so many occasions beyond V-Day. It’s an all-around great pick for under $50!

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Soul Searching Smocked Blouse

Another year-round wearable piece that would be an adorable choice for Valentine’s Day. You can dress this shirt up or down easily and it’s work, brunch and drinks appropriate. I’m all for a versatile piece, if I’m spending the money the top needs to really work for me, and this one does!

Casual Valentine's Day Outfits

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Beautiful And Bold Tassel Earrings

If it’s got fringe, it’s probably got my approval. These tassel earrings go with virtually any of the outfits I picked out, so I had to share these with you. I’d wear these all summer and with any bold outfit after Valentine’s Day, too!

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Dream By Daylight Blush Romper

Throw your favorite piece of neck bling and pair of heels on and BOOM, you have the cutest Valentine’s Day outfit for a date night out! This romper comes in four gorgeous colors, but the blush pink romper has to be my favorite. They also recommend sizing up due to the fitted nature of the piece.

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Dancing On Main Street Earrings

These ivory wear-with-anything earrings are the perfect neutral balance to any brightly colored Valentine’s Day outfits. Looking for more vibrance? They also come in a very Valentine’s Day or Christmas holiday colored red.

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You Make My Heart Shine Red Dress

For the grand finale, I saved this little number. If you have a hot date this Valentine’s Day, you’re welcome. This dress is a closet staple and you can’t beat the color! Also comes in hot pink, but my top honors go to the red for the most romantic of holidays.

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Which one are you inclined to grab? Or perhaps there another item you found on their Valentine’s Day edit page? I’m having a hard time picking just a few. Help me break the ties in the comments!

More Fashion + Outfit Inspo

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Valentine's Day Outfits


This post contains referral/affiliate links. A small commission may be earned if products are purchased through my links. Thank you for supporting the brands that support this blog.