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A cute casual outfit for Valentine's Day with a red linen shirt over tan trousers.  I added a chunky pearl choker and tan D'orsay pumps.

//Red blouse, pants, shoes, bag, necklace, watch, earrings, //

For all my Valentine’s Day lovers, in this post, I will show you six different casual outfits for Valentine’s Day. CLICK on the captions to see any of the links.

I love both red and pink and therefore had absolutely no trouble coming up with lots of different looks involving one or the other color. Here are some cute casual outfits for Valentine’s Day mostly with items that were already in my closet!

In this post...

Cute Casual Outfits for Valentine’s Day: Outfit #1

This first look could easily go to the office or out to lunch with friends. It’s a red shirt (old) worn untucked over a J. Jill pair of tan essential cotton khakis. (If it’s cold for you, add a tan camel hair coat or a pretty black wool one.

The narrow uncuffed leg is more dressy than the usual, more slouchy ones associated with the term chinos. Notice how I rolled the sleeves a bit which allowed a more casual, but still classy look.

My Talbot’s multi-stranded pearl choker is such a crowd-pleaser. It’s old but I’ve linked a similar solution under the photos. Pro Tip: The choker I linked below is two necklaces and I would suggest purchasing two so that you will end up with four strands as in my look below. Or you could just mix several strands of pearls from your collection.

A cute casual outfit for Valentine's Day with a red linen shirt over tan trousers.  I added a chunky pearl choker and tan D'orsay pumps.

//Red blouse, pants, shoes, bag, necklace, watch, earrings, //

My tan doctor’s bag is by Coach (similar, above in photos) and my blush patent leather block-heeled D’orsay pumps are by AGL (similar, above in photos).

Cute Casual Outfits for Valentine’s Day: Outfit #2

Another cute casual Valentine's Day look with a heart-themed shirt, distressed jeans, a pink cross-body bag.

//Pajama top (similar), jeans, cross-body, sunglasses, earrings, watch, sneakers, wreath (similar)//

Another cute casual Valentine's Day look with a heart-themed shirt, distressed jeans, a pink cross-body bag.

//Pajama top (similar), jeans, cross-body, sunglasses, earrings, watch, sneakers, wreath (similar)//

Fun white gym shoes with pink soles and trim.

//similar pink sneakers//

The second look is a fun weekend errand look. It’s a heart-themed Loft pajama top (similar, here) worn over vintage Kut from the Kloth distressed jeans. I LOVE the idea of wearing a pajama top out of the house. So fun! So unexpected!

My crossbody pink purse was a perfect accessory (color is begonia) while my absolute favorite item is my pink-soled Cole Haan sneakers that I found recently on sale at Saks Off Fifth online (similar pink sneakers are linked in the photos. Aren’t they so sweet?

Cute Casual Outfits for Valentine’s Day: Outfit #3

Casual Outfits for Valentine's Day

// Similar red vest, turtleneck, skinny jeans, booties, bag, earrings, watch, sunglasses, tulip wreath//

This third look combines my love of red with black and white stripes. I’m wearing a black and white striped cotton J. Crew turtleneck under a Brooks Brothers red vest (that I got on sale for 50 % off!) (similar vest linked in photos). My jeans are Old Navy’s dark wash Rockstar super skinny jeans which given their name are remarkably comfortable and at a terrific price.

My tan booties are comfy suede, my black bag is Coach and my sunglasses are Oakley’s. Again if it’s not too cold where you live, pushing up your sleeves allows you to show off your jewelry and looks more interesting than leaving them down. Again, if it’s cold for you, add a winter wool coat over this look.

Cute Casual Outfits for Valentine’s Day: Outfit #4

Another casual outfit for Valentine's Day with a black sleeveless top and black knit trousers.  I then added a red and white flowy ruana and a black with red roses little bag.

//Similar purse, similar red ruana, similar Vince black top, pants, similar black suede shoes, earrings, watch, bracelet, similar wreath//

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This next look is what I’m wearing to dinner this weekend. This red print ruana is a great topper for my black v-neck Vince silky tank top and drapey black knit J. Jill pants. The combination reminds me of silk pajamas. Of course, if it’s colder where you are, change to a black turtleneck, and maybe, black booties with a classic black overcoat as the top layer.

My shoes are black suede D’orsay AGL pumps with a block heel (easy to walk on) and have an ankle strap. My favorite part of this look is my tiny red rosebud-covered evening bag by Julia Feldman. It’s honestly many years old and I think I found it in a consignment store. I linked a red clutch under the photo that would work as well. Lastly, notice the classic jewelry of my trusty Ebel watch, a pearl bracelet, a diamond bangle, and pearl stud earrings.

Cute Casual Outfits for Valentine’s Day: Outfit #5

A pink cashmere tunic with black leggings for a fourth of six cute casual outfits for Valentine's Day!

//Scarf, similar pink sweater, leggings, similar bag, booties, belt, wreath, watch, earrings//

This pink cashmere tunic is from Sara Campbell (similar, linked in photo). I added an old pink leopard scarf (similar one in the photo) as well as an even older black suede belt (similar one in the photo). The leggings are my favorite (I have four pairs of these) black Lysse Pointe leggings. The booties are black suede and my black bag is from Coach.

Shop My Looks on LTK!

Cute Casual Outfits for Valentine’s Day: Outfit #6

My last of the casual outfits for Valentine's Day look was with a red sweater over a blue dog print shirt.

//Leopard tote, leopard shoe, red sweater, similar shirt, tan pants, watch, earrings, wreath//

My last casual Valentine's Day look was with a red sweater over a blue dog print shirt.

//Leopard tote, leopard shoe, red sweater, similar shirt, tan pants, watch, earrings, wreath//

My last outfit is “going to the dogs”! It’s a great red cotton Ann Taylor turtleneck side buttoned sweater (similar, below) worn over a blue oxford cloth Talbots shirt (similar, below) with darling doggies and bones all over it! I wore the tails un-tucked with the cuffs rolled back over the edge of the sweater. My pants are the same J. Jill ones from the first look and my leopard slip-on shoes are so comfy. My leopard tote is so practical. I love using leopard as a neutral to add a fun detail to an ensemble.

So folks, there you have it. Six lovely Casual Outfits for Valentine’s Day looks for most occasions. Let me know in the comments below which one(s) you liked best. Also, check out these four ways to wear a cardigan.

ALSO PLEASE LET ME KNOW ANY FASHION QUESTIONS YOU WOULD LIKE ME TO ADDRESS IN A FUTURE BLOG. THANK YOU SO MUCH!!!

Happy Valentine’s Day!

Check Out These Items to Inspire Your Valentine’s Day:

Avara heart earrings
Avara pretty pink mules
Avara red top with white hearts
Avara pink (or red) heart bag
Avara blue top with pink hearts
Avara black Love top
Avara Hershey’s Kisses top
Avara white sneakers with white edge

XO

Dr. Julie

PS Here are a few more fun posts for you to enjoy!

Ina Garten’s Lemon Yogurt Cake

A Sweet Valentine’s Day Tablescape!

Ponchos, Wraps and Shawls

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