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Casual Outfits for Valentine's Day

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!

This first look was what I wore to a tea party. It’s a red J.Jill linen shirt worn untucked over a J.Jill pair of tan essential cotton khakis.

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 you could recreate the look by putting on several different pearl chokers simultaneously. My tan doctor’s bag is by Coach and my blush patent leather block heeled shoes are by AGL.

Casual Outfits for Valentine’s Day

The second look is a fun weekend errand look. Its a blue heart-themed Loft pajama top worn over vintage J.Crew distressed jeans. My crossbody pink purse was a fun accessory while my absolute favorite item is my pink soled Cole Haan sneakers that I found this week on sale at Saks Off Fifth on-line. Aren’t they so sweet?

Casual Outfits for Valentine's Day

This next 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 Brother’s red vest (that I got on sale for 50 % off!). My jeans are Old Navy’s dark wash Rockstar super skinny jeans which given their name are remarkably comfortable.

My booties are from Lands’ End, my black bag is Kate Spade 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.

Casual Outfits for Valentine's Day

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.

My shoes are black suede D’orsay AGL pumps with a block heel (easy to walk on) and has 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. Here is another cute red clutch that would work as well.

This pink cashmere tunic is from Sara Campbell. I added an old pink leopard scarf (here’s a similar one) as well as an even older black leather belt. The leggings are my favorite (I have four pairs of these) black Lysse pointe leggings. The booties are black suede Aquatalia and my black pebbled leather bag is from Kate Spade.

My last outfit is “going to the dogs”! It’s a great red cotton Ann Taylor turtleneck side buttoned sweater worn over a blue oxford cloth Talbots shirt that has 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-ons are from Sperry. My leopard tote is from Sole Society. 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.


Happy Valentine’s Day!


Dr. Julie

PS Some of my readers have asked me the significance of items that have been typed with pink ink.  These are “magical links” because when you click on them, you will be brought right to the site where you can purchase that item if you so choose.  They are officially called “affiliate links” which means when you shop through them, it helps support my blog (all at absolutely no additional cost to you) so thank you for using them!

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