Fall/Winter Fashion
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15 Valentine’s Day Outfit Ideas

What are your plans for Valentine’s Day this year? Are you doing anything fun? We usually go out to eat, but not on the 14th. We haven’t had much luck dining out on Valentine’s Day, but we usually celebrate sometime that weekend. I also love the idea of celebrating friends with a Galentine’s party.

Whether you acknowledge this Hallmark Holiday with a fancy dinner out, dinner at home, or something in between, I’ve rounded up some festive looks for your Valentine’s outfit inspiration.

15 Valentine’s Day Outfit Ideas

#1. If your plans are on the more casual side, you can’t go wrong with jeans and a cute sweater. It may be overdone this time of year, but I love to wear pink or red… or a combination of both! This LOFT Striped Shoulder Button Sweater is a perfect example.

I styled it with ribbed jeans and booties for a casual lunch look, or maybe you’re volunteering in your kid’s classroom at school. I miss those days!

LOFT Striped Shoulder Button Sweater (S) // Good American Good Legs Stovepipe (6; option) // Marc Fisher Alva Booties (8) // Kendra Scott earrings // Yurman bracelet // similar tote

#2. I also styled this sweater with grey jeans and the same light neutral boots, and I topped it off with my J.Crew Cocoon Coat.

LOFT Striped Shoulder Button Sweater (S) // Mother Hustlers (28; option) // Marc Fisher Alva Booties (8) // similar pearl earrings (11mm) // J.Crew Cocoon Coat (6)

#3. Take it up a notch or two for a dinner out with friends or your significant other with this monochromatic look and a pop of red.

grey cashmere crew (S) // AG Farrah raw hem ankle skinnies (28; option) // Sam Edelman Sulema Boots (8.5) // KUT from the Kloth Quinn Faux Suede Moto (S; option) // similar crossbody (more options)

#4. Here’s an outfit I put together a few years ago that I would still wear today, if I had kept this moto jacket. I’m not finding a lot that look just like it, but this light pink version is pretty, and BB Dakota has this one. I also like this burgundy option.

similar moto here and here; burgundy option // coated denim // Halogen tank // Marc Fisher pumps // Lucky Brand necklaceearrings

#5. This look is from last fall, but this sweater is a nice option for casual Valentine’s Day festivities. I think a few of you purchased this during last year’s #NSale.

AllSaints Ridley Funnel Neck Sweater in Pale Pink (S) // similar jeans (6) // Blondo Dagger Boots (size up half) // socks // earrings // crossbody (similar for less) // sunnies

#6. Dress up your favorite dark jeans with a burgundy blouse and gold accessories, like I did here for this holiday look. This would work for Valentine’s Day too.

Cece Tie Sleeve Top in Claret Red (S) // AG Mari straight ankle jeans (28) // Sam Edelman Hazel Pumps in Jute (8) // similar gold clutch // Stella & Dot earrings // similar layer necklace

#7. I also wore this top with black pants and black suede pumps to the Nutcracker last month. Again, so many holiday looks can work for Valentine’s Day.

Cece Tie Sleeve Top in Claret Red (S) // Vince crop leggings (M) // Marc Fisher pumps (8) // similar John Hardy hoops // Kendra Scott Satellite Elisa Pendant & Elisa Open Oval Necklace // similar shoulder bag

#8. Here’s a monochromatic take on that same look. The grey v-neck sweater and black pants pairing is luxe but understated, but the faux fur jacket and burgundy suede pumps take it up a notch. I also added blingy earrings to draw the eye up towards my face.

Vince Weekend V-Neck (S; budget option) // Vince Crop Leggings (M; option for less/budget option) // Sam Edelman Hazel Pumps in Boredaux c/o (8; also at Nordstrom) // faux fur jacket (sold out; option) // crystal drop earrings (option) // bezel station necklace // link bracelet

#9. I like how a light pink sweater gives a nod to the holiday without being too predictable, and this one is on sale right now! Also, these Mother Dazzler jeans just got restocked. I sized up to a 29 in these. This ultra casual look is great for anytime, but I especially like this color palette around Valentine’s Day.

Bailey Pointelle Pullover c/o Evereve (S) // Mother Dazzler Ankle Fray (29) // P448 Jack in Zebby c/o Evereve (39; also at Nordstrom) // similar pearl earrings (11mm)

#10. This cozy red sweater is still in stock, and it pairs well with black denim for a Valentine’s dinner out.

Halogen sweater (S) // wool coat (4) // Mother denim (28) // pumps (8) // necklace // similar earrings // sunnies (option)

#11. And here’s a burgundy and black outfit that’s a little more edgy and fun. This cozy v-neck is on a deep discount at Evereve.

Roan + Ryan Haley V-Neck c/o (S) // Spanx Leather Like Skinny c/o (M) // Sam Edelman Hazel Pumps in Jute (8) // Kendra Scott Satellite Elisa Pendant & Elisa Open Oval Necklace // similar beaded statement earrings

#12. Speaking of on sale at Evereve, this sweater and these pumps are included as well. I showed this outfit as an idea for New Year’s Eve, but it’s also a nice combo for Valentine’s Day.

Millie Shaker Pullover c/o (S) // Hudson denim c/o (28) // Sam Edelman Hazel Pumps in Boredaux c/o (8; also at Nordstrom) // clutch // earrings

#13. Apologies for the grainy picture; I think my camera was dirty, but I love this for a dressier occasion. Any grey or black sweater dress would work. Top it off with a red coat for an elegant dinner out look that’s perfect for any winter holiday.

tentree sweater dress (M) // Wolford black tights (M) // Sam Edelman Sulema Boots (8.5) // similar red coat // Kendra Scott split hoop earrings

#14. This sweater dress outfit is also an option. This LOFT cable turtleneck sweater dress is an extra 60% off with code XOXO, and it’s fully stocked.

LOFT cable turtleneck sweater dress (S) // Spanx tights (M) // Sam Edelman Sulema Boots (8.5) // similar shoulder bag // Kendra Scott earrings

#15. And of course, you don’t have to wear red or pink for Valentine’s Day. This blouse is still available, and it’s such a pretty print. Paired with luxe black pants and quilted slides or pumps, this makes an elegant look for a fancy dinner out.

Sanctuary Meadow Blouse (S) // Vince Crop Leggings (M; option for less/budget option) // quilted slides (8; or pumps)// open oval necklace // satellite pendant necklace // similar beaded earrings // similar clutch

Top it off with a faux fur jacket or a classic wool blend coat to complete the look.

Bernardo faux fur jacket (S; option)

I hope this roundup of Valentine’s Day outfit ideas was helpful. Even if you’re a bit of a Scrooge when it comes to Hallmark Holidays (who, me???) these outfits might inspire some of your late winter wardrobe planning for whatever you have coming up!

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27 thoughts on “15 Valentine’s Day Outfit Ideas

  1. The new font works for me. Random question, do you think TB Miller sandals are a classic? Are they going to still look current this summer?

    1. I definitely think they are on the downward slope of the trend spectrum, and not sure if they will be seen as a classic or not. I am afraid probably not but I will definitely wear mine this year. Not sure I’d advise buying a new pair tho.

      1. Thanks for getting back! I think I will hold off and see what you are showing in Spring and summer for sandals. Love your blog❤️

  2. Like the font change too! Thanks for the inspiration. My bday is the 13th so we always go out – a 2 for 1. Sadly, we used to go to NYC for this holiday and can’t wait to get back🙂

  3. Oh, I’m so glad someone mentioned the font. I had planned to and forgot to mention it on my survey. It was a little too small before and now its perfect. Great Valentine outfit ideas. We usually just stay in these days. Especially if it falls on a weeknight. I haven’t even looked to see when it falls this year. I’ve been thinking of Caroline when I see the snow storms in the East around Boston. How is she doing? We are having beautiful, sunny days in Oregon, but cool. Its been freezing at nights. I think the rain is back Sunday.

      1. She’s soooo cute. I think its neat how she is the baker. I’m sure her friends love it. Sounds like she settled in so quick with friends etc. I’m sure you are so thankful.

  4. I like the font change. And I laughed at your Scrooge comment…because that’s me! Loved the outfits though, especially the pink sweater with lighter-wash jeans.

  5. The font is great! I can almost read without my glasses lol! Last year we ate out with two couples and back to our place for dessert which was really nice, Not sure what this valentines will look like! Maybe just take out at home! It’s usually so cold too that we don’t feel like going out!
    Speaking of cold it’s frigid today and another snow storm on the way! You should definitely get your snow you’ve been waiting for this time around 🤷‍♀️

  6. Wow, that’s a lot of outfits! I like #10, I was looking for that Halogen red sweater!!! I also love your red coat. I have one red parka that I wear to death between Christmas and V-/day! Also, the font for the email is a LOT better now. Thanks for enlarging that!

  7. Thanks for the ideas! I have a question about the Millie shaker pullover from Evereve. Is the light oatmeal color more white or yellow in undertone. I can’t wear the yellow undertones but I like the sweater.

  8. I like the outfit ideas and I’m sure will be putting them to good use this year. I sure love those Mother Dazzlers but not the price point. Hopefully Bloomies will have a good sale like they did last year in March and I bought both of my Insider step hem pairs. BTW, Valentine’s Day is on a Monday this year. My husband and I wanted to go out to dinner but Monday is hard for us with work and kid stuff, so we decided to do it on Sunday. It turns out that’s Super Bowl Sunday! It seems very late this year, but we decided we didn’t care about the SB anyway and will just catch the end of it!

  9. Wouldn’t it look cute to “dress down” outfit number 14 by adding a leather moto jacket(?)! I LOVE sweater dresses in Winter for work and holiday gatherings….buuuttt: a black moto jacket with that combination would make it go from boringly formal to spicy date night casual, lol, immediately (AND: look a lot more realistically chic vs. worrying over those very self-conscious faux leather Spanx!).

    1. I think it has to work for your personal style, and you have to style it in a modern way or it can look frumpy real fast. I did style this one, and I actually meant to include it here. A friend of mine has it and she looked really cute in it. I haven’t worn mine besides this photo shoot, and I probably won’t. I’d rather wear something more sophisticated/edgy, but it’s fun on the right person. I do like how I styled it with the grey jeans and white boots: https://jolynneshane.com/snapshot/all-hearts-for-valentines-day

  10. Hi Jo-Lynne, are you seeing any more ivory/white booties coming out for spring? Seems most sold out so fast this year (esp if under $200),

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