Valentine’s Day Outfits – Dressy & Casual

If you read my How to Plan Your Entire Year in Advance post, you know I try to get ahead of the game and get things planned out in advance so I’m not losing my mind later.  I’m happy to report I did pencil in a Valentine’s Day date, but unfortunately, I haven’t been able to find a sitter yet! I haven’t given up hope yet though!

I know a lot of us don’t do much for V-day, but if you happen to have plans for a nice dinner date, I’ve pulled some looks for you that your man would love to see you in, I’m sure!  And you’ll feel ultra pretty because it’s fun to put on a sassy dress and get all fancy once in awhile. If that isn’t in the cards for you this time, I also styled an adorable casual red and white stripe top that would be very cute, perfect for a low-key dinner.


I always associate red and pink with Valentine’s Day, but it doesn’t have to be a lot of that color.  Even the little bit of red stripe in this top looks festive for the occasion.striped top and jeans with red heels

Stripe Top XS • High Waist Jeans 25 • HeelsNecklace • Customizable Bag • Watch • Bracelet • Sunglasses • Earrings

The adorable striped top is actually sweatshirt material, so you’ll feel weekend comfy, but it dresses up easily with heels and accessories!

I’m loving all the fun designers are having with sleeves lately! From cold shoulders (like the striped top in this post) to bell and flare sleeves, and here, a drop shoulder with a slight puff to them!

striped top and jeans with red heels

striped top and jeans with red heels

That small detail, along with the v-neck and length of the sleeves and crop shape makes this sweatshirt unique. I was worried that the crop top would be belly baring and we DON’T want that! But, especially with these high waist jeans, your tummy is safe from exposure! #thankyouverymuch!

striped top and jeans with red heels 2 (4)

striped top and jeans with red heels

Stripe Top XS • High Waist Jeans 25 • Shoes • Necklace • Customizable Bag • Watch • Bracelet • Sunglasses • Earrings

JEANS FIT TIP: These jeans are the ones you’ve heard me raving about since I got them. High waist jeans for the win! #twokids The high waist on these jeans isn’t SO high that it’s uncomfortable, but just high enough to hold you in and make you feel secure.  They have a good bit of stretch and a nice wash, fitting TTS, but you could probably size down if you’re in between sizes.  I ordered my regular size 25 and they fit fine- they are supposed to be crop, but on 5’1 me, they are all the way to my ankles. But I like to cuff mine at the ankle anyway.  And they’re under $65!

striped top and jeans with red heels

striped top and jeans with red heels

I showed you a vibrant and fun bag yesterday, and today it’s all about that print and leopard!  Mixing stripes and leopard is one of my favorite combos.

You can seriously lose yourself for hours on the Barrington website because you get to customize the bag!  First you choose which bag you want, then you can pick your print and add a center stripe in your favorite colors, and even a monogram if you want!

I finally narrowed mine down to the leopard print with a light tan trim (you get to choose that too!) and pink and red stripe with HWH as my monogram!

Barrington Bag leopard

And these are the same heels from yesterday’s Pop of Sunshine, just in a vibrant red!!  The heel is pretty high and stiletto, so they ain’t made for walkin!  But they are perfect dinner date shoes! 

Leopard bag and red heels

striped top and jeans with red heels

Add these pieces to your wardrobe by clicking the pictures below!


Red white stripe tunic and leggings (1)

Tunic Sweater Now $25 • Similar Vest Under $20 • Leggings • Boots 55% Off • Savannah Zippered Tote

Y’all LOVED this red and white stripe tunic sweater and if you didn’t get it yet, it’s on sale + an extra 50% off in all sizes!!  I paired it with leggings here, but it also looks great with jeans!


And for those of you that want to get a little dressed up for Valentine’s Day, that holiday is a perfect opportunity! It might not be too often that you put on a sassy LBD, but I know you will rock it and feel fabulous in it!

Dress XS • Clutch (Similar) • Shoes • Sunglasses • Similar Moto Jacket (size up) • Earrings • Bracelet

I tried on this black crochet number in my latest Dressing Room post and y’all loved it!  The crochet detail is stunning and very well done. The lace overlays the hem at the bottom and there’s a hint of some skin showing which is a nice touch for a romantic date night.

It’s actually quite comfortable and I wore a black strapless bra with it!

The back is super cute too!

Little Black Lace Dress 6

If it’s chilly wear you are, just throw on your faux leather jacket.  It was actually so cold while we were taking these pics, but I’d still definitely wear this dress out.  It’s only a short walk from the car into the restaurant!

Little Black Lace Dress Dress XS • Clutch (Similar) • Shoes • Sunglasses • Similar Moto Jacket (size up) • Earrings • Bracelet

Did you notice that grommet detail at the top? I like the edge it lends this dress, along with the artful detail that defines your waist.

Little Black Lace Dress with black aviators


Add these pieces to your wardrobe by clicking the pictures below!


Holiday Party Dress- lace dress #LBD #partydress #Fallfashion
I’m crazy for the detail on this dress and the lace pattern goes in a chevron pattern.  They keyhole neck opens it up, but it isn’t too revealing.
Little Black Dress #lbd #littleblackdress #partydress 2
And it looks as good coming as it does going. You can wear this backless bra for some lift and coverage while keeping your back bare. It’s recommended to order one size up, but for me, my normal size is what fit best.
Little Black Dress #lbd #littleblackdress #partydress 4

Ruffle Dress XS • Clutch • Earrings • Similar Leopard Heels • Red Lips “brave red”

This long sleeve dress is a good option if you tend to get chilly in restaurants, but still want to wear a dress. It’s flirty and feminine and a bit sexy with the plunging neckline.  You could add a lacy bralette underneath or a lace trim camisole if you prefer to be more covered up.  I feel like the longer sleeves helped me feel like not too much skin was showing.  It fits TTS, and is super flattering.

Little Black Dress Under $50 #lbd #littleblackdress #partydress

Ruffle Dress XS • Clutch • Earrings • Similar Leopard Heels • Red Lips “brave red”

 If you happen to have bought that easy going shirt-dress in ANY color(it’s available in NINE), you can definitely make that work for a dressy Valentine’s Day by adding heels and accessories!  See how I’ve styled it several ways here and here!

Magic Dress

Black Dress XS • Poncho • Boots • Tassel Necklace

This “magic” dress has the perfect amount of ruching to be flattering on every body type – I even wore it pregnant! ?   It comes in a ton of colors and also sleeveless. The Poncho is a great layering piece and won’t overwhelm a petite frame.

If you want even more LBD options, check out this post with 9 gorgeous black dresses under $100!

Valentine's Day Dressy & Casual

Will you be dressing up or down for Valentine’s Day??


NORDSTROM • Great sales happening right now! The Must-Have Tunic is on sale in ALL the pretty soft colors and this ruffle hem top are both under 33% Off!

LOFT • 40% Off Everything – 50% with a LOFT card – 60% Off Winter Faves!! Check out this sweater in perfect pink.

ANTHROPOLOGIE • This fleece pullover has the cutest ruffle detail!!

EXPRESS • 50% Off Clearance! Check out the cute sleeves on this sweater!

GAP • 50% off almost everything and 20% off your entire purchase! I’m loving the look of this midi skirt!!

JCREW • EXTRA 50% Off Final-Sale Items! This short sleeve dress would be a perfect option for Valentine’s Day too!

OLD NAVY • 30% off one item you love and 20% off your order! Check out this $15 shirtdress!

Have a great weekend friends! Hope to see you back here next week!!

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Meet Megan

Hi! I’m Megan, mom to a thoughtful teenager and spunky young girl. We call Houston home and recently moved into our dream home. I traded my lawyer hat to become a full-time blogger in 2010. I love sharing my passion for affordable fashion, home decor, organization, & fitness to help inspire you to take care of you!


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