Fall/Winter Fashion
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Valentine’s Date Night Outfit Inspiration

Okay, don’t faint, but I actually have an outfit today! I know, it’s been a while. But after back to back fall and winter outfit series and the hustle and bustle of the holidays, I was really feeling burned out. I’m starting to get back in the saddle, so to speak, and today I’m excited to share a Valentine’s Date Night Outfit with you!

To make it even better, I’m teaming up with Deborah from Fabulous After 40, so that’s TWO Valentine’s date night outfits for your fashion inspiration. AND, we will be back tomorrow with two Galentine’s party outfit ideas for you. No matter what you have planned for Valentine’s Day this year, hopefully one of our ideas will inspire you.

On the heels of yesterday’s post on 3 tricks for creating more interesting outfits, I have to admit, I’m feeling a little extra pressure today!

I didn’t really go shopping for this look; instead, I did what I normally do for our Valentine’s Day date nights — I shopped my closet!

Our Valentine’s date night plans usually consist of going out for dinner on one of the weekends preceding or following everyone’s favorite Hallmark holiday. Paul and I both love good food and good drinks, so we often pick a restaurant that is a little fancier than our usual, but we usually stay out here in the ‘burbs where nothing is super dressy.

It’s also important to note that here in Philly, February is usually one of the coldest months of the year, so when putting together my Valentine’s date night outfit, I usually go right for a pair of my favorite jeans and a cozy sweater. Then I add layers for interest and warmth.

That said, the day we shot this look, it was unseasonably warm, so I didn’t bundle up quite as much as I usually do, but I did choose over-the-knee boots because that’s usually my go-to for date nights this time of year. Besides looking super chic, they’re also the warmest footwear option in my closet.

If it’s cold when I wear this outfit next weekend, I may swap out my v-neck sweater for a turtleneck, and I’ll add my leopard-print wool scarf to the mix, but otherwise, this is pretty much what I’ll wear for our Valentine’s date night — cashmere sweater, dark wash skinny jeans, black suede over-the-knee boots, my trusty black leather jacket.

I added a red bag to make the monochromatic outfit pop, and of course the red is a nod to Valentine’s Day!

Yesterday we talked about 3 keys to an interesting outfit — focal point, juxtaposition, and a completer piece, and this outfit has all three. Not every outfit has to have all three to be complete, but I do find that my favorite outfits are the ones that incorporate them all.

This gorgeous red bag is the perfect pop of color against the monochromatic outfit, and it has both luxe and edgy components — but the juxtaposition can be found elsewhere in the outfit. I consider this bag the focal point because of the bold color and interesting chain-link accents.

The leather jacket is definitely the completer piece, and the  juxtaposition is here too — the tough leather jacket, the luxe cashmere sweater, the casual jeans (although they’re a dark wash, so not quite casual, but still…) and the edgy OTK boots create a mix of textures and styles that create some tension and contradiction in the monochromatic look.

Of course we never want to overlook fit and proportion when creating an outfit. Having a good collection of wardrobe basics that fit well is key to being able to shop your closet and put together different looks.

These dark wash jeans, black v-neck sweater, leather jacket, and OTK boots are all quality basics I’ve had for a couple of years and use over and over again to create different looks.

The bag is a newer addition — a bit of a splurge, but exactly what I’ve been looking for, and at half-off, I couldn’t resist. It’s luxe and edgy, a little different from what everyone else is carrying, and I have nothing like it in my closet.

Here are some more options for red clutches and crossbody bags at different price points:

I also added a couple of key accessories to complete the look. These Kendra Scott earrings were a Nordstrom Anniversary Sale purchase, and I’ve worn them a ton since I purchased them in July.

They make a statement without overpowering the outfit or the other delicate jewelry I may be wearing, and the unusual shape and filigree details are eye-catching. They’re not too much for everyday, but they’re blingy enough to carry off a date night look.

This bezel stone station necklace is a nice compliment to so many of my earrings. It’s delicate enough to support a statement earring, but it still adds a little something to an open neckline of this sweater..

Even though it’s small in scale, it has a lot of sparkle and shine, so I usually wear it with my dressier outfits.

There are a lot of options to tweak this look — it’s more of a formula than an outfit.

If your personal style isn’t as edgy as mine, you could totally swap out the leather jacket for a blazer; it would be classy and elegant and still have juxtaposition, a focal point, and a completer piece.

You could wear dark wash bootcut jeans and pumps instead of skinnies and OTK boots, or you could wear this outfit as-is and just swap out the OTK boots for pumps, which I may do if it’s not too cold next weekend — leopard pumps would be amazing with this look. Basically, whether it’s a scarf or pumps, I’m going to find a way to incorporate some leopard print!

There are so many options, but hopefully this look inspires you to shop your closet for whatever Valentine’s festivities you have planned!

similar jacket // sweater (similar here) // exact jeans // OTK boot options // red crossbody // earrings // necklace // photo credit: Alison Cornell

Shop the Post:

Be sure to visit Deborah to see the Valentine’s date night look she styled today; and as irony would have it, Cyndi has styled a Valentine’s date night look today as well, so be sure to check that out!

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22 thoughts on “Valentine’s Date Night Outfit Inspiration

  1. Another hit out of the ball park post. I appreciate the fact that you shopped your closet and explained why this outfit works. It fits you perfectly and is your style. Ohhhh…that purse. Having such a bag in a persons closet would be great- a bag that will last for years. 
    I need to add that I love your classic edgy valentines look. 

  2. Cute outfit and I love the pop of color from the crossbody. But I won’t buy MK purses anymore because they are everywhere but this one is def different and looks great on you. 

    1. I know what you mean. Unfortunately his MICHAEL Michael Kors line that is what is sold at most department stores has cheapened his brand, which is a shame because the original Michael Kors line is really lovely, and this luxury line — Michael Kors Collection — is stunning. I didn’t even know he had a luxury line until I wandered into his store at the mall a few weeks ago.

      I was there looking for a red crossbody, and I wanted something a little different from the other bags I have, so I started going into some other stores after I didn’t find much at my usual dept stores. I saw this bag sitting alone on a shelf and I made a beeline for it. The second I saw it up close, I knew it was exactly what I was looking for, and the sale price sealed the deal. I didn’t even take out the stuffing or try my stuff in it or anything. I was just like, “I’ll take it!” Very unlike me. ☺️

  3. I am really enjoying your explanations about juxtaposition. It’ll take practice and trial and error, but I think I’m going to be able to put this info to good use. Love the handbag–the first thing I noticed was the contrast between the heavy chain and luxe leather/shape–it really does look very cool, as does the whole outfit. Thank you!!!

  4. Thanks for shopping your closet. Terrific outfit!
    Enjoy the reprieve from Old Man Winter. The polar vortex is lingering on here: -13F or -25C 😖😝 Ugh…… Hope this means a milder spring!!

  5. Love the red handbag! It’s the best part of the outfit. For date night, heels would look nicer. The “look” of over the knee boots have never appealed to me. I hear chunky statement jewelry is on the way back in again.

    1. We’ll have to agree to disagree on that one. I love these boots with this look. But pumps would also look great — to each her own! 🙂 Yes, chunky jewelry and statement necklaces seem to be making a comeback this season, but as usual, they’ve changed it up a bit so it doesn’t look like the statement necklaces of 2009. I do think a chunkier necklace could really enhance this look — or multiple layered necklaces. I didn’t have anything quite right in silver, and I had to stick with silver b/c of the bag.

      Which is a really good lesson in outfit creation, actually. Jewelry really shouldn’t be an afterthought — and I admit, it usually is for me. I mean, I went shopping for a bag for this look, but I never thought to pick up a necklace that would go too, and if I’d thought about it, I’d have known I didn’t have anything quite right. Anyway… I digress! 🙂

  6. Thanks for recapping the 3 rules from yesterday in this post. I loved the reminders as I train my eye to watch for these items when I put my outfits together — I hope you’ll continue to incorporate these ideas. I can lean to frumpy and your simple tips help a lot. BTW I bought your black leather jacket last year because I thought it was so cute and it’s become a favorite staple in my closet. Thank you!

  7. Boy I can’t wait  for it to warm up enough to wear my black leather jacket( that I got for Christmas). I keep trying but it’s still been too cold in the negative digits.  I love that little red handbag. It really does make the outfit…❤️❤️

  8. Do you have any suggestions for black sweaters that fit like these but are not dry clean only? I’ve ordered several and they end up being too long or too boxy. I like the form fitting shape like these. Looking for both V neck and cowl neck that aren’t a really loose weave. 

  9. Just to echo everyone else, I love this outfit and the bag is what really sets it apart—it is gorgeous!  I also just looked at your roundup of Valentines looks from last year and got a lot of great ideas. I only started following you around Easter last year. You have really helped me up my game, and my husband has noticed!  Thank you!

    1. Yeah, I have always religiously dry cleaned my sweaters, but I’m going to try it with one of my older ones… the thing I hate the most about doing it myself is finding places to lay them out to dry, lol.

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