My Flirty Tomboy Alter Ego (& These Red Heels!)

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This post is sponsored by Saks Fifth Avenue.

I talk a lot here about my whole feigned effort take on dressing and how that’s translated into what I’ve been calling my Schleppy-Chic Style over the past couple of years.

What can I say — I like high-impact and low-effort outfits. (I mean, what’s not to love…?) Which is why this alter ego I turn to pretty much any time I want to get dressed for real works equally well.

I call her Flirty Tomboy, and she’s been with me since high school. She’s cool but not too cool. Obsessively collects lip gloss and changes her own oil. (Fun fact: I can!) And has all of three hairstyles in her arsenal: down, ponytail and messy bun (obv.).

Dressing Up A T-Shirt & Jeans (Yes, Again…): Flirty Tomboy Style

When it comes to dressing, the Flirty Tomboy formula is simple: jeans, T-shirt, something menswear-ish. Finished off with a few sweet details that make the whole thing feel more intentional, while still, of course, being easy as heck to wear.

I know, I know. Dressing up jeans and a tee? We’ve seen this before. But I’m not claiming to be breaking new ground here. Instead, consider this a reminder that it’s a classic for a reason.

When it comes to dressing, the Flirty Tomboy formula is simple: jeans, T-shirt, something menswear-ish.

blazer (XS, runs slightly large) | baseball tee (XS, TTS) | jeans (25, TTS) | heels (TTS) | clutch

This getup is my go-to for brunches, girls’ nights, and, especially, dates with Chris when I want to feel a little more like the gal he fell in love with. I mean, I am, of course, the same person. But as anyone with kids can understand, I’m also…so very much not. So, while Schleppy-Chic Em is cool and comfy and not trying-too-hard, Flirty Tomboy Em is trying just enough. *plays with hair* Giggle.

Being completely frank here, I also think Chris would agree that Flirty Tomboy Em’s style appeals more to his general taste in women’s fashion. And while I wholeheartedly believe you should dress for you, it feels good to catch the eye of your beloved every now and then.

Dress up a T-shirt & jeans for Valentine's Day...ft. my Flirty Tomboy alter ego. Just add a li'l menswear (a sweet blazer) & a pop of color (red pumps).
Dress up a T-shirt & jeans for Valentine's Day...ft. my Flirty Tomboy alter ego. Just add a li'l menswear (a sweet blazer) & a pop of color (red pumps).
Dress up a T-shirt & jeans for Valentine's Day...ft. my Flirty Tomboy alter ego. Just add a li'l menswear (a sweet blazer) & a pop of color (red pumps).

#SaksStyle — Flirty Outfit-Makers (That Aren’t Too Sweet)

So, this Valentine’s Day, this is what I’ll be wearing. It feels so unapologetically me that I’m smiling just writing this post. And it revolves around a couple of really fun outfit-makers that I’m so excited to have picked up from Saks recently.

As you know, we’re big fans of Saks Fifth Avenue around here. Just seeing that iconic Saks script on the website brings me back to my adolescence, when shopping Saks was almost unfathomably cool and, as such, an incredibly exciting, rare treat. (True story: my first-ever Saks purchase was a tube of copper Christian Dior hair mascara — anyone else!?) I still get those little butterflies shopping Saks today.

rMy Valentine's Day outfit revolves around a couple of fun outfit-makers that I'm so excited to have picked up from Saks recently.

blazer (XS, runs slightly large) | baseball tee (XS, TTS) | jeans (25, TTS) | heels (TTS) | clutch

Easy Valentine’s Day Outfit Inspo: Add An Iconic Menswear Blazer + A Pop Of Red

While I adore shopping Saks in store (it’s one of those things I reserve for me time — no kiddos allowed, thankyouverymuch…), shopping Saks online is intuitive and fun, and it’s one of the first places I turn when looking to add something investment-worthy to my wardrobe. Like the Anine Bing plaid blazer I’m wearing here. Or these red Kate Spade pumps that were the inspiration for this entire post. More on both of those, and everything else the Flirty Tomboy in me is loving, below.


This Anine Bing blazer is the kind of piece that pairs just as easily with a dress + heels as it does with wide-leg jeans, a sweater + chunky boots.

Anine Bing Diana Plaid Blazer: I’ve long been eyeing an Anine Bing blazer, and this one just felt right. (Anine Bing, after all, is the embodiment of Flirty Tomboy perfection.) The proportions of this blazer are both nostalgic and modern, the texture and plaid pattern classic. It’s the kind of piece that pairs just as easily with a dress and heels as it does with wide-leg jeans, a sweater and chunky boots. And, of course, it’s ideally suited to a jeans-and-T-shirt situation.

The quality is excellent too — as well it should be, for the price. But for a timeless piece that will see regular wear at least three seasons of the year around here (it’s a heavier weight, something between a suit jacket and a light coat), it feels like it’s worth the investment. For sizing, I’m usually between an XS and S, and I’m wearing the XS here, which is intentionally oversized but not laughably so.

Worth noting: I don’t typically wear my coats or blazers over my shoulders because of the seemingly awkward, impracticality of it all, but damn, if I won’t start now. In fact, I’m almost annoyed by how much I love the draped look (scroll up a photo or two), dang it. I’m blaming the blazer because it’s just that good.

That little bit of sparkle on the buckle makes the Kate Spade Mary Jane pumps feel just glam enough — & the cut is even a little bit sexy.

Kate Spade Marlene Mary Jane Pumps: These were the impetus for this entire outfit. I took one look at them, and it was lust at first sight. I immediately knew they’d refresh all my favorite jeans. Add in the fact that they remind me oh-so much of a pair of Kate Spade heels that I (regretfully) parted ways with years ago, and I was sold.

The color is happiness, distilled, and the perfect nod to Valentine’s Day (if a little on the nose). That little bit of sparkle on the buckle makes them feel just glam enough — and the cut of the shoe itself is even a little bit sexy. I mean, a Mary Jane is a classic for just about any occasion, but add in a wee bit of toe cleavage and it’s downright date-worthy.

And I don’t say this lightly, but they’re actually pretty dang comfy. Once upon a time, I used to be team nothing-shorter-than-4-inches, but the 3.25-inch heel on these is just right. There’s a slim bed of cushioning too. Fit is true to size.

This Veronica Beard baseball tee is the ultimate tomboy essential, & the puff sleeves on are a sweet detail that's not too frilly.

Veronica Beard Mason Baseball Tee: I can’t remember a time when I didn’t have a baseball tee in my closet. They’re the ultimate tomboy essential, and the puff sleeves on this one are a sweet detail that’s not too frilly. And while a slouchy baseball tee can have really cool, boyfriend-y vibes, the semi-fitted nature of this tee is such a welcome departure from all the oversized things I’ve been draping myself in lately. Cute, comfortable, and something I’ll absolutely reach for again and again. Wearing an XS.

Fit of Levi's Wedgie jeans is true to size & is ideal after a little break-in, but for a lower-maintenance fit, you could also size up.

Levi’s Wedgie High-Rise Straight-Leg JeansThese Levi’s Wedgie jeans are ideal if you’ve been unsure how to migrate away from skinnies — they’re still fitted and flattering on the bum, and the leg is straight enough to feel current while juuuust skimming curves where it counts. I’ve owned them for a few months now, and they’re the pair I reach for most when I want something that’s not wide-leg or too roomy through the seat and thigh.

I love the juxtaposition of the black denim with the bright heels, but these are only too good with white sneaks too. Fit is true to size and is absolutely ideal after a little break-in, but for a lower-maintenance fit, you could also size up.

This black clutch is deceivingly roomy inside, & the signature Loeffler Randall pleating makes this bag so elegant.

Loeffler Randall Rayne Pleated Clutch: This clutch is another piece I’ve been eyeing for a while knowing that most of my handbags — even the little ones — skew rather casual. It’s deceivingly roomy inside, and the signature Loeffler Randall pleating makes this piece so elegant. The gold chain strap is fully removable, so it can be worn on the shoulder or tucked under your arm, as well.


Get your flirt on, gang!
xo,
Em

Thank you to Saks for sponsoring this post. Saks has such lust-worthy pieces, and it always feels like a treat shopping there — whether it’s in person or online — so it’s extra-special to get to work together and sing its praises here. And thank you so much for reading and spending time with us here at The Mom Edit. We love doing what we do and are so appreciative of your support!

Friends! Follow me on Instagram for accessible, easily adaptable recipes; sneak peeks of The Mom Edit content (and sales!); and more snippets of our life on the Northern California coast. And if you feel so inclined, pop over to my personal food + lifestyle blog, The Pig & Quill, where I share salty scribblings from my kitchen and home life. Byeeeeee!

Photos by Carolyn Stockman. Thank you, friend! We always have too much fun. 🙂

And Pinners, this one is just for you!

Dress up a T-shirt & jeans for Valentine's Day...ft. my Flirty Tomboy alter ego. Just add a li'l menswear (a sweet blazer) & a pop of color (red pumps).

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