How To Wear Plaid Part 4 – With High-Waisted Denim

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-1 For moms without a post-partum pooch (like M above, lucky girl)…plaid shirts get a sophisticated twist when tucked.

M tucked her cheap-n-easy Target plaid shirt into a pair of higher-waisted flare jeans, added a cool belt, necklace and heels.

I'm loving the choice of a girly necklace/belt with the plaid.  And who doesn't love red shoes?

Now, I know we tend to focus on mom-friendlier footwear than M's sexy red heels…but I've gotta be honest.  I've been struggling a bit with the flares + flats combo. I'm planning to play around with it (and let you know the results, even if it's a disaster)…but if any of you are successfully rockin' the flare/flat combo, please let us know.  Warning:  We will harass you for a pic.

Anyway.  I do love M in this outfit.  So classy, yet comfy.  Nice.

If, however, you are looking for more of a rocker or hipster vibe…I'm also loving this plaid shirt / high-waisted denim pairing from Madewell. 


Again, a plaid shirt tucked into the high-rise denim (skinny this time), showing off a cool belt.  Her lace-ups are pretty spot-on, but if you are heel adverse (even wedge-heel adverse) flat lace-ups would look cool here.  Or a ballet flat.  Or an oxford.  Or a short boot.

But high-waisted denim can be tricky.  If you are busty (or saggy)…make sure that there are several inches of space between the waistband of the jean and 'the girls'.  You can always try a medium rise (like M's) instead of a true high-waist (like Madewell's pic).  The medium rise will give you the look of a higher rise, but is easier to wear.

While high and medium-rise denim does wonders for a slight muffin top, if you are still rockin' a pretty decent pooch these looks are T-R-I-C-K-Y.  Big hips, big bum?  High-rise can work as long as you are showing off a small waist, but a really apple-shaped mom? (hello, you post-partum gals) Yeah — we would be better off not tucking in that shirt.   

Sooo…you wanna be like M?  (Or like the very skinny Madewell model in the uncomfortable pose?)  Here's how…

To make M's outfit a bit more mom-friendly, find a shoe with a lower, chunkier heel.  I've been drooling over the entire Swedish Hasbeens line ever since Esther of Chinny Chin Chin turned me on to them…check out the red clog below:

To recreate the Madewell look, I've linked to the jeans, shirt and cool belt from the Madewell pic above.  And while I LOVE the shoes the model is wearing…my go-to shoes for this outfit would be ballet flats (I'm loving Banana's tan leather + denim ones below) or even a short boot for snowier days.

So tell me – what are your thoughts on the high-waisted denim?  Loving it?  And if so, would you show it off?  Or too scary?

And how many moms out there can rock a heel these days?  M does fairly consistently…but I cannot.  Waaaay too klutzy.  We wanna know!!  So if you are loving a slight heel, we'll start showing more…





About Author

Shana founded The Mom Edit in 2008. She lives with the love of her life (his name's Mike) and their two crazy boys in downtown Philadelphia. She loves a good styling challenge (her engineering side shows eventually), appreciates kindness, and usually picks scotch over wine, sneakers over stilettos, and denim-underwear, always.

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  1. The shoes I’m wearing here are actually paper-thin flats, which can be great with flares as long as the pants are hemmed right. The problem is they almost never are and flares are very unforgiving on length since they can’t be scrunched, tucked or cuffed. Flares shouldn’t pool around your feet–a sure ticket to dumpsville, but hemming can ruin the line of a flare really easily, so try to get something as close as possible to your inseam and that’s appropriate for your footwear, then get them altered by having the hems snipped off and reatatched to keep the look sharp. I pay about $20 for this little proceedure and it looks sooo much better than a traditional hem job. Call around to local tailors and ask them if they shorten jeans by reattaching the hems–if they have no idea what you’re talking about, skip that tailor and find one who does.

  2. Love, love, love the madewell outfit. Considering my Albertan cowboy would love me to rock a plaid shirt -I may just have to invest in all those pieces. What a shame 🙂

  3. I’ve adored that Madewell pic for ages! And this post might have convinced me to try my jeans with my shirt tucked in tomorrow–I’ll let you know how it goes.
    And I’m rocking a pair of high-waisted jeans right now, actually. They’re BDG High Rise Cigarette Jeans, and I am IN LOVE. Like, my favorite jeans ever. If you’re looking for a skinny hi-rise, get thee to an Urban Outfitters!
    And, sigh, I too have given up on heels with The Pup in tow. I still wear them to work, but I do almost all flats at home these days. I do, however, wear my heeled clogs often, and I find that my heeled boots get more wear too–maybe because the heels are chunkier than my pumps? I think the flats/flares will be much easier come spring and summer, as flares and sandals can be adorable–vintage and boho and feminine–in a way that just doesn’t work well with winter shoes.

  4. i love flats – and sometimes a bit of a heel – although not when toting my 2 yr. old (and 6 month preggo belly around)…my problem is with jeans being too long for my flats..i know i know…get them tailored…who has time?! and then…what do i wear when i do want a bit of a heel?! never satisfied – are we?

  5. I think M looks great! I love it!
    I wear heels to work quite often, and also for date/going out nights. I would like to see heels featured here.

  6. I cannot stomach the high-waisted jean (unless it’s used purely for utilitarian purposes, aka: unseen under a long shirt to control the muffin). In visible form, it simply screams, “80s mom!” in the worst possible way to me, even in the more contemporary cuts and colors. That being said, this could be because post-baby I’m working with permanent DDs, and I was short-waisted and torso-challenged to begin with. If I were longer and leaner and less curvy, I’d probs roll with it. This is one of those trends that just doesn’t work for my body, and I am very clear about that. 🙂

  7. People MAKE high waisted jeans these days? News to me! I always want a pair postpartum and can’t find them…tell me, do you suppose they’ve made it to Target or Kohls yet? That’s realistically where I can buy new jeans.

  8. I look for midrise – i don’t tuck in much, though. The midrise helps with tummy control well enough. I’m not against the highrise, but I think I’d want to keep a pretty tailored looking jean in that case – high rise trouser jeans can look elegant, for instance. Right now I’m picturing old-school mens’ wear silhouettes like on Katherine Hepburn or Lauren Bacall.
    Anyway – and heels. Yes, but not more than 3″ and wedges are better. I’m mostly flat boots & flats, though, when alone with the kids out & about.

  9. Nell – Ummm…I think the blouse is on sale? 🙂 If that helps.
    Amy – Great point. For some reason, I’ve been picturing flares in a summer setting, and dying for a lighter wash. We’ll see what I find. Let me know how the tucking goes. 🙂
    Lyn – I finally tailored my maternity skinnies (a while ago, when preggo)…and it was like a whole new world opened up. The nice thing about skinnies is that they still look good with heels even once they have been altered. But now that I’m no longer preggo, have I tailored the rest? Ummm…who has the time? LOL – I hear ya, sister.
    Mandy – Thanks for the feedback! We’ll keep it in mind…
    Maria G – Not all trends are for everyone. Good for you knowing which ones to skip. I’m going to have to sit out the high-rise phase as well, due to post-partum pooch issues. (BUT…FYI, the high rise does feel great on a c-section scar. )
    Sage – Not sure (Target is usually a bit behind)…but I just came across a pair at Land’s End Canvas on sale for $20:
    Jacci – Love the old-school men’s wear look. Nice.

  10. Heels yes! Love heels! If babywearing I go for flats or chunky/wedge heels, but I’ve rocked the stroller in 4 inch platforms for sure!
    I agree that with high waisted and flared looks the hem has to be perfect. For me, I like to buy really well made pants, of which one doesn’t need very many. The same couple jeans or slacks can make a ton of outfits. (I go for bargains and varietiy with tops/tunics/dresses.) When I find a pair of jeans or pants that fit absolutely perfectly, I’ll buy two pairs – one to hem for heels and the other to hem for flats.

  11. So for a very busty 5’2″ mama w/ c-section scar/permanent pooch, would these be a good or bad choice? Based on comments I’m thinking comfy but maybe not super flattering?

  12. I hope that Apple makes sure that the pull out scroll can lock into place, because I only know two people with four hands, and I don’t know how you would hold the thing open and use it at the same time unless you were one of those select few gifted with many hands.

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