Pair These Seven Pieces With Boring Basics To Nail That Pesky “Dressy-Casual” Look


Mamas, this article was inspired by a question I received from Martha.  She wrote:

I recently discovered your blog and I am loving the inspiration to step up my mom style a bit, and ideas for putting more personality into my basics. I'm realizing, though, that I have a weird gap in my wardrobe. I have plenty of casual mom clothes (jeans, basic tees and sweaters, comfy shoes). My work wardrobe for a casual but conservative engineering office is jeans, cords, or cotton pants, "boring sweaters", and flats or conservative boots. And I love the rare opportunity to rock a cute dress and strappy heels. But for some strange reason, even before I had kids, I've struggled with what to wear for a dressy-casual night out, like to a restaurant or parties with other "grown ups". 

It's true!  Dressing way up is easy: dress, shoes, clutch, done.  Wearing yoga pants is easy.  But nailing the dressy-casual vibe in an effortless way is tough.  It's easy to go overboard and end up with something that feels too fussy, too "done".  Or, on the other side (like at a business casual office) you end up wearing all solid-color basics.  Snore.  

In the past, I've done both.  Neither is fun, neither feel like "me".  But there are a few pieces that I find myself reaching for time-and-time again, whenever I'm in the dressy-casual zone, be it work or Play* related.  Keep reading to see both the list, and how I'm mixing up my own pieces.

(Play = Big Girl playtime and involves cocktails, play = kiddo play and involves dirt)



Stylemint Nicholls Blazer | Mango Lace Tee | Ann Taylor Floral Blouse | M Missoni Skirt | Topshop Check Trousers | Steve Madden Instantt Ankle Booties | Calvin Klein Pumps



Keep reading for a full explanation of the list, as well as some example pics of how I've been mixing pieces like these…

1. A Cool Blazer  

Wear this with jeans and a tee when going out, and for work?  It's obviously a no-brainer.  Just find a blazer that's interesting.  Try an updated shape or something asymmetric (like this one, on sale for $60).  Or look for cool details like leather lapels, or a bright pop of color.  Whatever floats your boat.  

This one still floats mine…it's hard to argue with sweater-sleeves.


(wearing:  Jacket c/o TMRDNL, Stylemint tee, Levis 535 denim leggings, 9 West Booties, vintage clutch)


2.  Lace Top 

I know this is a weird one.  Especially when I'm talking about both date night and an office environment.  But I've found that if you layer a lace top over a turtleneck and then—OMG somebody STOP ME.  I sound insanely dorky and am convincing no one.  (Except for fellow turtleneck lovers!! I know you are out there – holla!!).  Ok – let me just show you:

For Work…



…and Play…

(wearing:  J.Crew tissue turtleneck aka THE BEST ONES AND I'M KINDA A T-NECK EXPERT, Abercrombie jeans, MOOP's Paperback Clutch, Aerosoles pumps on sale for $20) 


See??  Not bad, right?  I'll swap out the turtleneck for a tank in the summer (yeah…I get crazy like that), and add a blazer if I need to be more dressed up for work. (Or I DID.  Back when I worked.)

(NOTE:  Nursing mamas, these are decent pooch hiders over a nursing cami.  Just find a lace top that's either boxy and short, or long and flowy.)

Also, if I'm feeling too fussy, carrying a low-key canvas clutch is my new favorite trick.  Mine is MOOP's Paperback.


3. A Pretty Blouse

I have one of these.  Like…ONE.  And it's now almost ten years old.  So I'm also in the market for a new pretty blouse. I'll pull together a little shopping post later in the week (or month) with a bunch of pretty blouses.  They are insanely versatile for both work and Play.  Mamas should have at least one. (And Everlane's new, affordable silk blouses will definitely be on my list!!) 


4.  A Cool Skirt

I always forget about skirts.  They often feel too dressy for most situations, and then when I want to really dress up, I put on a dress.  But in the last year or so…I've started to embrace skirts.  I like mine a little bit funky – a cool pattern, like the Missoni one above, or some awesome draping/ruching, like TMRDNL's Bunch Skirt.

Looks insanely cool (and effortless!!) with a basic white tee and booties.


(wearing: Everlane box cut tee – I'm wearing a small, skirt c/o TMRDNL - I'm wearing a small…this skirt is still available for $55, plus an additional 20% off with code ANMJ)


I also think that skirts like these, even if they are unconventional when compared to, say, a pencil skirt, can be worn to work.  I'd just keep everything else fairly…you know, serious.

No smiling.  This is serious bizznizz.



 5.  Crazy Pants

Sick of your denim?  BAM – DATE NIGHT:


(wearing:  Bow Back Top c/o TMRDNL, printed flares are 7's…found at goodwill for $4!!  Really.)


I love how this top is slightly sheer, yet drapes over the pooch, hiding any saggy skin.  Although, now that I'm staring…can you see my pooch?  Maybe?  GAH.  Moving on…



By keeping everything else calm, I think crazy pants work for work.  Of course, some Mamas may be more comfortable with printed pants.  Which are a slightly less insane version of crazy pants…but can't be as much fun.  *cough*LillyPulitzer*cough*


6.  Stiletto Ankle Booties

These were one of my Best. Purchases. Ever.  They are my go-to shoe for any cold-weather related dress-up or dressy-casual event.  For the last three years. And YUP – I wore these to the office.  I LOVE how they add an edge to cords.  Sheesh.  But they're just, you know…black boots.  Nothing fancy.


(wearing: all ancient stuff – JCrew blazer, MiuMiu silk blouse, JBrand cords, 9west ankle booties, warby parker glasses) 


7. Printed Pumps

Printed pumps are a pretty big trend right now, and with all of the pattern mixing, they are insanely easy to wear.  The key is not to overthink it.  You could get any pattern you like (floral, dot, etc.) but I'm still loving leopard print.  IknowIknow – it's so two/three/whatever seasons ago, but it inexplicably looks cool with everything.  The vibe strikes me as flirty and fun, rather than dressy.


(wearing: old blouse, JCrew belt, Aerosoles pumps on sale for $20, MOOP's Paperback Clutch,  AG Stevie Slim Straight-Leg Jean)


Ok Mamas, I'm done.  PHEW.  Thoughts?  What are your go-tos for the dressy-casual thing?  And PLEASE:  If anyone has come across any gorgeous silky tops, let me know!!




  1. I love a simple dress with thick tights and my Frye Melissa Button boots… and some kind of dressy cardigan and a scarf. It always looks cute and it’s comfy. It’s my favorite dressy-ish look for winter.
    In the summer I wear trouser jeans and wedge heels with a nice top and a blazer… usually looks cute and fun and not too over thought out.

  2. I love love love those crazypants. I love houndstooth, and Goodwill is awesome. I have houndstooth skinny jeans (rich and skinnys) that I bought at Nordstrom Rack for $40… not quite $4 but oh well…

  3. Love that black Mango lace tee! Might have to pull the trigger on it. Thanks, Shana! And loving the play vs. Play distinction. 🙂 For winter, my go-to top for “Play” is a grey long-sleeved sweater from Kookai. The front is a simple v-neck and the back is a beautiful sheer, silk in a purple/teal swirly combo. I like that its kinda like a mullet – serious in the front, party in the back. And for summer (or under a blazer), my go-to has been a Kenzie blue silk tank with a deep v-neck and beaded sparkly things along the neckline. I’ve been searching for a sexy black shirt, maybe with a deep v-neck and some pooch-hiding strategic ruching, with no luck. Would love some ideas! 🙂

  4. SEQUINS!! If it sparkles, I love it. I have a few vintage sequin jackets (those ones you see in the thrift store and immediately picture Bea Arthur wearing it on a cruise?), and I like to wear them over a rock tee, some skinnies or boyfriend jeans, and killah pumps. BAM – girls’ night out done and DONE.

  5. Loft has great basic silky blouses at the right price (and they’re always having a great sale), and Wyatt makes some nice ones that you can find occasionally on Bluefly.

  6. This post was perfect!! Thanks Shana! I just had an event with the hubs last week, and it was at a lounge (yes, seriously!) and the crowd was very urban and young. I spent hours trying to figure out what in the world I could wear that would look fun and hip, but not like I was trying to still be 25, especially since hubby was in a senior/leadership role. Funny, I’ve been on the hunt for both the perfect blouse (thinking cream or gray), and a lace top. I love the Mango one, but it’s sold out in my size. Thinking of trying this one…

  7. I’m thinking about getting the TMRDNL skirt. I’m 5’4″ and wear a size S. I’m just wondering how long it will be on me. Also, I couldn’t find on the website what type of material it is. Is it knit or woven? Thanks for you help and the awesome post!

  8. For me, I do dressy-casual one of two ways: casual with dressy jewelery, or dressy with simple or no jewelery. Also, a denim jacket does wonders in taking something too dressy down a notch.
    For examples, I’ll wear my nice jeans and a knit top with with a statement necklace or sparkly earrings. (This is a trick I picked up when I was living in Phoenix in 2007 where every woman at the mall seemed to be wearing 2 ct. diamond earrings with her yoga pants). Or, I’ll wear a dress with just plain stud earrings and a denim jacket.

  9. In the winter I usually wear a sweater dress with tights and boots for Play–its comfy and I’m covered. But my year-round go to is the blazer (a black BCBG from more than 10 years ago) with a silk tank/blouse, skinny jeans and heels in a fun color. I pray that jeans and heels never go out of style. They probably already are; I did make the switch from boot cut to skinnies a few years ago, I’m not sure where to go from there.

  10. I love this post, and I’m also loving all of the comments about what other people wear. I have to admit that once I find a ‘going out’ outfit that I like, I then wear it to death with the different groups of people that I go out with. It works out great because I only have to think once for 3-4 occasions.
    I just clicked on the link for the paperback clutch and it looks like the perfect bag! I love it as a crossbody and a clutch.

  11. I love this post for closing a huge gap with pieces I actually own! And the work options that don’t involve a suit are so clutch for freezing sloppy winter weather- thank you!
    My Play secret is a pair of tall moto-inspired boots I’ve had forEVER. They make the basics (little black sweater dress and tights) a little sexy and a lot badass.

  12. The great thing about denim these days is that anything goes. Literally. Boot cut, wide leg, boyfriend, skinnies, ankle length, you name it. Get thee to a Gap (or similar denim temple) and try everything on until you find something else you like. 🙂

  13. Aaahahahaha, that doesn’t sound like Phoenix it sounds like SCOTTSDALE. For non-ArizonaDottsdale mamas are the ones running around in their Lululemon and $300 blonde job and fake tan and status jewelry.

  14. In a case of total fashion karma, the day after I read this, I found a lace top almost exactly like yours at Banana Republic for $20. Twenty. Dollars.
    You *know* I bought it.
    (Wearing it today, in fact. With a turtleneck, obvs!)

  15. Shana, I need your help! I’m planning on buying the Aerosole Tapestry Pumps (3 pairs in red, blue, and purple, yes I am crazy), but don’t know if I should buy my regular size or a half size up due to some of the reviews online stating the toe box is a little tight. Please give me your opinion. Thanks.

  16. I debated that too.  In the end, if you wear them a ton (and I do) they stretch out.  I'm glad I stuck with my usual size, since I hate when the pump is too loose and end up walking out of it.   Good luck!
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  17. Thank you so much for giving me your advice and responding so quickly! You are the best. I seriously sweat your style and already have the Clark’s booties (I was already a huge Clark’s fan). They are super comfy and I wear them all the time.
    Btw, now that you are in Philly (my Dad’s home-town) I have to recomend Fiesta III in Chestnut Hill for the best Cheesesteaks. Pat’s and Gino’s are terrible. Jim’s Steaks on South Street is also classic.
    Thanks again!

  18. Shana, a very belated thank you for this!! I love all of it. You’ve got me on the hunt for the right lace tee, and I can’t wait to see what other blouses you come up with! Might even have to find some crazy pants.
    Also, to add to the cheesesteak discussion, I lived in Manayunk and Havertown for a few years, and loved Dalessandro’s in Roxborough 🙂

  19. I pre-emptively ordered the everlane silk blouse in white with blush detail. Best purchase ever the silk is thick and soft and perfectly drapey. I have paired it with wool pants for serious time and half tucked it into faux leather leggings as pants for hot hot date night. I am taking it with me to wear at a conference to. Buy this shirt!!

  20. I’m always looking for cotton/stretchy but structured blazers, especially ones with 3/4 length sleeves. Great year round from long sleeved something peaking out on the lower arm….Great really for spring, fall, summer especially with summer AC worn over a tank. The arms aren’t as stiff and it gives so when your arms are bent at a key board you don’t feel that arm bend constriction. Plus it can be a tad more on the casual side for my office which is more of the casual of “business casual” Worn with some jewlery, long jeans and heels or boots works for the dressier, but also dresses up some cuffed jeans and more casual jewlery with ballet flats!! Loving this site and thankful I found it through my art school friend, and you’d new contributor, Laura!!

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