A couple of things to keep in mind:
1. You don't need a lot of clothes to look and feel good.  It doesn't matter if you wear the same outfit over and over.  Who cares? As long as you look and feel good.  So while you're getting back to a weight you're comfortable with, make the clothes that fit you work overtime.
2.  Keep it sleek and simple!  With a new baby, the last thing you need is fussy style.  In the collages below I went for outfits, shoes and accessories that were easy to get around in, and work multiple ways. In fact, I lost count of how many different ways you could pair everything!
3.  Accessories make any wardrobe feel fresh.  They're inexpensive ways to get a completely new look. Slip on a bold necklace or cuff bracelet and earrings and you'll be simply stylish in a jiffy.
4.  Shoes make the look!  You're hauling a diaper bag with you, so rotating a bunch of purses into your outfits is impractical.  But shoes?  SHOES make all the difference.  They take a simple tank and shorts to a whole new level.  Your existing wardrobe is quite simple (mostly knit tees, tanks and dresses) so add some oomph with your footwear and jewelry instead of going out and getting a bunch of button down blouses.

Here are a few suggestions using just 4 accessories. 
You could also put the crystal necklace and earrings with the all-white outfit and pop it with some colorful shoes!  Or do the same with one of your black tanks, black capris and head out for the evening. Monochrome with pops of color looks very put-together, even if the clothes themselves are casual.

Here are some color combinations you might not have considered.
Gray and white together are surprisingly chic. With the silver/crystal accessories and a bold shoe - fantastic!  A contrasting shoe with any of your sundresses is something you'd look great in every time you step out the door.  And bright blue and orange are a very happy combo! The wooden bracelet echos the earthy tones of the olive cargo capris.

Like I said, I lost track of all the outfit options you have.  I could have created 5 more collages but I'd have had mutiny on my hands with my own daughters.  So here are a few more suggestions:

• I'm assuming you have a pair of black heels.  Hopefully something above a flip-flop/below a stiletto that you can wear during the day. Pair any of your black and white items together for a simple and chic combo.  Make it dressier with the crystal/silver accessories, slightly more casual with the colored accessories.
• Your maxi dresses and sundresses are great for showing off all the parts of yourself you're happy with.  And don't be afraid to bust out that black Grecian dress.  It doesn't have to be reserved for date night. Colorful accessories, not too-fancy shoes, a slightly un-done ponytail and you're good to go anywhere. (Never be afraid to look better than everyone else!)
• Your pink tops are inherently feminine - pair them with your tougher cargo capri's and a yellow, black or metallic shoe. I love the juxtaposition of masculine and feminine. If you have a studded sandal or belt - throw that in the mix! 
• Nautical color pairings are always a nice look - your blue shirts and white shorts work well, but pick any of the other shoes besides red or you'll cross over into Independence Day territory.
• I don't know how cold it'll get in Hawaii this fall and winter, but a bright cardigan (maybe violet? yellow? or light blue?) would look great with your coloring and work with all the neutral items you already own. 
  
• You mentioned you planned on doing some shopping after a few more pounds were lost, so I'd suggest looking for a structured skirt to throw into the mix.  A dark pencil skirt would add miles and miles to your wardrobe. (Not too tight and hemmed to your knees and it'll add miles to your legs as well!) With a t-shirt and sandals it's a cut above shorts and capris.  With your sparkly black tank and heels it's perfect for fancy date night! (Use those crystal/silver accessories!)
  

I hope this was helpful.  Thank you so much for asking a great question!  This was the first post-pregnancy style dilemma I've received.  I'm having fun working on the answer to your second question about traveling with a diaper bag.  Goodness, I haven't gone anywhere without mine since 2007! Look for that soon!
And the rest of you, don't forget to click over to Psyched for Style!

You probably didn't need to be reminded but just in case... the fabulous Nordstrom Anniversary sale started on Friday!!  And ends August 2.
Click the pic and head on over!  This sale is so wonderful. 
It's true sale prices on NEW fall clothing. 

Here are a few things I'm drooling over. 
It's $170 off the regular price still out of my budget range.

So cute and very similar to the red bow-neck dress Emma Pilsbury wore on Glee this season. (Love her wardrobe!)

I saw both this and the gold version in the store and was really drawn to it.  The sequins are very matte, which is cool.  It's my favorite sleeve length and I'd love this for date night!

This one, because I lust after wrap dresses with elbow-length sleeves and not-too-low/not-too-high necklines!!

Because I really love what the curved lines of this scuba inspired leather jacket will do for a midsection!

A sweet ruffled cardi in a lovely pale peachy/pink that is sadly already sold out!

So go have yourself some fun!  And keep in mind this little shopping tip - the new item must either Fill A Hole in your wardrobe or Replace something worn or ill-fitting.

Let's start off the week with a Modest Moment from Zoe Saldana.  Zoe is wearing a cute  Louis Vuitton frock.  I love the shape of the dress!  I'm a sucker for a full skirt. 
But I think the shoe choice was wrong.  As discussed a few days ago - I'd have to chalk these up as angry shoes. 

Our next feature for Dress Your Man is all about shoelaces. 
(cue sound of cricket and a dog barking in the distance) 
Huh?  Shoelaces? 
Yep.  Shoelaces. 
Those oft forgotten, mundane little strings that keep shoes on our feet but can instantly make a man appear juvenile when left untied in a business meeting.

I was inspired to write a shoelace post when I came across an article about the various ways spy's used to communicate with each other. (And still may!)  If you have young boys - how cool would it be for them to devise their own shoelace signals!

I'm an 80's child and definitely enjoyed the multicolored shoelace trend.  While I don't suggest a return to that as a way to personalize your husband's wingtips, an interesting lacing method can add subtle visual interest.  Men don't have many accessory options so unique, stealthy ways of owning a look are signals of real personal style.

And I found a fantastic website for you!  Ian's Shoelace Site!  I've had so much fun perusing his site. The clear pictures make copying that lacing method a piece of cake.
 Here's a little preview for you.

There are 33 lacing methods on the first page alone!  Then a slew of bi-color and lug lacing methods, lacing comparisons and reviews and even tips for lacing problems.
So go have a little fun with the shoes in your house.  If your man is like my man - he's just to cool for standard boring laces!  I think it would be great fun having the men in your house choose a favorite method and learning it together. 
(And please - shine the shoes before they sport the new laces!)

I'm a shoe girl.  Never been a bag girl.  Not a mountain-of-accessories girl. 
Unequivocally a shoe lover.  For me, one dress + 14 pairs of shoes = 14 different outfits.  But something has been niggling me about certain styles of shoes we've been seeing a lot of and I've finally found a definition for it!  Thanks to the following quote from Tom & Lorenzo and their "fabulous and opinionated" critique of fashion and style. 

"Let's all light candles and pray for the end of 20-lb. shoes of anger. We're tired of starlets walking the red carpet looking like they have bear traps on their feet."

That was it!  (After all, aren't we all starlets?)  I've been confounded by the "bear traps!"  The "angry shoes!" The "horses hooves!" Below is a perfect example...

Bear traps.

GRRRR!!!
Extreme bear traps!
Seriously angry shoes.

Not angry shoes.

Grouchy, clomp-clomp horses hooves.

(And not because of the wedge heel.  Wedges are great!)

Happy, walking-on-air shoes.

I don't think it's a color issue because, look!  Nude bear traps!

And I don't think it's a strap issue, because I wouldn't call these angry shoes.  Nor bear traps.  (Would you?)

It seems to be more the "weight" of the shoe - both visually and literally speaking.  A shoe could be made of neoprene and technically weigh nothing but still look heavy and hoof-like on the foot.

I've been loving all the 40's and 50's silhouette's that designers have been tapping of late.  And I like pairing a retro style with a modern shoe.  Keeps the outfit from becoming a costume.  I don't mind a sturdy shoe.  It can add a necessary touch of toughness to an otherwise frilly outfit and looks great with jeans and trousers.  I even like aggressive shoes, on occasion.  They can be unique and fun.  But Tom and Lorenzo hit the nail on the head - too often the shoes come off looking angry and at odds with the rest of the outfit.  Take the below ensembles as an example...

See what I mean!  Truly, "bear traps" and "angry shoes" are perfectly accurate descriptions. So what are your thoughts?  Are you digging the angry shoes or hoping they disappear? Are they the perfect shoe to grab for those times when you're listening to Alanis & Jagged Little Pill?  Or do they not really have a place in your closet and you opt for feminine footwear?  Me, I'm in the latter category.  I just don't find myself drawn to them. I'll admit, it's a very fine line between aggressive and angry shoes, but I prefer feminine, flirty, sexy, retro and unique over bear-trap, growling, horse hooves. 

And a final note... just in case you were thinking it.

Lightening up in the footwear department doesn't mean it's acceptable to wear flip-flops everywhere.  That trend (thankfully!) died over a decade ago.

Save these for the backyard and beach.

Whew! It's been a busy week, let me tell you.  Even a mini vaca over the 4th of July weekend is rough with 3 kids under 3.  Someone please tell me it gets easier when they're at the age when you can just throw them on the floor with a sleeping bag.  As I tackle the laundry, I'm also back to blogging. 

The little poll (and I probably shouldn't have launched a poll before a holiday weekend) came back overwhelmingly in favor of "They're comfortable and fine to wear as ultra-casual. Knee-length can be chic." 
So if you're going to wear them, here are some helpful tips.

 

NEVER wear denim cut-offs so short that your bum cheeks (or the front pocket linings!) peek out. 
Not even if you have a swimsuit underneath. 
Not "just at the beach." 
Never. 
This look says "trashy" in all the ways it can be said.


But don't go below your knee cap, either.  The denim capri is usually much less flattering than the denim short.

Do add a heel!!

A nice wedge sandal can take you from "I've just been cleaning the house and don't care how I look." to "I was just cleaning the house but you'll never know it since I look cute while running a few errands."

Don't fear the DIY. 
Have a pair of too-short jeans still lurking in your closet?  You know the ones.  The high-water/ankle-length Mom jeans?  If they fit you well in the hip, but and thigh - cut 'em off! 

And dye them a nice dark navy or black if they're a light wash.

DO stick to a trim fit, even if you're curvier. 
Wide leg shorts don't slim, they widen.  Same goes for capri's.  The principles of a hip-slimming wide-leg jean do not apply here.

Trim Fit does not mean tight.  It means skimming.  It means slightly camouflaging areas you want to hide and flattering areas you want to enhance.  

While I'm crafting the follow-up to the Jean Shorts Poll, let's enjoy a Modest Moment from Eva Mendes.  Eva is sporting a lovely spring frock from Christian Dior.