$98, netaporter.com

This pajama top's vibrant hue and red piping make it too cute to keep in the bedroom. Work it as an effortless out-and-about blouse that goes with everything from casual jeans to a structured leather pencil skirt. On any old hot summer day I'd wear it, sleeves rolled up, with...

1. Juicy satin pajama top,
2. Topshop sunglasses,
3. Madewell canvas tote,
4. Old Navy leopard print ballet slippers,
5. J. Crew denim shorts,

$225, jcrew.com

On Saturday evening, my husband and I and two other couples went to Malibu Farm, owned by chef and author Helene Henderson. She stages quarterly 80-person dinners in her four-acre backyard, filled with goats, chickens, lush orange trees and vegetable gardens. (Most of the organic rustic-gourmet fare is made from the just-picked herbs and vegetables grown on Henderson's farm!) The only hitch to the fantastic evening was figuring out what to wear to the farm. Flats and jeans, for sure, but since the dinner was al fresco, and knowing how Malibu can get very chilly at night, I wanted to wear a blouse that looked summery and festive and yet was easy to layer. I so wish I had this vibrant print tunic, because it would have been perfect for the occasion. But now I am thinking it will work some magic on July 4th, paired with shorts, of course...

1. J. Crew silk print blouse,
2. Eugenia Kim hat,
3. Linda Farrow for The Row sunglasses,
4. Nine West feather-trimmed sandals,
5. Old Navy cut-off denim shorts,

$110, topshop.com

We shot Lucky's August cover this week, and the stylist was, not surprisingly, the epitome of cool. She was wearing leather shorts, a black and white checked button-down shirt (a small subtle print), coral lipstick, with, get this, a tiger print blazer from Zara and Chloe's studded ankle boots. The outfit was straight out of The Sartorialist. But while I was in awe (AWE!), I also felt that I could never, ever pull off the same look, especially the leather shorts (as much I wish I had the legs to do it, or the courage!). So, herewith, today's outfit. It's inspired by the uber stylish stylist, but very much watered down, so that one (um, me?) could wear it everyday without feeling like a loser wannabe! P.S. I will not lie to you: looking chic is as easy as wearing this pajama-spirited blazer.

1. Kain silk tank top,
2. Topshop pajama jacket,
3. Giles & Brother rose earrings,
4. Poppy King for J. Crew lipstick,
5. New Look studded boots,
6. J. Brand shorts,

$22, riverisland.com

On those crazy days when I have activities scheduled morning to night and there is no time to change in between, I will look to these shorts for a bit of help. That's because they can take me from camp drop-off to a photo shoot to drinks with co-workers. Here's how I'll wear them from day to night, this summer:

1. Madewell silk blouse,

2. Superfine jacket,

3. Loeffler Randall sandals,

4. River Island beaded shorts,

$53, warehouse.co.uk

I think the whole dressy shorts trend can be a bit treacherous. For example, you don't want shorts that are too short, especially if you're wearing them with heels. And if you are wearing them with heels, it's crucial that the shorts are polished-looking. These floral shorts allay any fears. They're flowy and mid-thigh length, almost skirt-like. And the floral print keep things sophisticated and feminine. Wear them all summer long with..

1. Oak asymmetric satin blouse, 

2. Alexander Wang washed leather bag,

3. Rebecca Minkoff suede wedges,

4. Warehouse floral shorts,

$298, oliviarubin.com

No need to wax on about the merits of this jacket, because the details--the peplum, the studs--speak (highly) for themselves. But I will say this: it's an all-purpose statement piece that can enhance any outfit. Plus, it's by London High Street designer Olivia Rubin, who is relatively unknown in the US, which lends it a sort of inscrutable, European air. Wear it with jeans, dressy black trousers, or try something a little East Village-unexpected and pair it with...

1. Olivia Rubin blazer,
2. Topshop peplum top,
3. Jerome Dreyfuss snakeskin and leather bag,
4. Rag & Bone boots,
5. Thakoon printed crepe de chine shorts,

$148, anntaylor.com

Sometimes when I am getting dressed in the morning and feeling uninspired (or overwhelmed), I choose an accessory first and dress around it. Going for a statement necklace like this further simplifies things because it becomes the outfit's focal point, which means the rest of the outfit can be rather basic. Made with pops of neon and robust rhinestones, this Ann Taylor choker gets it right. Wear it with..

1. Acne silk and cotton sweater,
2. Ann Taylor necklace,
3. Topshop clutch*,
4. Madewell sandals,
5. Juicy Couture shorts,

*This is actually an iPad case, but can be used as a clutch too. Genius.

$118, jcrew.com

J. Crew cleverly reinvents a pair of khaki shorts with a feminine scalloped hem. (Just FYI: these are my ideal day-to-night shorts: great with a lived-in white t-shirt or a statement blazer.) I'd wear it with...

1. 10 Crosby striped tank,

2. Callula Lillibelle oversized satin tuxedo jacket*, 

3. Givenchy buckle sandals,

4. J. Crew scalloped shorts,

*Push up the sleeves on the blazer to effect a more casual vibe.

$22, oldnavy.com

This summer's stalwarts (and for the rogue LA heat waves in between). Wear them with...

1. Paul & Joe cotton sweater,
2. Cutler and Gross round sunglasses,
3. 3.1 Phillip Lim leather tote,
4. Mango sparkly sandals,
5. Old Navy printed shorts*,

*Old Navy's shorts tend to run small, so I always order a size up.