Style and the Second City

So before we get started here, let's just state the obvious.  I have been a complete and utter slacker.  Rather than bestow a wealth of fashion knowledge on my many loyal followers (thanks, mom!), I've been drowning my sorrows away in fabulous outfits and dirty martinis over the impending post on the very bane of my existence: leggings.

Why, WHY Lindsay?  Why do you put me and Anna "Golden Mecca of Bobness" Wintour to shame?  It is officially the trend I cannot escape.  My, oh my, it sure is chilly in the L.A.-90-degrees-in-November-HELLO-GLOBAL-WARMING air, better throw on my leggings to survive this cold front!  And nothing says frigid Chicago weather like assuming a thicker version of tights will replace pants.  Leggings do NOT REPLACE PANTS PEOPLE.  Does no one remember Sue Ellen Mischke?  This is the modern day equivilent of wearing a bra as a top!!

Ahem.  So, in a tribute to painful trends that we sometimes refuse to let go of, I went desperately seeking some fashionistas who could pull it off.  And if there is one place I know in this city where there could be a tiny glint of hope, it's the home of my future walk-up and Mercedes sedan, the Gold Coast.  This one's for you Schnitkey.

What hurts me the most here is not what I'm seeing from the front.  Not the blatant wearing of shower shoes on the street (honey, did you come straight from getting a pedi?  No?  I didn't think so.), not the second worst trend of all time that you have thrown in my face - the "summer" scarf that serves NO PURPOSE - nay, what really burns my chaps is that she is subjecting the poor baby behind her to her tookas wrapped in a package of LEGGINGS ARE NOT PANTS!  

See, now you've gotten me all fired up again.

And then girlfriend had to go and do this to me.  When I said leggings are not pants, this is not where I was going.  Dearie you BETTER put on those shades, because it's gonna be a looong walk of shame down Oak Street.

Oh, really?  Because the last time I wore leggings that had lace on them I wore them with coulottes and a t-shirt with a dickie underneath it.  A DICKIE.  That's right, you may have thought I was wearing a turtleneck under that t-shirt, until I defied the laws of physics with - look, no sleeves!  Do you really want to go back there?

And in a final act of trend-death-defiance, we have these.  BROWN leggings.

I can't.

Even my first do's scrumptious Chanel bag distracted me to the point where even I overlooked the glaring, dreaded, black/brown clash happening before my eyes.  And yet in a sea full of pant-replacing, Jennifer's sweater mini is the perfect length to wear her leggings as they should be worn, as tights.  Let's face it, with hair like that I can overlook a mistake here and there.   And she would have looked FIERCE if these boots were in a fall eggplant or jewel tone blue.  Hit up these leggings at every bargain trendster's fave - Forever 21.

Now THIS is how you make layering work.  It's not over the top, and Muriel makes her Express leggings more of an afterthought with perfectly placed accessories that pull it all together.  Her top just barely meets the SATSS crotch-covering requirement, but she looks fantastic and effortless, perfect for a day of Chicago-chic shopping. 

Ciao for now!

Ah, Lincoln Park. Home of frat daddies and beachcombers. Diversity! 

As I strapped on my stalker camera I thought to myself, of all the glorious Chicago neighborhoods, what better place to spot sexy shoppers and post beach hotties working it in the summer's breeziest trend?

Enter, the maxi dress. This one is tricky. I'm all for the effortless, beachy cool yet totally feminine and sexy look that a maxi gives, say, Blake Lively. But let's back up the jolly trolley for a minute here. Let us not forget how painfully hard J. Simp has been trying to make this look work for her with her 4 inch foam shower shoes hiding underneath. Honey, you aren't fooling anyone.

Let's just be honest, this look ain't for the shorties. (But while we are on the topic of footwear, who didn't rock a pair of those unfortch thick black flip-flops from J. Crew back in the day? VINTAGE! Am I right?!)

But I digress. Let's review the many ways to wear it wrong that the L-Pizzle had to offer:

I call this print, "The Flowers We Lost in the Fire."

Oh dear. You know, it's really just sad to see what could be a hot bod lost in a pattern that is burning my retinas. This dress has a great shape, and if she had chosen a solid color to complement her creamy and cancer-free skin it would have totally worked. Except for one thing. Who can overlook the fugly hat in the room? Is it just me or is this screaming A. Simp - aka Simpson "the lesser"? Is Papa Joe in town?! WHERE AM I?!!

Ahem.

Then there is this: 

Let me start by saying that I love this color on her. And she has the tan that I've been shamelessly pursuing at North Avenue beach all summer. And I would even say that she is almost pulling off gladiandals here. ALMOST.

Now, I get it. Alterations are the miz. But when it comes to dress lengths you have to make a decision, and this pseudo-maxi length just doesn't work. A mid-calf length tends to cut off the frame rather than elongate it, and it's got no love for even the slightest of cankles.

And then there is this: 

Okay, so in Lincoln Park the proximity to the lake allows for some leeway. But one of the biggest mistakes you can make with a maxi dress is treating it like a beach cover up. What if this was your Vicki's peeking out? What would your mother think young lady?! Just pull it together already.

And speaking of mothers, who would have guessed that the people sporting maxi-mum hotness would be the LP mamis, REPRESENT.

It is worth noting here that Patti is old enough to be my mother. In fact, her daughter looked equally as fierce in a maxi dress of her own, but here at SATSS we do not discriminate and Patti looked bangin' for ANY age. Love the print, and it fits like it should, fitted at the top and just flowy enough as it falls down at the appropriate length. And what's more? She got it at Target. Owned it.

I have to say that this picture simply does not do Dawn the justice she deserves in her adorable Ella Moss dress. I loved how it's as if she just threw this outfit on and yet she manages to look perfectly chic. The understated wooden earrings are a great touch, and the colorblock pattern really pops, without overpowering her (throw on a cardi and poof! - instant fall update). Dawn has officially proven that when worn right, the maxi can work even for petite frames - and look, no heels!

Yes, that is her tow-headed daughter hiding, and everyone knows that toting your gorgeous offspring is a do any day!

Ciao for now!

Let's start this post off by establishing that gladiator-inspired sandals, or gladiandals if you will, are EXTREMELY difficult to pull off. Few people wear them with confidence and even fewer get the look right.

That said, as I strapped on a pair of sky-high, and inarguably fierce gladiandals at Bloomingdale's on Friday (shout out to Danielle, shoe genius, HOLLA!) I knew that they were a must have. That, and the fact that everyone's favorite eternal bob-wearer and royal editrix of Vogue has thrown them at me with such a vengeance that I know I won't be able to escape the trend for at least another season.

Moving on, after purchasing said shoes, my mind immediately drifted to the many ways that I would have to reinvent my wardrobe to work with this tricky trend, from toenail colors to jewelry. I knew if there was one place to seek fashion inspiration for an item like gladiandals, it was by carefully monitoring the crowd in everyone's favorite hipster haven - Bucktown.

Shall we begin with the don'ts?

Oh, honey. We of the height-impaired variety must stick together and ankle straps are simply not kind to us. For shorter frames, choose a gladiator with a heel to propel you upward instead of pulling you down.

Even girlfriend behind her seems to be confused by this look. I'm all for adding in a splash of color, but these shoes just seem all out of place with this otherwise monochromatic ensemble. I keep looking at this and thinking, is that a t-shirt? A dress? Should I have chicken tonight or sushi? I've already moved on...

To:

If I could avert my attention from her painfully-constricted and nearly-visible lady bits for just a minute, I would note that I really wanted this look to work. I sort of covet her legs, and yet, I'm still in pain.

Looking back on my quest for gladiandal greatness, at this point I had become both discouraged and lacking in my own confidence in foraying into this trend.

Until this:

Hello, adorable and effortless! My new friend Jessica's look is simple and chic and the shoes become an interesting detail without overpowering her outfit - or her frame. Jessica nabbed this adorable Sam Edelman version from Nordstrom. Love and love.

Just when I thought that my mission was complete, I spotted another "do" that I had to share.

I loved Christine because she looks so fresh and summery, and her gladiators (purchased at Aldo) finish the look off with a perfect touch of the Urban Outfitters brand of cool. Perfect for a day of spending on Damen or drinks alfresco. SUCCESS!

After all this shoe scoping, I think I need an alfresco drink myself...and an evening of pondering if it's too soon to change my toenail color to black. Ciao for now!