The $100 Challenge: A Casual, Comfortable Chic Look for Fall (Dedicated to Erin)!


My friend, Erin, recently told me that she was troubled with finding a balance of comfort in her clothing, while still looking chic & casual.  Sometimes the fuss of too many accessories or a constricting belt & tight pants may make a casual look appear super stylish, but for the Style Darling wearing it, it probably doesn’t feel like the comfy sweatpants we all love to slip into after a long day working.  So, my goal for this edition of The $100 Challenge is to put together a look that could be described as comfy chic, dedicated to my favorite Mid-West dwelling Style Darling, Erin.

Since the seasons are changing & Erin is in Minnesota, she needs some layers to keep her warm, but at the same time, she’s a busy independent woman who needs to look stylish at all times. Some people look at ponchos are glorified snuggies, but this stylish poncho from H&M for $19.95 is adjustable, so you can show your figure, while taking advantage of the luxe, neutral shade to go with your jeggings or wide leg jeans.  If you’re not an earth-tone gal, the poncho also comes in black, available in sizes extra small to large. You can just throw it on when you’re feeling a chill, rather than trying to coordinate a jacket with a scarf & then adding a belt to cinch in your waist. Underneath the heavy knit is a draped sleeveless top from The Gap, which serves as a flattering base to any outfit with a blazer & pencil for a job interview, or with striaght leg jeans & suedewedges. The top is currently on sale for $18.99 from $29.95.

To me, when I think of comfy, I think of elastic. I mean, who wants to fuss with buttons, clasps, & snaps to fit into something, especially if you’re doing a lot of moving around?  Not I.  I’m not sure if Erin is a leggings girl (I am not, but I think they look really good with a tunic top of appropriate booty-covering length).  You can find leggings just about anywhere, but these black leggings from Forever 21 are only $4.50 & come in 8 other colors, including royal blue, navy, dark gray, & eggplant for your choosing. That’s a bargain & talk about variety!

I selected two different pairs of shoes, ballet flats & boots, b/c this look can instantly switch from minimalist preppy to polished urban depending one which shoe you go with.  The metallic flats cost $12.50, also available in all black, pewter, or navy. The patent adds a surprise pop of shine to the outfit, but also the delicate bow makes the look much more feminine & glamorous.  As for the plaid cuff boots from Payless, we’re heading into Sienna Miller / Alexa Chung style territory, for $39.99. You can tie them all the way up to cover the end of the leggings or fold them down to show off the plaid details.  Sometimes it’s all in the smallest details!

With so many big pieces going on here, I picked out two simple pieces of jewelry.  Since the poncho has some bulk to it & clearly doesn’t allow for a necklace, I picked out pearl studs with a rhinestone casing.  If you’re busy & on-the-go with your hair tied back, these soft studs will frame your face perfectly!  Also, the cutout flower ring adds some more detail & can be worn as a go-to cocktail ring for a variety of affairs.  Not to mention that both of these pieces only cost $3.80 each!

Part of what I love about the ring is how it’ll bring out the pattern in the CALYPSO St. Barth for Target tote.  It’s currently on sale for $6.98 (WOW!), marked down from $19.99, also available in turquoise. I thought that the brown looked a little more fall-appropriate & not so much like a beach bag.  The bag looks to be in proportion to the rest of the look.  Sometimes I hate seeing the skinny girls in their super tight jeans & tops carrying an oversized handbag, which looks to be weighing them down.

Of course the bag can also carry either pair of shoes that you choose, in case you need to switch, but I’ve done the math & if you only pick one pair of shoes for the outfit, your total will cost either $70.52 or $98.01, before whatever taxes exist wherever you are, of course.

Do you think this outfit is comfy chic?  What items of apparel do you own that you love to wear when you’re out & about & don’t want the fuss of heels & something form-fitting?  How much would spend on pieces like these?  What’s your fall go-to piece? Happy Styling!

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