When it comes to test driving out new trends each season, I like to approach with caution. After all, I have 7 years worth of content to prove when I should and, perhaps more often than not, shouldn't have tried out a few fleeting styles (cue the uncomfortable cringing now). But when the folks over at Who What Wear ask you to try out a few of their stand out favorites of the season ahead, you can rest assured it's been street style vetted and stamped with approval. So, of course you say yes.

As part of their 30-day fall wardrobe challenge with Saks Fifth Avenue OFF 5th, their editorial team asked me to tackle two stand outs, that being chokers and cropped flared jeans with block heels. Granted, I've seen more than my fair share of both lately and I love the look on some of my go-to street style stars, but admittedly, wasn't sure how I'd pull either off. Both trends push me slightly out of my comfort zone (I'm a sucker for dainty gold jewelry and a skinnier stiletto heel) but sometimes it's necessary to shake things up. Or at the very least, surprise yourself from time to time.

What I love about Saks Fifth Avenue OFF 5th, especially for a challenge like this, is just how many current season items are available at a reduced price -- it makes investing in some of the trends ahead easier to digest (sartorially and financially). And much like my mom, who taught me at a young age how to navigate stores like this, I can easily spend all day browsing through the racks (and on numerous occasions went off course), but I stuck to my task at hand. Chokers. Check. Cropped denim. Check. Block heels. Check. I was on a mission. And I refused to fail.

I started first with the chokers. Because, accessorizing shouldn't be that tricky, right? Right?