A cute and comfy fall OOTD often consists of a cute sweater, jeans, and boots. While this may be a simple style formula to follow, I’ve been thrown off by shifting denim and boot trends. Read on below for how I’m adjusting to the new decade’s trends, while still going with what I personally like.

  • A Cute and Comfy Fall OOTD How To Adjust to 2021 Fashion Trends
  • A Cute and Comfy Fall OOTD How To Adjust to 2021 Fashion Trends 2
  • A Cute and Comfy Fall OOTD How To Adjust to 2021 Fashion Trends 3

1. Explore new denim cuts.

Suddenly, my stacks of skinny jeans are taking a back-burner on the ever-changing fashion stove that burns trends and revives them decades later. I’ve been switching it up with a cropped, distressed straight leg pair of jeans that I found at T.J.Maxx or Marshalls a few years back (call me cutting edge). They are the brand Kensie, and they are incredibly high-quality, stretchy, and comfortable. Since they’re a lot more breathable than skinny jeans, these are my favorite for transition seasons as well. This is the only pair of non-skinny jeans I own, so I just ordered a couple other Kensie styles that are on sale at Saks Off Fifth to try them out. Here’s what I ordered:

Kensie High-Rise Slim Fit Jeans via Saks Off Fifth

Kensie High-Rise Crop Straight Leg Jeans via Saks Off Fifth

Kensie Distressed Slim Straight Jeans via Saks Off Fifth

2. Break away from black boots.

There’s this one particular style of over-the-knee style black boots that I’ve worn for at least six years now, and I’ve been overdue for a change. While black boots go with a ton of outfits and can make something look more dressed up if in a certain style, they are really harsh for daytime. I’ve been going for more natural, softer, and brighter looks (also, lots of floral prints). With that, I’ve been looking for booties that are a natural taupe color. After ordering and trying on a few, I discovered the most comfortable and adorable pair from Lulu’s. The pair comes in three different colors, but my favorite is taupe. The heel feels just the same as a very low heel to me; they are comfy for long periods of time and easy to walk in.

Lulu’s Shasta Taupe Suede Ankle Booties

3. Opt for comfort.

The idea of an underwire push-up bra is painful now. While I still wear real bras for more formal occasions or for certain garments, I live in lounge bras on a day-to-day basis. Here’s my favorite pack of black, white, gray, and nude from Amazon:

Amazon Seamless Bralette 4-Pack

Since the bralette looks like the top of a camisole, it’s okay if a strap or the neckline pops through your look. In fact, I love wearing these bralettes underneath what would be a low-cut shirt to make more modest. I also think it’s cute if a strap makes an appearance for a casual, off-the-shoulder look.

In line with outfitting for comfort, oversized sweaters pair nicely with bralettes. I’ve been loving the trendy twist on a classic black and white sweater Sussex Fashion Co. sent me. The lace up detail on the sleeves is my favorite! This shop is launching soon, so stay tuned for it’s unveiling! In the meantime, I’m linking to a similar sweater that is a high-quality Amazon find:

Good Threads via Amazon

Last, but not least, I can’t forget my black Scrunchie! I’m so glad Scrunchies have made a comeback. They’re far better for your hair than an average hair elastic, and they can spiff things up. Here’s a few different packs:

Jumbo Scrunchie Pack – Velvet and Satin (Fall Colors)

Scunci “The Original” Super Comfy Waffle Knit Scrunchie Pony Holders

Scunci “The Original” Velvet Scrunchie Hair Ties & Pony Holders


Thanks for dabbling in a cute and comfy fall OOTD with me – I hope you found some style inspiration! It’s always nice to freshen up your wardrobe, especially when the new pieces practical, and something you’ll wear every day.

If you’d like to explore more of my fashion posts, here’s another fall OOTD with stoppable pieces!


Dabble Daybook is a participant in the Amazon Services LLC Associates Program, ShareASale, and LikeToKnowIt, affiliate advertising programs designed to provide a means for sites to earn advertising fees by advertising and linking to products. Dabble Daybook was also gifted the sweater from Sussex Fashion Company.