Dressing for Fall


It’s here!! My ultimate Fall wardrobe edit – with 25 pieces and 25 ways to wear them! There are a lot of exclamation points here because I’m truly excited to share but equally excited to be done with this project because it’s taken me quite a bit of time (watch the IGTV video with all 25 outfits come to life to appreciate the full effect). Regardless – I’m happy to have it out in the world and hope that it inspires you to pick up a great new staple for the season ahead or think of new ways to wear the items already in your closet. The world is a wild place these days but getting up each item and putting on a real outfit sparks joy for me, so I’m going to keep doing it. I’ll be wearing these outfits this fall everywhere from work Zoom calls to weekends adventures to an al fresco date night or two. Happy Fall friends!


Shown Above: Sweater Dress (size small) c/o | Wool Coat (size 4) c/o | Ankle Boots | Silk Scarf c/o

Shown Above Left: Cardigan (size small) | Flare Jeans (size 26) | Saddle Bag | Leopard Sneakers

Shown Above Right: Cardigan (size small, worn backwards and off the shoulder) | Leopard Belt c/o | Denim Skirt (size 4) | Knee High Boots c/o

Shown Above Left: Quilted Coat (size small) c/o | Sweater (size small) | Headband | Leggings (size x-small) | Ballet Flats c/o

Shown Above Right: Sweater | Flare Jeans | Burgundy Bag c/o | Silk Scarf | Knee High Boots

Shown Above Left: Plaid Shirt (size small) | Cargo Jacket | Saddle Bag | Corduroys (size 2) c/o | Ankle Boots

Shown Above Right: Plaid Shirt | Flare Jeans | Burgundy Bag | Ankle Boots

Shown Above Left: Cargo Jacket | Vote T-Shirt (size small) | Headband | Denim Skirt | Ankle Boots

Shown Above Right: Vote T-Shirt | Quilted Jacket | Flare Jeans | Leopard Sneakers

Shown Above Left: Sweater Dress | Denim Jacket | Leopard Belt | Saddle Bag | Ballet Flats

Shown Above Right: Denim Jacket | Vote T-Shirt | Leggings | Saddle Bag | Ballet Flats

Shown Above Left: Floral Dress (size medium) | Wool Coat | Ballet Flats

Shown Above Right: Floral Dress | Burgundy Bag | Knee High Boots

Shown Above Left: Cargo Jacket | Striped T-Shirt | Headband | Saddle Bag | Corduroys | Ankle Boots

Shown Above Right: Cargo Jacket | Striped T-Shirt | Floral Dress | Saddle Bag |Ankle Boots

Shown Above Left: Plaid Blazer (size 4) c/o | Sweater Dress | Burgundy Bag | Knee High Boots

Shown Above Right: Plaid Blazer | Cardigan | Flare Jeans | Burgundy Bag | Knee High Boots

Shown Above Left: Sweater | Saddle Bag | Denim Skirt | Leopard Sneakers

Shown Above Right: Quilted Jacket | Plaid Shirt | Denim Skirt | Leopard Sneakers

Shown Above Left: Plaid Blazer | Cardigan | Corduroys | Knee High Boots

Shown Above Right: Cardigan | Floral Dress | Leopard Belt | Knee High Boots

Shown Above Left: Denim Jacket | Stripe Tee | Leggings | Burgundy Bag | Ballet Flats

Shown Above Right: Quilted Jacket | Striped Tee | Leopard Belt | Denim Skirt | Knee High Boots

Shown Above Left: Wool Coat | Striped Tee | Silk Scarf | Flare Jeans | Ankle Boots

Shown Above Right: Wool Coat | Sweater | Corduroys | Knee High Boots



The other week, I switched my closet from summer to fall and felt so excited to pull out some of my older favorites to re-wear again. While I always love adding new pieces to my wardrobe, it’s important for me to appreciate what I already have and not fall into the trap of needed all new things each season. Then last week I noticed a post from Meghan of Wit & Whimsy (a blog I always love reading) sharing what she was buying for Fall plus the pieces already in her closet that she was excited to break out again. I loved the idea so much that I knew I wanted to do a similar post. Below – the pieces that I’ll be re-wearing from season’s past (and how you can get the look) along with what I’ve bought for Fall so far.


  • The striped sweater shown above that is truly just perfect. It has a boxy, slightly cropped fit (I sized down to a XS) and a great weight to it. I like it with a pair of high waisted jeans and loafers.
  • I actually bought this chocolate croc bucket bag way back in summer because I’d been looking for a classic brown bag for ages and this one went on sale. It’s back to full price, but honestly for the quality and timelessness – I think it’s worth it.
  • I’ve been thinking about buying this cardigan for TWO YEARS now. And I finally bit the bullet. It’s so luxe in person and because you can wear it frontwards or backwards I really think the styling options will be endless. Thinking of doing an IGTV styling video showing 5 ways to wear it?
  • Oppositely, this crewneck sweatshirt (I’m calling the color “pumpkin spice”) was an impulse buy, but it’s already proving to be a fall staple. And it’s on sale for less than $30.


  • This suede jacket was another higher price point item that I saved up for 4-5 years ago and based on how many times I’ve worn it – the cost per wear is pennies now. It looks effortless thrown on with everything from jeans and a tee to a pretty dress. This year’s version is still a close match.
  • These cropped wide leg jeans were a new addition last Fall and I love the way they’re slightly more polished than my regular denim. As an added bonus they serve to nicely show off a cute pair of shoes. This pair from the same brand looks like a very close match.
The Steele Maiden - 3 Must Have Coats for Fall Travel
  • A lightweight rain jacket and rain boots always come in handy. I love how this bright yellow one has a sort of classic fisherman feel. And you can’t go wrong with Hunter Boots.
  • I reach for this classic leather saddle bag all the time in the fall. It’s big enough to hold all of your essentials plus a book (which for me is actually essential) but doesn’t look bulky. This one is an almost identical match.
The Steele Maiden Fall Style - Talbots Silk Scarf Plaid Blazer
  • A classic plaid blazer is an absolute staple in my fall wardrobe. I got this maybe 2 years ago and I still wear it on average once a week this time of year. This and this are both similar options.
The Steele Maiden: Fall Floral Maxi with Old Navy
  • This floral midi dress is 2-3 years old at this point but I always find myself excited to wear it again. This could be dressed up with heels or layered with a sweater and boots for the weekend. This option looks to be a very similar version.
  • This pink corduroy blazer was an unexpected standout of my fall wardrobe last year. It’s definitely going to be a repeat offender in Zoom calls again this year. The brand is offering a really similar version this season here.




There’s something infinitely chic to me about brown croc print accessories – and I’m seeing them pop up everywhere this fall. I sadly don’t think I’m going to have all that many occasions to get dressed up this season, but even a bag like this one (a bit of a higher price point but I love it and know that I’ll be carrying it for years to come) dresses up a simple pair of jeans and sweater in a way that feels sophisticated and effortless. Below – my favorites that I’ve spotted around the internet.

10 Brown Croc Accessories for Fall:



In my mind it’s somewhere around June 15th. But in reality, this is the last weekend of August. This time of year always feels a little bittersweet to me, but perhaps never more so than this year. I mean, I never even made it to the beach.. how can summer be over?! And the looming uncertainty of what’s to come this winter has me shivering on a 90 degree day.

But, on the other hand – I truly love the feeling of fall and September always feels like a fresh start. So I’m trying my best to give in to the time warp that is 2020 and just lean into the excitement I feel over the change of seasons.

As it were – this outfit has a bit of a foot in each season. A floaty summer dress. A new bag that is sure to be a fall staple. In a couple of months time, I’ll pair this same dress with a cozy, oversized sweater and leather riding boots.

Until then – I’ll be doing my damnedest to soak up every last moment of summer. I hope you do the same.




I’m never one to wish away summer, but every year around mid-August I start to get the craving for Fall styles. Something about the promise of a new season, no? Below, the styles I have my eye on, that can be worn now and right on into fall.


  • This ‘Pretty Woman’-esque dress is calling my name and is on major sale right now (just $50!). No further explanation necessary.
  • I don’t have much occasion lately for statement earrings but these classic gold link earrings are perfect for instantly adding a touch of polish to your look. They’d be great for Zoom calls.
  • A timely vote t-shirt – all proceeds go to the ACLU.
  • I’ve been swooning over domed and signet rings lately to offset my daintier everyday pieces. This one is super affordable and can be engraved while this one is a bit pricier (around $200) but feels like a forever piece. And don’t get me started on this ‘croissant’ ring!
  • This plaid tie front blouse feels a little bit 1970s cool, a little bit British schoolgirl. Aka – my sweet spot.
  • I don’t see the need for face masks going away any time soon. I desperately need a couple more in my rotation and like these transitional floral prints.
  • The silk slip skirt is a trend that I didn’t immediately think was for me – but last year I picked up a black version and loved how versatile it was. I’d style this rust-hued one with a simple tee shirt now or a chunky sweater later.
  • I’ll be honest, my heels haven’t seen the light of day in quite some time. And I don’t know if fall is going to change that. Instead – I’m looking for cute flats for walking around town. These leopard sneakers are fun and these pretty gold ballet flats feel like they’re just begging to be taken to Paris someday.
  • Blame it on Taylor Swift’s ‘Cardigan‘ but all I want is a cozy knit sweater with a vintage feel. I think I’d wear this navy anchor version for years to come.
  • I, for one, am still not over headbands. This plaid one would look just as cute with a bathing suit as it would with a fall blazer.
  • If you’re in the market for a new purse this fall – might I suggest this classic option, in an impossibly chic ‘cappuccino‘ hue. I have a few bags from this brand and the quality and wearability far exceeds the cost.
  • If you’re not in the market for a new purse, one of my favorite ways to dress up an existing bag is by tying a fun scarf to the handle. The print on this one looks convincingly vintage and adds a nice pop of color to an otherwise neutral outfit.

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