In Chicago, September has felt like a continuation of August – a streak of sunny days in the low 80’s.  I’m not complaining!  However, I knew I needed to update my fall wardrobe – and the weather was not putting me in the mood.  Like all strong women, I persevered and went shopping anyway.  I have found some great pieces that will update my wardrobe for fall – and beyond.

Where to Begin Your Fall Wardrobe Refresh

Do not be daunted. As with anything, if you break it down it will become more manageable. To start, consider these three things and make a running list of must have, nice-to-have and bonus items that will build an updated fall wardrobe.

Shop Your Closet

The first place to start is to take inventory of what you have. What do you really like? Which items could be freshened up with a different sweater or belt? This will be the foundation on which you can layer in some more on-trend pieces to build your fall wardrobe.

Consider Your Lifestyle

As much as I love shopping and clothes, I am no longer going into an office everyday where I need professional and stylish outfits.  I am now consulting, doing more Zoom meetings with the occasional lunch and in-person meeting.  So, my focus is on pieces that I can pair with my existing wardrobe and have the flexibility to dress up or down.

Shop the Trends

I try not to hop on every trend, but rather consider them and think about how I can adapt them to my style (as I wrote about in this post).  For quite some time, I’ve been seeing some trends that I wanted to test out.  I jumped on the barrel jean bandwagon last year (see this post)– and they are clearly not going away.  I love the longer, baggier blazer trend and am seeing lots of brown and burgundy which could freshen up my fall wardrobe.

Building My Fall Wardrobe Update

Blazers

I have some gorgeous Theory blazers that I consider investment pieces.  They are nearly a decade old and still look, and fit, great.  That said, they don’t have the casual ease of today’s look.  Back in May, I went in search of a longer, more loose-fitting, casual black blazer that I could dress up or down.  I purchased this one at Nordstrom and never took the tags off, not sure I’d keep it.  Until now–I pulled it out and it’s still perfect for the fall wardrobe reset. I also got this double-breasted blazer at Evereve.

Woman trying on a black blazer in her quest to do a fall wardrobe refresh.
Nordstrom black blazer
[BlankNYC] brown & black plaid blazer
from Evereve

The Trench

I love a trench coat, but don’t really have a need for a full-length trench coat.  After seeing this cropped trench at Zara,  I thought it could do double-duty as both outerwear and a jacket/blazer.  Ideally, I like to try things on at Zara, to get the size right.  And, things sell out really fast there.  So, I was thrilled to find this one.  I went with a size small, which is still roomy enough for layering over sweaters as we get deeper into fall.

Zara, Short Cropped Trench

Color

Brown

My love for neutral shoes, boots and bags is well documented .  But this year I’m really gravitating toward the deep brown tones.  I quickly found that not all browns are created equal.  And, I don’t like the browns that are lighter or have red undertones.  For my fall wardrobe, I like the very deep, chocolate brown – think dark chocolate vs. milk chocolate.   

Burgundy

Another trend for fall is lots of burgundy.  I’ve seen it declared “Fall’s biggest color trend” and it is everywhere.  I have a complicated relationship with burgundy (or “maroon” as it was known when I was growing up).  My mother LOVED the color and bought my sister and I multiple maroon outfits. 

She believed that you should “dress” for any occasion –including grade school.  Fun fact: I could not wear jeans to school until my sophomore year of high school.  Anyway, the only time I ever skipped school was one day in 8th grade.  That morning, I met my best friend at the corner of her block for our daily walk to school.  I had worn this pair of maroon check pants that were “floods”.  I was mortified and cried to her that I could not be seen in these pants.  We spent the entire day hiding out at her house, having great fun and getting into just a little trouble.

I decided to not let my 8th grade memories keep me from this fall wardrobe trend.  So, I will dip my toe into burgundy with some accent pieces.  

Banana Republic, Midweight Cropped Cashmere Sweater

Suede

I’m seeing gorgeous suede jackets, boots and bags this season.  Also, as I looked at the browns, there is a richness that comes through in suede vs. leather.  So, I went with brown suede booties and a bag. 

Banana Republic, Italian Suede Ankle Boot
Madewell, “The Shopper” tote in brown suede

Dark Denim

Denim has emerged as the ultimate versatile player.  And, I love that we’re seeing more variety in denim beyond the distressed, raw hem.  I still love the juxtaposition of distressed jeans with a nice blazer and boots – but am excited about the clean look of dark wash denim.  It feels fresh and elevated.

Woman trying on BDG jeans at Urban Outfitters.
Urban Outfitters, BDG Kayla Low Rider jean
Woman trying on Zara cropped straight flare to add to her fall wardrobe.
Zara, Cropped Straight Flare

Barrel, Barrel Everywhere

I was an early adopter of the barrel jeans trend as I wrote about in this post.  And, I love that we’re now seeing the barrel, or horseshoe, silhouette beyond jeans and in other pants and trousers.  Last year, I was asking myself if you can have too many barrel pants – this year the answer is ABSOLUTLY NOT! So, the Barrel Bandwagon continues into pants and trousers.  I’m all in!

Woman trying on Citizens of Humanity Marcella barrel cargo pant to add to her fall wardrobe refresh.
Woman in the dressing room at COS, trying on a pair of wool-blend, barrel shaped dress pants to add to her fall wardrobe.
Left: Citizens of Humanity, Marcella in size 8. Above, COS wool blend pleated, cropped barrel pants. I tried these on for size (8) but ordered them in black.

Chunky Glasses

Woman trying on chunky oversized frames by Prada.

Most days I wear contacts so that I can wear sunglasses.  But in the winter, I do wear my glasses more often.  And I wear them as a statement accessory.  Because I wear them so infrequently, I only buy new glasses every few years.  And while chunky glasses are not a new trend –I decided to splurge this year.  After trying pairs at Warby Parker, I landed on these oversized chunky Prada frames.  I usually buy tortoise shell, but this year, went a little bold, with the straight black frames.  This is the ultimate accessory to round out my fall wardrobe.

My Fall Wardrobe is Ready!

Now that I’ve documented it all here, it was a pretty big reset of my fall wardrobe. However, I think all these items are on-trend, without being too trendy. So, I feel pretty good that everything is going to look current this year and will have solid wardrobe rotation for years to come. 

WETSU! WETSU!

XO  JT

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