It’s finally fall, ya’ll! Even if it’s 80 degrees outside, at this point, I’m wholeheartedly committed to dressing for the season. The transition from summer to fall is arguably one of the more exciting times for fashion, as it opens up a world of possibilities to mix and match styles.
For me, this time of year is all about creative layering, where lightweight summer pieces can be paired with cozy fall staples. I love creating unique outfits that capture the spirit of both seasons.
8 Fall Outfit Ideas For September
As we transition into fall, I’ve been leaning heavily on vests, striped tops and wide-leg denim to build some cute early fall outfits. I’m currently in the middle of a closet clean-out and in the process I re-discovered some of my favorite pieces from seasons passed, like my vintage camo pants, my black straight leg Levi jeans and my Easy Street Tunic sweater from Free People.
I had so much fun pairing some of my new closet essentials like my Citizen of Humanity’s Alya cuffed jeans and my Reformation denim mini dress with pieces I already owned. Here are 8 outfit ideas to wear as we welcome fall with open arms.
1. Bright Stripes + Wide-Leg Dark Wash Mother Jeans
An unexpected outfit combo that I ended up loving: my bright orange striped top from Mango paired perfectly with the dark wash Mother jeans I’ve been wearing non-stop lately. To complete the look I added in my woven handbag from Anthropologie and my Adidas Sambas, of course.
Top (M) | Jeans (29) | Sambas (7.5) | Bag
NOTES: These high-waisted Mother jeans are made from 41% recycled cotton, 41% lyocell, 18% cotton, and although the fabric is lightweight and breathable there isn’t much stretch and I found that they run a little small, so order one size up.
2. Vintage Camo Pants + Off-Shoulder Sweater + Adidas Sambas
I completely forgot about these vintage Camo pants that I bought on Etsy a few years ago and only just rediscovered them while cleaning out my closet. I have a feeling I will be wearing them all fall. I contrasted the ‘rough and tough’ casual vibe of my camo pants with a slightly flirty off-shoulder sweater.
Sweater (M) | Similar Pants | Sambas
NOTES: I love this Treasure & Bond off-shoulder sweater so much that I have it in four different colors now. It’s been a wardrobe staple in my closet for the past six or seven years. It’s honestly one of my most worn sweaters of all time and the best part about it, besides how comfortable it is, is the affordable price point.
3. Striped Tee + Citizens of Humanity Cuffed Jeans + Adidas Sambas
This super fun Endless Rose striped top caught my attention immediately. I love tops like this one, that are classic and timeless but with a lil’ twist. The unique sleeves add the perfect amount of interest to this look.
Shirt (M) | Jeans (28) | Sambas (7.5) | Belt Bag
NOTES: These Citizens of Humanity Ayla jeans are my most worn jeans as of late. I love how soft and comfortable the fabric is. These jeans definitely run large though. I am usually a 28 or 29 in denim and even the size 28 were a tad too large on me.
4. Denim Vest + Black Straight Leg Jeans + Clarks Wallabees
I finally bought myself a pair of the Clarks Wallabee’s that I’ve been wanting for awhile now. I was a little bit worried that I wouldn’t know how to style them but thankfully my trusty black straight leg Levi’s came in and saved the day. I think I’ll be pairing my Clark boots with more straight-leg jeans all fall long.
Denim Vest (8) | Jeans (29) | Shoes (8)
NOTES: I’ve worn these Levi’s so much over the years that they got a hole in the knee that I had to patch myself (that’s how much I love them). Also, my Madewell vest keeps selling out but keep checking back as Madewell is usually pretty good at restocking their most popular pieces.
5. White Turtleneck + Reformation Denim Mini Dress + Moto Boots
I’ve written about my love for this Reformation denim dress already in a previous post but, surprise, surprise, I’m still wearing it and loving it. Thankfully, this dress looks super cute with a turtleneck layered underneath and it will make the perfect transition to fall.
Turtleneck (M) | Dress (8) | Boots (8)
NOTES: I ordered a size 8 in the dress because it looked short on the model, but it’s a little bit too loose and I plan on exchanging it for a size six, so it runs a little bit large. I also went up half a size in the boots because I have wider calves and the size 8 fit perfectly.
6. Free People Sweater Vest + Black Straight Leg Jeans + Clark Wallabees
I knew as soon as I tried on this Free People sweater vest during the Nordstrom Sale that it would come in clutch this fall and so far, it has not disappointed. It’s the perfect length as well: not too cropped and not too long, so that it shows off my waistline without also showing off my belly-button. It’s super soft and comfortable as well.
Sweater Vest (M) | Jeans (29) | Boots (8)
NOTES: As with most Levi jeans, these black straight jeans run small. I ordered one size up. I also ordered 1/2 size up in the boots because I plan on wearing chunky socks with them this winter. If you’re on the fence about Clark’s Wallabees, do it! They are some of the most comfortable shoes I’ve put on my feet.
7. An Oversized Sweater + Lace Floral Skirt + Moto Boots
My millennial heart is so happy that lace-trim skirts are coming back into style. As a college student in Los Angeles in the early 00’s, I pretty much exclusively wore thrifted lace slip skirts and dresses. I picked up this lace skirt during the Nordstrom Anniversary Sale and it just so happens to be on sale again for under $40.
Sweater (M) | Skirt (6) | Boots (8) | Similar Bag
NOTES: Can we just take a moment to praise my Free People Easy Street Tunic sweater? I’ve had this sweater for YEARS now and when fall arrives, you can be sure I’m wearing this sweater (or the cropped version I also own) at least once a week. It really is THAT good.
8. Tie-Front Top + Agolde Straight Leg Jeans + Mesh Ballet Flats
So, I pulled out my old Agolde straight-leg jeans because I remember not too long ago that I exclusively wore these jeans and nothing else. Now that I’ve gotten so used to wearing barrel and wide-leg jeans it was a little bit of a shock to see myself in such a form-fitting pair of jeans.
Top (M) | Jeans (29) | Ballet Flats (7.5)
NOTES: Honestly though, I am kinda digging this silhouette and these jeans are a great option for when you want to show off interesting footwear. These jeans run small so order one size up.
Hope you’re having a fabulous fall! Until next time,
xo, Jess ( My Instagram | More of My Posts )
