1. Madewell Perfect Vintage Wide-Leg Jeans

I’m loving the return of the subtle wide-leg jean this season and this pair from Madewell look perfect for year-round wear thanks to the light but not too-light wash.

I generally size down in Madewell denim. 

2. Reformation Silk Trousers

I wear trousers year round these days and am very into lightweight silk ones for dressier occasions at the moment. You could pair with a chunkier knit, a short sleeve sweater, or a tank with a jacket layered on top. I own this pair in a M and another color is on my Fall Wish List.

If silk isn’t your style, these are one of my go-to pairs!

3. J.Crew Relaxed Emilie Lady Jacket

The iconic J.Crew striped lady jacket is back in a more relaxed fit! This lightweight sweater is super versatile…style over dresses, with jeans, or a tailored shirt when the weather is still warm.

4. Varley Rib Knit Midi Dress

I love a short-sleeve knit dress for transitional dressing, and this midi dress from Varley is in the perfect Fall color. For a more casual look pair with sneakers, and as the weather cools you can layer a jacket and style with tall boots.

5. Abercrombie Short-Sleeve Cardigan

When it’s still too warm for a full cardigan, this short sleeve lady jacket is the perfect option. I think the contrast trim and gold buttons really elevate this $60 sweater.

6. Adidas Sambas

I’m loving the sporty sneaker trend, especially this white and beige colorway I recently purchased myself. Pair these with everything from dresses, to skirts, to denim year round.

7. Madewell Gold Belt

Run, don’t walk, to scoop up this designer looking belt for a fraction of the price. It seems so minor, but a belt adds such a nice finishing touch to an outfit. I personally bought this belt and it is beautiful.

8. Sam Edelman Cap Toe Ballet Flats

Ballet flats are worn by me year round but always get more air time come Fall. This is a good get the designer look for less pair.

9. J.Crew Denim Lady Jacket

I have a denim lady jacket very similar to this and I always get so many compliments! It’s the perfect in-between layer to throw over a dress or pair with a skirt.

10. J.Crew Cotton Rollneck Sweater

A classic rollneck sweater in 100% cotton is a wardrobe staple for me. I love this ivory color, but it also comes in stripes.

11. Mango Crossbody Bag

Mango has such a great selection of affordable bags. This timeless crossbody also comes in black if that’s more your speed.

12. J.Crew Cashmere Tee

A cashmere tee is essential for transitional dressing! It’s the perfect bridge between Summer and Fall and can be styled with denim, shorts, or trousers. This is a piece you can reach for well into Fall and Winter.

13. Madewell Baseball Cap

My ball cap collection has grown significantly the last two years and I love styling them with favorite sweaters and denim shorts alongside blazers and jeans, too. I think the leather strap detail make this feel more elevated than your average baseball cap.

14. Madewell Essential Bucket Tote

This one looks like The Row but is a fraction of the cost coming in at under $200. I love how chic it is and the chocolate brown color is just gorgeous. 

15. Everlane Quilted Liner Jacket

This super chic lightweight jacket is perfect for early Fall days when you don’t need a full Winter coat. It also comes in olive and brown if you want to switch things up. 

Fall Transition Outfits

Need a little Fall transition outfit inspo? I’ve got you covered with outfits that incorporate both Summer and Fall components to keep you looking stylish, but still weather appropriate for those in-between days.

Lady jacket and jeans

Pair a lightweight lady jacket with a classic pair of jeans and sneakers. I love adding a baseball cap for an off-duty chic look.