Summer to Fall Dressing
How I am taking tanks and shorts into cooler months and my latest (surprising) favorite pants.
August is basically here, and as per usual I am ready to start (lightly) thinking about what I’m wearing come fall. To start the season transition I always think about my current uniform and how I’ll evolve those pieces into something fall-appropriate. I’ll swap sleeveless for long sleeves, vests for cardigans, add a layer to light fabrics— you get the gist! Details below.
My Current Everyday Uniform Tweaked
This started as my everyday uniform I recently posted about: a sleeveless knit and long shorts. Now I'm just slightly evolving it. A T-shirt underneath the knit (I am very into this Scanlan Theodore knit tank- a good cut on the neck and shoulders), or swapping the sleeveless knit for a lightweight cardigan.

Styling Notes:
If you’re layering a T-shirt under a vest, I like when you can see a little of the neckline and pushing up or rolling the sleeves.
This very thin little cardigan is so cute. It’s lightweight with tiny buttons all the way up and a high neckline. I can wear it right now, but I’ll wear it into fall, too.
I’m wearing sandals here, but this and pretty much all of these outfits would work just as well with ballet flats if you live somewhere you want your feet covered for fall.
Summer Fabrics + Fall Layer
Also “how to wear a bomber right now.” I threw on a bomber jacket over all the lightweight fabrics I've been wearing all summer so it still feels summery and light but brings in a bit of fall.

This styling was inspired by this and this Phoebe Philo bomber outfits I’ve been eyeing.
I think a bomber with jeans is most people’s default, I prefer it with softer fabrics. It feels a little more directional.
I’ve been wearing a lot of fluid pants, cotton tanks, and silky button-downs, which work really well with the bomber over top.
I love these CO pants to wear with a jacket; they sit not too high and not too low. Very effortless fit.
Balloon Pants
I’m surprising myself by saying this, but these balloon pants have in heavy rotation lately. They just might be the hero of this post. They are fluid, effortless and make you feel great. The definition of easy.

I never thought I was going to be a balloon pant person, but here I am.
These midnight navy ones from Scanlan Theodore are flattering, incredibly comfortable, and just easy to wear now and also cooler weather with a sweater.
I love the relaxed ease of the matching set. Pair it with lightweight bag and strappy sandals.
See above in the bomber section for how to style with a jacket and ballet flats.
My Other Everyday Uniform Tweaked
I’ve really been leaning on drawstring and cinch waist pants all summer with simple cotton tanks. For fall, my plan is to pair them with a knit polo (this one is perfect) instead. It still carries that relaxed energy of summer but is appropriate for fall.

Styling Notes:
Accessories are an easy way to make an outfit read fall, and I think adding a fall bag with a suede or dark leather texture is an easier solve than a fall shoe.
When it comes to a drawstring waist, style with something that hits right at the top of the pant. The Elastic waist is best with something that has a nice hang and covers the waistband. This sweater works both ways.
Métier Callas bag is my new lux tote. The leather is so good and substantial, dark brown and suede read very fall.
White Sneaker
Whatever you do, do not break these in without socks or you will regret it. I still love them. For summer, I’ve been wearing them with shorts and socks or cropped pants and socks. For fall, I like them with really dark, clean straight-leg jean and something simple like a button-down or sweater.
Next post, a deeper dive into how to wear socks with sneakers.
See you then,
xo
ali







You have no idea how helpful this is.
i'm so excited for the next post on sneakers. more on styling sneakers, please—different kinds, white, black, colors, etc. thank you <333