The 13 Transitional Pieces You'll Wear Most Between Now and November

As we get swept up in a barrage of Pre-Fall and Fall new arrival content, it’s incredibly tempting to feel like we need to do a complete overhaul of our wardrobe, but for most women, a gentle transition into Fall is all you need! There are so many pieces that are perfect to wear now in August and become beautiful layering pieces all the way through November.

A “gentle transition” means subtle changes in footwear (rather than making the jump from flip flops to boots, we may be swapping in suede wrap sandals and ballet flats), accessories (think moving from raffia to suede), color (stark white to ivory as an example) and texture (introducing cashmere, for instance).

This year, I’m doubling down on some of my favorite staples (I’ll also give myself permission to pick up a few new things because it’s so fun…I just am not going to give into the pressure to need to pick up a ton of new stuff).

Here are the pieces I wear the most from August through November. Hopefully you have many of these in your closet but if you need to pick something up, the good news is, it should get plenty of wear!

Cashmere Tee: Just a little too hot for peak summer, but as soon as the humidity breaks I pull out a cashmere tee. I just love how soft and lightweight it is. Looks great with a skirt or jeans and it’s so chic under a blazer or trench in the Fall. I’d start with this (in ivory grey and navy) for under $50!

Cotton Sweater: A great cotton sweater is good for at least three seasons and maybe all year depending how cold it gets in winter. In August I’ll usually throw over my shoulders, but I’ll also wear it on a windy beach day or for drinks on a chilly night. When things get a little colder in October and November, this will be a hero base layer before I switch to wool and cashmere. My three favorite cotton crewneck sweaters are this, this and this. If you prefer a rollneck, I love this and this.

This Neutral Skirt: I’m being really specific here on purpose. There is something about this skirt that is particularly perfect for the summer to Fall transition. It’s fun and flowy but somehow structured enough to easily dress up for church or work too. It truly works with everything from tee shirts and tanks to blouses and sweaters, sandals to boots.

Wrap Sandals: If there’s one piece I get the most pushback on depending on where people live and their temperature preferences, it’s footwear. If wearing a sandal late into Fall isn’t for you, that’s totally fine, but I tend to wear mine as late as I possibly can (with shorts, skirts and dresses in August and jeans or pants in the Fall)! I do tend to transition from a more traditional sandal to a suede wrap sandal (my favorite has low inventory but this is a great alt). I’m also loving these fisherman sandals so much right now.

A Classic Blazer: Probably the biggest workhorse for an in office look. It’s just so versatile and timeless. Throw on over a dress, blouse, button down, white tee or sweater. So many options! My favorite is this (in navy or herringbone) because of the perfect boxy silhouette and I’m loving the gold buttons I’m seeing more and more of.

A Great Button Down (this or this): Such a great beach cover up and the perfect piece to wear into the office with jeans for a thoughtful business casual look. Love this look with a pair of cap toe ballet flats and a neutral leather bucket bag. Easy to throw on a blazer if things get chilly! Silly expensive but one of my favorite all-time favorite shirts is this striped button-down.

Straight Leg Jeans: Jeans will absolutely be the most worn piece on this list so it’s super important to get it right. For a summer to Fall transition, focus on a medium wash. I like stiff premium denim because it looks the most pulled together on the days I want to dress them up a bit (harder to do with looser fitting jeans). These are my all time favorite jeans. For a premium feel for less, you can’t beat Levi’s in a new wash perfect for Fall. If you prefer a little stretch, these are my top pick. If you prefer a barrel shape, these are so great.

Pull on Pants: I love black or olive green here. Black are the most versatile (there are hundreds of outfits that are easy to create with a great pair of black pants as a base layer) but there’s something about green that works so well with a white tee and baseball cap in summer but also transitions to Fall colors beautifully when it’s time to throw on a sweater.

A Cardigan: Maybe one of the most obvious transition pieces…Is it as simple as unbuttoned in summer and buttoned in Fall? Maybe not quite, but this cashmere cardigan has pretty much ruined me (it’s that good). I wear it with denim or white jean shorts in the summer and pants all Fall. Such a great find! For another great option for a little less, this cotton cardigan and this t-shirt cardigan are also really, really good if you live in a warmer climate.

A Throw On and Go Dress: Wear on its own with some statement jewelry and a belt in August and throw on a beautiful cashmere sweater or blazer come November. A simple black or white dress allows you to be creative.

Ballet Flats: A neutral or cap toe (this or this) ballet flat works so well for skirts and dresses in August and jeans or pants in October. In just a few short weeks, I’ll start to introduce suede shoes into my wardrobe and I couldn’t be more excited to start wearing these gain!

A Suede Bag: One the easy ways to gently transition to Fall is to swap out raffia for suede. I love a suede bucket bag or shopper tote for all my Fall errands when I’m out and about.

A great pair of sweatpants: I love a cozy pair of sweats for coffee runs or Sunday cozies. These are my most worn for years running, but I also love a striped option to add a little interest. Just throw on a long sleeve tee, a trench and a baseball cap for a casual but chic look.

A great transitional piece can be worn on its own or layered with other pieces when the weather turns. All it takes is a little creative styling.

I hope the visuals and descriptions help show how to make your wardrobe basics stretch a little farther this year. Everything is linked here.

As always let me know if you have any questions!

xx, Meg