We know that Fall shopping [1] can feel like a drag — you have to think about which layers you might be missing and how to style them [2]. Why can't updating your wardrobe for the new season just be easy? Like, Summer-slip-dress-easy? Your wish has been granted. Let us take you under our wing and show you the one-and-done pieces that will go for miles and miles — maybe even beyond Winter. Think of the clothes ahead as armor you can work in with so many different things you already own [3]. Trust us, they're all worth the investment.
J.Crew Sweatshirt and Skirt
An easy but striking monochrome look comes by way of this J.Crew Tie-Sleeve Sweatshirt [5] ($53) and matching Wool Flannel Ruffle Skirt [6] ($98).
Zara Contrasting Velvet Ankle Boot
A durable sock boot will go with everything, like this Zara Contrasting Velvet Pair [7] ($50).
Blank Denim Jacket
Find a live-in denim topper you can really play up and personalize, like this Blank Denim Jacket [8] ($128).
Urban Outfitters Koi Bandana
This Urban Outfitters Koi Scene Bandana [9] ($8) is the moody silk scarf you can tie onto everything, from your sleeve to your purse.
Zara Striped Set
Invest in a coordinated set that's secretly comfortable, like the Zara Striped Blazer [10] ($119) and Pyjama Style Trousers [11] ($70).
Club Monaco Tatelyn Bow Slide
Add a luxurious flat in an interesting silhouette to your rotation. This Club Monaco Tatelyn Bow Slide [12] ($349) makes for the perfect option.
ASOS Balloon-Fit Chino
You can dress up these ASOS Balloon-Fit Wide-Leg Chino Pants [13] ($48) or pair them with sneakers and dress them down.
Diane von Furstenberg Long-Sleeve Maxi Shirtdress
Play to your inner boho queen all season long in the Diane von Furstenberg Long-Sleeve Maxi Shirtdress [14] ($598).
Adidas by Stella McCartney Ultraboost Sneakers
The Adidas by Stella McCartney Ultraboost X Sneakers [15] ($250) play to the trends and would look just as good with leggings as they would with denim and a ruffled blouse.
Brixton Fiddler Cap
If there's one hat everyone will be wearing to hide a bad hair day, it's the newsboy cap. This Brixton Fiddler Cap [16] ($47) fits the bill.
Burberry Unisex Gabardine Trench Jacket
Invest in a neutral layering piece like the Burberry Unisex Tropical Gabardine Trench Jacket [17] ($1,595).
Club Monaco Chavelle Faux Leather Skirt
You'll never want to take off the Club Monaco Chavelle Faux Leather Skirt [18] ($150), and it will go with so many tops that you really won't need to.
Forever 21 Ruffle Flounce Shirt
Find a little white blouse with something extra, like the Forever 21 FOREVER 21+ Plus-Size Ruffle Flounce Shirt [19] ($35).
Etoile Isabel Marant Check Skirt
What says "Fall" more than a touch of plaid? The side bow on the Etoile Isabel Marant knotted check skirt [20] ($250) will lend your look '80s vibes [21].
Tibi Jean Leather Boots
Everyone will be wearing little white boots come Fall, but with the Tibi Jean Leather Boots [22] ($595), you'll be in the silhouette of the season.
Zara Fringed Jacket
Won't you want a cozy sweater to throw over everything? Mix prints in the Zara Fringed Jacket [23] ($100).
Slink Jeans Step Hem Skinny Jeans
Your skinny denim gets an update at the heel with the Plus-Size Women's Slink Step Hem Skinny Jeans [24] ($98).
Reformation Sorrenti Pant
Find a pair of movable printed trousers you can pair with your favorite band tees. Does the Reformation Sorrenti Pant [25] ($178) work for you?
Coach Western Aviator Jacket
If this Coach Western Aviator Jacket [26] ($2,650) was in our closet, we don't think we'd slip into a different coat all season.
Aquazzura Floral Booties
Booties with appliqué and jacquard will score you all the compliments. Start with the Aquazzura Floral Embroidered Block Booties [27] ($825), which you can wear through Winter and Spring too.
Alexander Wang Dry French Terry Jumpsuit
We'll all still be wearing white come Fall, so find something striking with sleeves like the Alexander Wang Dry French Terry Long-Sleeve Tie-Back Jumpsuit [28] ($450).
Jeffrey Campbell Gamora Thigh-High Boot
We promise you that "legging boots" will be everywhere [29], so find something with height like the Jeffrey Campbell Women's Gamora Thigh-High Boot [30] ($190).
Sjyp Cutoff Denim Overalls
If you're going to add more denim to your rotation, make sure it's as extraordinary as the Sjyp Cutoff Denim Overalls [31] ($430), which you can wear with everything, letting the distressed hem peek out from under cocoon coats.
ASOS Wrap-Front Midi Dress
You can't go wrong when you add an LBD like this ASOS Wrap-Front Midi Dress With Frill Detail [32] ($60) to your wardrobe.
Munn Green Lace Long Dress
Why not add another layering piece to your wardrobe? You can throw this Munn Green Lace Long Dress [33] ($574) on over jeans and complete with a blazer and platform shoes.