I've said it once, and I'll say it again: Fall is the best season for getting dressed. It's the time of year when I can finally live in my cozy sweaters and my favorite fall boots 24/7. Excited as I may be, actually putting together a great fall outfit is tricky now that I'm out of practice. Oh—and a few of my fall essentials look a little drab after sitting in a box all summer. That's why I scoured the sale sections at J.Crew, Madewell, and Everlane to fill in the gaps in my collection and style some seriously chic (and affordable) outfits.
I developed nine editor-approved ensembles inspired by the oh-so-trendy street-style set. My looks include the best fall jackets and coats alongside jeans that tap into the season's must-have denim trends. These finds are versatile and made to be mixed and matched. Grab a slip dress from one outfit formula and style it with a V-neck sweater or button-down from another. This season is all about mastering the layered look, and these pieces will help you get it right.
Keep scrolling to shop my top fall looks from my favorite retailers. Each outfit will cost you less than $350, so you can look cute and stay on-budget.
A Blazer and Jeans
I always rely on my blazer-and-jeans outfit formula when I want to look put-together. Play with proportions with an oversized jacket, but keep things elevated underneath by opting for slim jeans and a white T-shirt.
Baggy Jeans and a Button-Down Shirt
Baggy jeans are everywhere this season. If you think the trend can’t look polished, think again—they look great when worn with wardrobe fundamentals like a tank top and an unbuttoned overshirt. It's an unfussy, classic outfit that works for transitional weather.
A Shirtdress and Loafers
A shirtdress is undeniably the best outfit for the office this fall. Pair it with some classic loafers, and you’ve got a fall work outfit that will never fail to impress your boss. If you want to add some shape, accessorize with a belt.
Black Monochrome
All-black outfits save me on mornings when I don't know what to wear (or when I'm running low on time). Maybe it's the New Yorker in me, but I find the result to be undeniably chic. I love pairing a leather blazer with a turtleneck for a cool-girl look. You can also play around with accessories for added texture or a pop of color (if you must).
A Pullover Sweater and Trousers
This outfit combination may be simple, but it's always so elegant. I recommend working with similar tones—like gray, one of fall's top trending colors—for a more cohesive finished look.
A Layered V-Neck Sweater and Denim Skirt
This outfit makes layering easy. Pair a V-neck sweater with a fresh white button-down shirt and a trendy maxi denim skirt for a mature take on your grade school uniform. Knee-high boots are an added bonus.
A Turtleneck and Midi Skirt
Yes, you can still wear your midi skirts in the fall. Swap out your usual white tee for a cashmere sweater like this one from Everlane for a cold-weather-ready look that relies on the basics.
A Trench Coat and Flats
On those fall days when you're rushing to get out the door, let your coat do the talking. A trench coat is a classic for a reason. No one has to know you're just wearing a few elevated basics—like a classic slip dress—underneath.
Barrel Jeans and a Striped Sweater
In a similar vein to baggy jeans, barrel jeans are the fashion crowd’s current denim fixation—just look at how often Katie Holmes has worn the barrel trend if you need proof.
