Transitional dressing isn’t exactly what you’d call easy, what with weather forecasts all over the map and all. Over or under dressing practically becomes a daily reality. And to make matters even more complicated, this year, that awkward in-between period just so happens to come at a time when Mercury is in retrograde — don’t even tell us that this is a coincidence. But girl, you don’t have to surrender yourself to a daily sartorial tragedy (life’s too short to suffer that many wardrobe conundrums). Armed with a few anytime-appropriate pieces (and these Insta-babe fall looks), ranging from It-girl-approved shoes to swingy midi skirts and badass bomber jackets, you can flawlessly transition into the new season sans problems. Scroll on for 25 trend-right pieces that make it all possible.
1. Zara Shiny Pleated Skirt ($40): Snuggly sweaters and ankle boots are practical picks for fall, but every capsule wardrobe needs at least one statement-making option on standby. Enter the twirl-worthy pleated skirt that will shake up your desk-to-dinner routine in true It girl-approved fashion. Rock it by day with a flirty ruffle-neck blouse and RN Mary Janes, then sass things up once the sun sets with embellished pumps, a strappy cami and badass leather jacket. #bombshell
2. Pixie Market High Collar Sleeve Tie Stripe Top ($109): Step aside, basic Breton stripes! Tried-and-true tees will always have a place of prestige in your wardrobe, but sometimes you just need a piece with a little more pizzazz — and this tie-embellished beauty is it. It’s a shoo-in for all those end-of-summer soirees on your iCal (just add lace-up sandals and a button-front skirt), plus it’ll keep your style feeling fun and fresh in the new season, where heavy knits rule supreme. Try layering it over a roll-neck top, cropped jeans and ankle boots FTW.
3. J.Crew Italian Silk Square Scarf in Vibrant Paisley ($50): At this point, donning an oversized scarf might be a little too much, but this elegant silk stunner couldn’t be more on cue. Wrap it around your neck or tie it onto a favorite handbag for a pop of lively color and panache.
4. 8 Neoprene Mesh and Faux Leather Jacket ($229): You lived in your trusty denim jacket all summer long, and it might kinda sorta be time to retire it to the back of the closet. Swap it out for this season’s go-to athleisure-inspired topper — the bomber jacket — that’s about to become your new hero piece in disguise. Whether you wear it over a flirty maxi dress and pumps or style it alongside a breezy boyfriend jean and tee combo, it’ll never disappoint.
5. Madewell Cali Denim-Boot Jeans in Donovan Wash ($128): Who doesn’t love a good pair of denim with endless now-and-later appeal? These mini flares are just what the stylist ordered with their cropped, high-rise silhouette that’s perfect for showing off a killer pair of kicks (we’re looking at you, fur-trimmed loafers). Toss them on with an oversized button-down and a bright menswear-inspired coat for an afternoon of running errands.
6. Equipment Layla Floral-Print Washed-Silk Camisoles ($120): You simply can’t go wrong with a silk camisole, especially one this DDG. Wear it alone with a metallic midi and ankle-strap sandals for after-hours shenanigans with the girls, or layer it under a long cable knit cardigan, Oxfords and treggings for off-duty dressing at its best.
7. Urban Outfitters Iman Loafer ($69): ICYMI: Loafers are officially a legit thing, and if you’re looking to take your err’day style to all new Insta-babe heights, they’re the one add-on you’ll definitely need in your arsenal. Avoid an overly preppy aesthetic by teaming them with don’t-mess essentials, like raw-edge denim, biker jackets and sleek, modern baubles.
8. & Other Stories Wool-Blend Cardigan ($125): Be it a cool summer night or an afternoon excursion to the orchard, this oversized cardi has you covered. Instead of packing up your favorite summer pieces prematurely, simply toss this ultra cozy number on top of summery sundresses, swishy skirts and strappy tanks to effortlessly usher duds into the new season.
9. Topshop Striped Tie-Up Body ($35): Never underestimate the power of a good basic. Bodysuits have ridden into the mainstream on the waves of the ’70s and ’90s fevers currently running through the industry, and we couldn’t be happier about it. The throw-on-and-go piece partners perfectly with almost every item in your closet, which makes it a frontrunner for wardrobe MVP. Scoop up this sassy tie-front style and proceed to pair with high-waisted jeans and a choker for an #OOTD that’s as cozy as it is chic.
10. Free People Love Is Blind Aviator ($25): A chic pair of shades never goes out of style, which is good news for both your #OOTD game and your wallet. Make those dwindling daylight hours count with these crossbar beauties and a pair of hot steppers that are equal parts OMG-worthy and effortless.
11. Mango Flecked Jersey Dress ($50): Whatever the season, there are certain capsule wardrobe must-haves you’ll inevitably reach for time and time again — and this jersey midi dress is one of them. It boasts the kind of one-and-done appeal every girl-on-the-go needs in her wardrobe, plus the soft jersey fabric will keep you comfy while you crunch numbers and run around town. Fake it ’til you make it with a statement choker, sleek chignon and platform loafers.
12. Wilfred Palmier Sweater ($125): The be-all end-all of transitional dressing? A sleeveless sweater that does it all. Pair this bold blue number with tailored trousers and fancy flats now, then layer it up with a bell-sleeved button-down and sophisticated joggers for a foolproof athleisure look later.
13. Dannijo Saturn Earrings ($220): Found it: The pair of geometric earrings that will refresh even the most blasé basic when your signature hoops start to feel meh. Between their shimmery crystals and intergalactic edge, all that’s missing is a metallic smokey eye for a daytime look that’s straight-up out of this world.
14. Rag & Bone Harris Printed Silk-Twill Dress ($248): Good news, ’90s babes: The slip dress is sticking around for fall, so you can keep those throwback vibes alive long after the warm weather has come and gone. The key to pulling it off post-Labor Day? Playing the layering game. Pop it on over a turtleneck tee and rock goddess boots for a getup that will slay from the streets to the office (and beyond).
15. Whistles Tie Detail Long Sleeve T-Shirt ($95): Minimalist enthusiasts, prepare to swoon hard for this updated long sleeve tee. With its simple silhouette and dramatic tie detailing, it’s the hero piece you didn’t know existed — until now. The fuss-free styling makes it prime for lazy afternoons curled up with a cup of tea and your latest read, but best believe it can hold it down on a night out too — just add a leather mini and a sassy statement clutch.
16. Zara Finely Pleated Printed Dress ($70): Introducing the sweet swing dress that makes achieving a model-off-duty look an effortless exercise. Everything from the free-wheelin’ fit to the ditsy floral print will make you want to adopt a grunge-era aesthetic this season. Pair it with combat boots, a leather backpack and an oversized denim jacket.
17. Warehouse Suedette Biker Jacket ($105): Just when you thought you’d perfected your GNO routine, this tough girl jacket steps onto the scene. Don’t even pretend like that plum-colored suede isn’t downright dreamy. Style with a slinky slip dress for a ‘90s-inspired ensemble that would make Kate Moss proud.
18. Vans Sk8-Hi Slim Sneaker ($60): Fresher than what?! Take your sneakers beyond the boundaries of off-duty dressing this season by taking notes from the street style elite. Team a pair of high tops or statement sneaks with floaty skirts, feminine frocks and tailored coats for an on-the-clock remix that strikes the right balance of sophisticated and downtown chic.
19. H&M Denim Skirt ($30): Say hello to the wardrobe workhorse you’ll be reaching for on the regular. Be it a buzzworthy gig or bowling with the girls, toss this zip-front skirt on with a bomber jacket and platform sandals (shimmery socks highly encouraged) for a laid-back late-night uniform that doesn’t mess around.
20. Lucky Star Jewels Suede Bolo Necklace ($48): Sure, statement chokers might be en vogue, but they just don’t jibe with your pared-down approach to dressing. Embrace the throwback trend without venturing out of your comfort zone with this subtle suede bolo that would look just as ah-mazing with a t-shirt and jeans as it would with a pinafore dress and peasant blouse.
21. Warehouse Popper Side Trouser ($98): WTF factor aside, track pants — and we’re not talking Jenna Lyons-approved silk joggers — are officially in, whether you’re ready for the blast-from-the-past trend or not. Tap into your inner Man Repeller and glam ‘em up with a boyfriend button-down, embroidered shacket and metallic steppers for an unexpected twist on the standard suit.
22. Charles & Keith Saddlebag ($59): Fall might have you bummin’, but there’s one thing that just might get you pumped about the cool weather season: this burgundy saddlebag that can be described as none other than straight-up #goals. Whether you’re chillin’ at the bar or brunching with the besties, take this boldly buckled bag along for the ride. The subtle throwback feel is the ultimate complement to a denim midi and knit bell-sleeved blouse.
23. J.Crew Cotton Shirt ($90): If white collared shirts aren’t your thing, all bets are on that you’ll fall head over heels for this military-esque topper. Play it cool by tucking it into leather joggers for an easy ensemble that can pull a little double duty.
24. Mango Pockets Cropped Jumpsuit ($80): Dancing divas and Insta-babes can agree — a streamlined jumpsuit is the key to an elevated after-hours look that requires zero effort. Don’t say we didn’t warn you: This cool-girl culotte style will have you craving a wild night out on the town with your crew. The only thing missing? A bold red pout and moto jacket that solidifies your status as queen of the night.
25. Sole Society Flynn Bootie ($110): Step out of your #sandalsornothing routine and sashay into fall with versatile suede booties that can be worn on the daily. From a lazy girl-approved sweater dress to a down-to-business jumpsuit, these of-the-moment stompers won’t let you down.
Brit + Co may at times use affiliate links to promote products sold by others, but always offers genuine editorial recommendations.
