31 Outfit Ideas to Make October Dressing a Breeze

While many consider September the official beginning of fall, temperatures don’t actually warrant autumn dressing until the time for October outfits hits (so, you know, today). In fact, some might argue that this is the best month for dressing because it’s cool enough to break out the knitwear and boots, but still warm enough to keep your puffer coats and scarves tucked away for the time being. Some days might be crisp enough for tights; others, a well-placed pair of socks will do. Really, it’s the perfect time to really play with fashion — enter, layering — because there isn’t much by way of extreme weather to worry about.

That said, despite this sense of seasonal change and endless style potential, it might take some practice to get back in the swing of sweaters and jeans and such after months of sweltering heat. To aid in this shift, TZR has scoured for 31 perfect looks that you can copy — right now. There’s a mix of vibes, ranging from androgynous suiting to festive evening attire (hint: feathers). Whatever your personal style might be, there’s likely a look (or 31) you’ll be able to take inspiration from ahead. And if you’ve discovered a gap or two in your wardrobe, there’s a shopping pick accompanied with each combination to help you feel all the more prepared for the weeks ahead.

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A Go-To Handbag

A closet companion! A chic keeper of things! An outfit completer! The go-to handbag is a fall staple and if you’ve yet to find yours, a saddle bag silhouette in classic black is a great place to start.

Plaid Mini Skirt

There are few (if any) patterns more synonymous with autumn than a cozy plaid. Grab a mini skirt in the seasonal print and pair it with socks and heels for a nod to collegiate style.

After-Hours LBD

Fall kicks off the season of festive holiday parties, and you’ll be needing something to wear to all of them. A little black dress that’s crafted in an alluring material (think: mesh or lace) will always feel right.

Slouchy Jeans

Did you hear? Baggy jeans are the denim silhouette du jour these days. Style your relaxed pair with seasonal favorites like chunky cardigans and crisp button downs.

Back-to-Work Suit

Not just for boardrooms, the pantsuit has reinvented itself over the years into a staple set for personal styles across the board. Try one in brown to kick off the cooler months of the year.

The Moody Necklace

Imbue your personal style with a touch of goth via a black cord necklace. The look feels plucked from a ‘90s Halloween film (Practical Magic and The Craft, to name a couple).

Leather Blazer

Instead of the traditional wool blazer, swap yours out for one crafted in leather (vegan or real). It adds the perfect depth in texture and goes with just about anything.

The Neutral Waistcoat

If you live somewhere that has moderate temperatures (as in, no coat needed) you can still make your wardrobe feel autumnal with tailored separates, like a waistcoat. Wear with matching slacks to work or loose denim for the weekend.

Pajama Pants

Treat your silk pajama pants to an outing and combine them with a long trench coat and chunky sneakers — the result will be effortless and cool, from head-to-toe.

Ruffled Blouse

If the beginning of fall has you longing for Pride and Prejudice-style whimsy, slip into a ruffled Victorian-inspired blouse and modernize it with layered necklaces and a leather blazer.

A House Dress

Regardless if you’re working from the couch or in the office, a charming house dress is always a reliable piece to have on hand. Jazz up the look by layering a printed bralette on top.

Staple Midi Skirt

If you hate puzzling over what to wear in the morning, invest in a classic midi skirt that you can mix and match with anything. A great combination to begin with? A belted blazer and block heels.

Sleek Clogs

For days when comfort is the priority, a long-sleeve maxi dress worn with clogs is a stylish pairing. If you appreciate the ‘90s aesthetic, add in a choker.

Cheery Raincoat

The easiest way to defray the gloominess of a rainy day is a cheery raincoat, naturally. Go for one in a bright color or playful print.

Vibrant Dress

Don’t avoid bright colors once the weather turns colder — a bold dress is easy to slip into and instantly perks up your mood.

Moto Jacket

The moto jacket is a perennial favorite thanks to its casual-cool aesthetic and versatility (it can go with a silk slip dress and a tee and jeans).

Silk Scarf

While a silk headscarf feels reminiscent of carefree summer days, it also translates to fall and winter quite well, too. Wear yours with a pantsuit to soften the tailored look.

Heeled Loafers

Pep up your step with a pair of heeled loafers. They have the same sensibilities as their flat counterparts, but can make an outfit feel slightly dressier.

Fancy Outerwear

While you may have to wait until the end of October to wear it, now is a good time to secure your coat for late fall and winter. If you love texture, consider a feather or faux fur-trimmed coat in a unique colorway.

Double the Denim

Have nothing to wear? Not if you have a denim jacket and jeans in your closet. Pair these two together with a striped tee or colorful knit for a quick and easy look that always feels stylish.

Sweater Vest

An MVP among fall layering pieces, the sweater vest is perfect for the month of October when temperatures aren’t cold enough to warrant a cashmere turtleneck, but chilly enough to justify a cozy knit.

Cargo Pants

This has been a good year for cargo pants thus far, so keep the trend alive by wearing yours with soft sweaters all season long. Dress up the look with boots or keep things low-key with sneakers.

Artful Cutouts

One of the best details to come out of the ‘sexy dressing’ trend is the cutout. While a pair of pants with a thong-shaped cutout might feel too bold at times, a dress with unique slashes is a lovely way to carry the look into fall festivities.

A Cute Cap

If you find yourself googling Carolyn Bessette-Kennedy outfit images every time fall comes around, it’s a good idea to invest in effortless, unfussy staples. Start with a baseball cap.

Cold-Weather Pleats

Channel boarding school days of yore with a pleated wool skirt crafted in a seasonal shade of gray or brown. For extra credit, wear it over a pair of pants.

Commuter Sneakers

If you live in a commuter city, you’re likely hopping on public transportation more frequently these days to get to work. Heels and subways don’t mix, so grab a pair of stylish trainers to make your transit more comfortable.

Colorful Knit

There’s power in wearing a vibrant color during the colder months of the year, and purple in all different hues is a universally flattering choice. If it’s still a bit toasty out, you can knot yours around your shoulders for now.

Crisp Button-Down

Outfit assembling is made easier with wardrobes tables like a crisp white button-down shirt. You can style it with everything from trousers and skirts to jeans — or even layer it under a slip dress (cropped tops are best for this).

Drapey Trench Coat

The time for puffer jackets and chunky wool coats will come, but for now, enjoy the autumn months when all you need is a drapey trench coat. If it’s warm enough, wear yours with a sweater and mini skirt.

Something Festive

They don’t call it the return of The Roaring Twenties for nothin’ — embrace the celebratory mood of late and grab a feather-embellished piece for the holiday parties to come. Or, simply wear yours to a weekend dinner, any excuse will do.

Dress Over Pants

Prolong the life of your favorite dresses by styling them over a pair of simple, neutral-colored trousers. This look is especially great when done in all-black and with a pair of chic mules (as proven above).