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31 Fall Outfit Ideas For October, Now That Cool Weather Is Finally Approaching

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By now, you have a few chilly, cloudy days under your belt. Fall is finally here, and with it comes what may be the most fun styling opportunities you've had so far in 2019. Here's the thing about getting dressed this time of year: it's all about smart layering. Your best fall outfit ideas for October utilize some of your favorite pieces from summer — like floaty slip dresses, and bold accessories — but add cozier pieces into the mix too.

For anyone who enjoys the art of putting together a full-on outfit, this is the time to shine. It's not so hot that a cotton maxi is all you can manage, and not so cold that your outfit is centered around maintaining body heat when you step outside. You literally have the run of your entire closet, not to mention the major looks of the season. So, make the most of October, and have fun getting dressed. Embrace the season's biggest trends, including bold colors like Pistachio green, statement accessories including Staud's Moon Bag, and suiting mixed and matched with abandon. Below, you'll find an outfit idea for every single day of October, to help you embrace the chilly temps and put your best foot forward from now until Halloween.

Soft & Tough

An oversized blazer and cool boots balance a swingy skirt.

Cool Coordination

Go for a statement look by styling a printed dress with a coat in the same bright hue.

Texture Play

Try out different textures by layering leather and pleats and finishing with a statement bag.

Trench Coat Classic

A trench coat lends a cool fall feel to the looks you've worn all summer.

Topped With Leather

A leather top is a cool alternative to your typical jacket.

Bold Boots

Sleek white boots are a classic fall staple for a sunny day.

The Reimagined Button-Down

Break out your fall button-down in a whole new way by only buttoning the top half.

Sleek Styling

Try mixing textures but wear a single color head to toe.

All About The Shoe

Balance out a bold outfit with a pair of cool brogues or creepers.

Totally Tonal

Embrace an all-neutral look by opting for slightly off-tones all together at once.

Great Basics

If you want to keep things simple, opt for an ensemble of well-tailored basics. Finish off with a statement bag.

Endless Summer

Bring your favorite summery top into fall by throwing a long coat over the top.

Underwear Out

Though it may not fly at the workplace, try giving suiting a more casual appeal by styling with your favorite bra or lingerie top.

Come Any Weather

For those transitional days, keep a sweater on hand by tying it around your shoulders instead of a scarf.

Dark Denim

If light-wash denim feels too summery to you, try swapping for pieces in a deep navy or faded black. Then, opt for a tan bag to balance the look.

Chic Sweater

Now that sweater weather has arrived, try styling yours with high-waisted pants and a pair of sneakers.

All About Trousers

You don't have to wear a full suit to embrace a great pair of trousers. Style yours with a tee or button-down top for a non-fussy look.

Dressed-Up Outerwear

To help you with the seasonal transition, consider pieces that toe the line between two looks, like a coat dress that you can easily dress up with boots or heels.

Color Story

Don't be afraid to embrace bold color this fall. Opt for a tonal ensemble and finish with statement accessories to round out the look.

Smart Staples

Can't decide between a knit or a blazer? Find a piece that is a bit of both.

Cool And Comfortable

Yes, you can dress up a cozy coat. Add cool snakeskin boots and jeans to give a sporty topper a dressed up feel.

Cozied Up

While leggings may not be your first instinct for a weekday look, try styling them with a sweater and boots for a more polished take.

Smart Styling

If you're somewhere where temperatures tend to fluctuate throughout the day, shorts and a sweater are an ideal combination for navigating the changes.

Pumpkin Spice

Fall is the season for pumpkin spice, so find a place for it in your wardrobe. Rich yellow-orange is a warm tone that looks great on everyone.

All About Texture

Try mixing up your textures this season and layer rich shearling or tweed with leather and patent leather. The combo feels just right for cooler days.

Cool Capes

A wrap scarf or cape is a smart alternative to your usual coats. But, if you're not sure how to style it, perhaps try a blouse or jacket with the draping built in.

Dress Up, Dress Down

Don't be afraid to dress up your more casual, cozy pieces like a sweatshirt or long sleeve tee. Pair with a sleek slip skirt and boots, and you're ready to head out the door.

Epic Accessories

Don't underestimate the power of a great accessory like an unexpected statement hat or a geometric, structured bag.

Pajama Chic

On those days when you're not so motivated to leave the house, try layering oversized separates for a polished twist on just-rolled-out-of-bed dressing.

Blazer & Boots

A tough pair of combat boots are the perfect balance to dressier pieces like a floaty slip and blazer.