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Outfits to Wear With Boots 2019

10 Affordable Outfits to Wear With Boots Now and Through Fall

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There are a lot of things we love about Fall fashion, but boots rank pretty dang high on our lists. Think about it: What other accessory truly defines the season more than boots? Nothing! OK, that might be a bit dramatic, there are plenty of other cool-weather accessories we love from loafers to textured bags and hats. But boots just get us especially excited for Fall, which is why we're already planning fresh outfit formulas to wear with all our favourite styles.

Now, I know what you're thinking: Summer isn't over, nor do you want it to end. I'm with you! I live for a breezy dress-and-sandal look on a balmy Summer day. However, right now is when all of our favourite stores and brands are debuting their new Fall arrivals, so there's no better time to start preparing a fresh lineup of outfits for the new season. And as you might guess, we're all for said looks to centre around your favourite boots.

Whether you tend toward classic styles, Western silhouettes, or are all about trendy animal print, ahead, get inspired by the 10 super-stylish outfits that centre around boots, courtesy of fashion influencers we love. And because we want you to be as prepared as possible for the new season, we shopped out each outfit head-to-toe, all with affordable pieces including under-$100 styles from our very own POPSUGAR collection at Kohl's.

Image Source: Instagram / @alyssainthecity

Bright colours are staking their claim for Fall from super-saturated shades to sweet pastels. As a fun and unexpected pairing, try styling western boots with a colourful top and floaty skirt which will easily skim over the top of the boots.

POPSUGAR Short Sleeve Sweatshirt ($27, originally $36)

Image Source: kohls.com
POPSUGAR Short Sleeve Sweatshirt
$27
from kohls.com
Buy Now

POPSUGAR Midi Skirt ($37, originally $50)

Image Source: kohls.com
POPSUGAR Midi Skirt
$37
from kohls.com
Buy Now

Charles Albert Western Style Embroidered Cowboy Boots ($35)

Image Source: amazon.com
Charles Albert Western Style Embroidered Cowboy Boots
$35
from amazon.com
Buy Now

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Charles & Keith Textured Saddle Bag ($59)

Image Source: charleskeith.com
Charles & Keith Textured Saddle Bag
$59
from charleskeith.com
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Animal prints are going bolder for Fall, both in brighter colours and less-common motifs like cow, zebra, and tiger. To temper the effect of an printed jacket-and-skirt set, layer a fitted mock-neck top in a softer colour underneath and finish off the look with versatile black boots. Bonus points for a tough, lug-sole pair.

POPSUGAR Elbow Sleeve Mockneck Top ($27, originally $36)

Image Source: kohls.com
POPSUGAR Elbow Sleeve Mockneck Top
$27
from kohls.com
Buy Now

Collusion Snake Print Trucker Jacket & Mini Skirt Two-Piece Set ($58, originally $96)

Image Source: us.asos.com
Collusion Snake Print Trucker Jacket & Mini Skirt Two-Piece Set
$58
from us.asos.com
Buy Now

Steve Madden Gretta Boots ($140)

Image Source: stevemadden.com
Steve Madden Gretta Boots
$140
from stevemadden.com
Buy Now

Express Chain Strap Wallet ($30)

Image Source: express.com
Express Chain Strap Wallet
$30
from express.com
Buy Now

Feminine dresses are staples year-round, but to extend the life of your favourite Summer version, simply swap your sandals for boots a toss a trench over top when you need a warmer layer.

& Other Stories Belted Trench Coat ($149)

Image Source: stories.com
& Other Stories Belted Trench Coat
$149
from stories.com
Buy Now

POPSUGAR Ruffle Trim Swing Dress ($37, originally $50)

Image Source: kohls.com
POPSUGAR Ruffle Trim Swing Dress
$37
from kohls.com
Buy Now

Dr. Martens Leona Heeled Boot ($160)

Image Source: shop.nordstrom.com
Dr. Martens Leona Heeled Boot
$160
from shop.nordstrom.com
Buy Now
Advertiser content from Kohl's

LC Lauren Conrad Lydia Round Crossbody Mini Bag ($34, originally $49)

Image Source: kohls.com
LC Lauren Conrad Lydia Round Crossbody Mini Bag
$34
from kohls.com
Buy Now

Fall dress silhouettes run the gamut, but longer hemlines are a fresh-from-the-runway look to try, especially in a powdery soft hue. To give yours a cool-weather spin, team yours with sleek boots and add a cosy teddy coat into the mix when the cold really hits.

POPSUGAR Teddy Coat ($73, originally $98)

Image Source: kohls.com
POPSUGAR Teddy Coat
$73
from kohls.com
Buy Now

Universal Standard Katherine Side Tie Knot Dress ($120)

Image Source: universalstandard.com
Universal Standard Katherine Side Tie Knot Dress
$120
from universalstandard.com
Buy Now

Mango Snake-Effect Ankle Boots ($100)

Image Source: shop.mango.com
Mango Snake-Effect Ankle Boots
$100
from shop.mango.com
Buy Now

Massimo Dutti Snakeskin-Effect Leather Bag ($199)

Image Source: massimodutti.com
Massimo Dutti Snakeskin-Effect Leather Bag
$199
from massimodutti.com
Buy Now

The easiest way to make your tee-and-jeans outfits into Fall? With a pair of boots! To liven up the look even more, go for a printed jacket and finish with a polished bag.

Everlane The Square Mockneck Tee ($25)

Image Source: everlane.com
Everlane The Square Mockneck Tee
$25
from everlane.com
Buy Now

Urban Outfitter Markey Patchwork Quilted Shirt Jacket ($99)

Image Source: urbanoutfitters.com
Urban Outfitter Markey Patchwork Quilted Shirt Jacket
$99
from urbanoutfitters.com
Buy Now

POPSUGAR Embroidered Midrise Straight-Leg Jeans ($37, originally $50)

Image Source: kohls.com
POPSUGAR Embroidered Midrise Straight-Leg Jeans
$37
from kohls.com
Buy Now

Topshop Maja Leather Black Sock Boots ($160)

Image Source: us.topshop.com
Topshop Maja Leather Black Sock Boots
$160
from us.topshop.com
Buy Now

COS Small Leather Crossbody Bag ($89)

Image Source: cosstores.com
COS Small Leather Crossbody Bag
$89
from cosstores.com
Buy Now

Fall is all about texture and a fun way to experiment is by blending fabrics and prints. For a fashion-girl with a relaxed feel, style a simple sweatshirt underneath a leather jacket and printed pants. For the finale, a pair of snake-print boots feels totally fresh.

Bershka Faux Leather Overshirt Jacket ($70)

Image Source: bershka.com
Bershka Faux Leather Overshirt Jacket
$70
from bershka.com
Buy Now

POPSUGAR Snap-Side Sweatshirt ($18, originally $44)

Image Source: kohls.com
POPSUGAR Snap-Side Sweatshirt
$18
from kohls.com
Buy Now

Zara Floral Printed Flared Pants ($50)

Image Source: zara.com
Zara Floral Printed Flared Pants
$50
from zara.com
Buy Now

Dolce Vita Bel Booties ($140)

Image Source: dolcevita.com
Dolce Vita Bel Booties
$140
from dolcevita.com
Buy Now

My Accessories London Black Mock Croc 90s Shoulder Bag ($35)

Image Source: us.asos.com
My Accessories London Black Mock Croc 90s Shoulder Bag
$35
from us.asos.com
Buy Now

We get it, you don't want to retire your Summer dresses just yet. And there's no need! For in-between weather, punctuate your favourite maxis with a lighter pair of boots, and voilà! You're done. Later in the season, simply top the look with a textured blazer or coat.

POPSUGAR Belted Maxi Dress ($48, originally $64)

Image Source: kohls.com
POPSUGAR Belted Maxi Dress
$48
from kohls.com
Buy Now

Nasty Gal Run Off Your Feet Croc Faux Leather Boots ($40, originally $80)

Image Source: nastygal.com
Nasty Gal Run Off Your Feet Croc Faux Leather Boots
$40
from nastygal.com
Buy Now

A button-down shirt and jeans are another fail-safe way to style your boots during transitional weather. To give this classic combo a playful feel, opt for a piece in animal print, whether it's your top, bag, or boots.

POPSUGAR Essential Button Down Shirt ($33, originally $44)

Image Source: kohls.com
POPSUGAR Essential Button Down Shirt
$33
from kohls.com
Buy Now

Levi's Ribcage Wide Leg Jeans ($98)

Image Source: levi.com
Levi's Ribcage Wide Leg Jeans
$98
from levi.com
Buy Now

ALDO Drerissa Boots ($75, originally $150)

Image Source: pullandbear.com
ALDO Drerissa Boots
$75
from aldoshoes.com
Buy Now

ASOS DESIGN Micro 90s Bag ($24)

Image Source: us.asos.com
ASOS DESIGN Micro 90s Bag
$24
from us.asos.com
Buy Now

Another dress-and-boot combo to try now, during transitional weather, and into early Fall is a feminine silhouette with light suede boots. Whether your dress of choice features puffy sleeves, a ruffled hemline, or so-sweet print, a beige-coloured boot with clean lines is sure to pair perfectly.

POPSUGAR Button-Up Midi Dress ($48, originally $64)

Image Source: kohls.com
POPSUGAR Button-Up Midi Dress
$48
from kohls.com
Buy Now

When styling boots for the office, think outside the box and try your hand at a casually tailored look via a fitted mock-neck top, belted blazer, and jogger-style trousers. The result: polished with impact.

Pixie Market Briana Belted Black Blazer ($179)

Image Source: pixiemarket.com
Pixie Market Briana Belted Black Blazer
$179
from pixiemarket.com
Buy Now

Babaton Wade Jogger Pant ($148)

Image Source: aritzia.com
Babaton Wade Jogger Pant
$148
from aritzia.com
Buy Now

POPSUGAR Elbow Sleeve Mockneck Top ($27, originally $36)

Image Source: kohls.com
POPSUGAR Elbow Sleeve Mockneck Top
$27
from kohls.com
Buy Now

Forever 21 Faux Leather Booties ($40)

Image Source: forever21.com
Forever 21 Faux Leather Booties
$40
from forever21.com
Buy Now

Glamorous Two Tone Structured Shoulder Bag ($45)

Image Source: us.asos.com
Glamorous Two Tone Structured Shoulder Bag
$45
from us.asos.com
Buy Now

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