Popsugar Fashion Outfits Outfits to Wear With Boots 2019 10 Affordable Outfits to Wear With Boots Now and Through Fall 23 August 2019 by Laura Lajiness Kaupke Image Source: Instagram / @alyssainthecity As POPSUGAR editors, we independently select and write about stuff we love and think you'll like too. If you buy a product we have recommended, we may receive affiliate commission, which in turn supports our work. 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. 1 Wear Your Boots With: A Colourful Top and Skirt View this post on Instagram can't take the south outta the girl. in the Billie boot by @thefryecompany ❤ #inmyFRYE A post shared by alyssa coscarelli (@alyssainthecity) on Nov 5, 2018 at 5:47am PST 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. 2 Shop the Look Image Source: kohls.com POPSUGAR Short Sleeve Sweatshirt ($27, originally $36) POPSUGAR Short Sleeve Sweatshirt $27 from kohls.com Buy Now 3 Shop the Look Image Source: kohls.com POPSUGAR Midi Skirt ($37, originally $50) POPSUGAR Midi Skirt $37 from kohls.com Buy Now 4 Shop the Look Image Source: amazon.com Charles Albert Western Style Embroidered Cowboy Boots ($35) Charles Albert Western Style Embroidered Cowboy Boots $35 from amazon.com Buy Now 5 Shop the Look Image Source: charleskeith.com Charles & Keith Textured Saddle Bag ($59) Charles & Keith Textured Saddle Bag $59 from charleskeith.com Buy Now 6 Wear Your Boots With: An Animal Print Set View this post on Instagram Mood 🖤 A post shared by Brittany Xavier (@brittanyxavier) on Nov 20, 2018 at 9:01am PST 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. 7 Shop the Look Image Source: kohls.com POPSUGAR Elbow Sleeve Mockneck Top ($27, originally $36) POPSUGAR Elbow Sleeve Mockneck Top $27 from kohls.com Buy Now 8 Shop the Look Image Source: us.asos.com Collusion Snake Print Trucker Jacket & Mini Skirt Two-Piece Set ($58, originally $96) Collusion Snake Print Trucker Jacket & Mini Skirt Two-Piece Set $58 from us.asos.com Buy Now 9 Shop the Look Image Source: stevemadden.com Steve Madden Gretta Boots ($140) Steve Madden Gretta Boots $140 from stevemadden.com Buy Now 10 Shop the Look Image Source: express.com Express Chain Strap Wallet ($30) Express Chain Strap Wallet $30 from express.com Buy Now 11 Wear Your Boots With: A Dress and Trench Coat View this post on Instagram So ridiculously happy because my friends got me AirPods and it was warm enough to wear a dress @pamplemousseny (but threw on @drmartensofficial boots bc I can’t stand looking too much like a girl) 👨🏻✈️ A post shared by Kristen Lam (@kristengracelam) on Apr 27, 2018 at 7:05am PDT 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. 12 Shop the Look Image Source: stories.com & Other Stories Belted Trench Coat ($149) & Other Stories Belted Trench Coat $149 from stories.com Buy Now 13 Shop the Look Image Source: kohls.com POPSUGAR Ruffle Trim Swing Dress ($37, originally $50) POPSUGAR Ruffle Trim Swing Dress $37 from kohls.com Buy Now 14 Shop the Look Image Source: shop.nordstrom.com Dr. Martens Leona Heeled Boot ($160) Dr. Martens Leona Heeled Boot $160 from shop.nordstrom.com Buy Now Advertiser content from Kohl's 15 Shop the Look Image Source: kohls.com LC Lauren Conrad Lydia Round Crossbody Mini Bag ($34, originally $49) LC Lauren Conrad Lydia Round Crossbody Mini Bag $34 from kohls.com Buy Now 16 Wear Your Boots With: A Dress and Teddy Coat View this post on Instagram thank you @manouska_jay & @glossier fam for having me come talk tonight, it means the world to me 💚 A post shared by Lindsay Peoples Wagner (@lpeopleswagner) on Feb 13, 2019 at 6:18pm PST 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. 17 Shop the Look Image Source: kohls.com POPSUGAR Teddy Coat ($73, originally $98) POPSUGAR Teddy Coat $73 from kohls.com Buy Now 18 Shop the Look Image Source: universalstandard.com Universal Standard Katherine Side Tie Knot Dress ($120) Universal Standard Katherine Side Tie Knot Dress $120 from universalstandard.com Buy Now 19 Shop the Look Image Source: shop.mango.com Mango Snake-Effect Ankle Boots ($100) Mango Snake-Effect Ankle Boots $100 from shop.mango.com Buy Now 20 Shop the Look Image Source: massimodutti.com Massimo Dutti Snakeskin-Effect Leather Bag ($199) Massimo Dutti Snakeskin-Effect Leather Bag $199 from massimodutti.com Buy Now 21 Wear Your Boots With: A Top, Jacket, and Jeans View this post on Instagram #sponsored 〰️〰️ The @prada jacket of my #nyfw dreams thanks to @modaoperandi 💙 don’t forget to reserve the latest looks from fashion week online at @modaoperandi #mymoda #modaoperandi A post shared by * (@madelynnfurlong) on Feb 15, 2019 at 8:34am PST 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. 22 Shop the Look Image Source: everlane.com Everlane The Square Mockneck Tee ($25) Everlane The Square Mockneck Tee $25 from everlane.com Buy Now 23 Shop the Look Image Source: urbanoutfitters.com Urban Outfitter Markey Patchwork Quilted Shirt Jacket ($99) Urban Outfitter Markey Patchwork Quilted Shirt Jacket $99 from urbanoutfitters.com Buy Now 24 Shop the Look Image Source: kohls.com POPSUGAR Embroidered Midrise Straight-Leg Jeans ($37, originally $50) POPSUGAR Embroidered Midrise Straight-Leg Jeans $37 from kohls.com Buy Now 25 Shop the Look Image Source: us.topshop.com Topshop Maja Leather Black Sock Boots ($160) Topshop Maja Leather Black Sock Boots $160 from us.topshop.com Buy Now 26 Shop the Look Image Source: cosstores.com COS Small Leather Crossbody Bag ($89) COS Small Leather Crossbody Bag $89 from cosstores.com Buy Now 27 Wear Your Boots With: A Sweatshirt, Jacket, and Pants View this post on Instagram Man I missed my city. NY, NY. Snake print heels c/o @dolcevita 🖤 #ad A post shared by ANAA SABER (@oursecondskin) on Feb 6, 2019 at 5:44pm PST 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. 28 Shop the Look Image Source: bershka.com Bershka Faux Leather Overshirt Jacket ($70) Bershka Faux Leather Overshirt Jacket $70 from bershka.com Buy Now 29 Shop the Look Image Source: kohls.com POPSUGAR Snap-Side Sweatshirt ($18, originally $44) POPSUGAR Snap-Side Sweatshirt $18 from kohls.com Buy Now 30 Shop the Look Image Source: zara.com Zara Floral Printed Flared Pants ($50) Zara Floral Printed Flared Pants $50 from zara.com Buy Now 31 Shop the Look Image Source: dolcevita.com Dolce Vita Bel Booties ($140) Dolce Vita Bel Booties $140 from dolcevita.com Buy Now 32 Shop the Look Image Source: us.asos.com My Accessories London Black Mock Croc 90s Shoulder Bag ($35) My Accessories London Black Mock Croc 90s Shoulder Bag $35 from us.asos.com Buy Now 33 Wear Your Boots With: A Dress View this post on Instagram may have mastered riding a bike in the rain + getting my dress wrinkly enough for it to look intentional 🤷🏻♀️ A post shared by lauren caruso (@laurencaruso_) on Aug 18, 2019 at 7:25am PDT 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. 34 Shop the Look Image Source: kohls.com POPSUGAR Belted Maxi Dress ($48, originally $64) POPSUGAR Belted Maxi Dress $48 from kohls.com Buy Now 35 Shop the Look Image Source: nastygal.com Nasty Gal Run Off Your Feet Croc Faux Leather Boots ($40, originally $80) Nasty Gal Run Off Your Feet Croc Faux Leather Boots $40 from nastygal.com Buy Now 36 Wear Your Boots With: A Shirt and Jeans View this post on Instagram Throw it on A post shared by Reese Blutstein (@double3xposure) on Jan 4, 2019 at 2:25pm PST 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. 37 Shop the Look Image Source: kohls.com POPSUGAR Essential Button Down Shirt ($33, originally $44) POPSUGAR Essential Button Down Shirt $33 from kohls.com Buy Now 38 Shop the Look Image Source: levi.com Levi's Ribcage Wide Leg Jeans ($98) Levi's Ribcage Wide Leg Jeans $98 from levi.com Buy Now 39 Shop the Look Image Source: pullandbear.com ALDO Drerissa Boots ($75, originally $150) ALDO Drerissa Boots $75 from aldoshoes.com Buy Now 40 Shop the Look Image Source: us.asos.com ASOS DESIGN Micro 90s Bag ($24) ASOS DESIGN Micro 90s Bag $24 from us.asos.com Buy Now 41 Wear Your Boots With: A Dress View this post on Instagram Guys, I have to admit: I’m feeling very special after being at @tanyataylor’s fashion week lunch, which she’s now thrown for two years in lieu of a presentation. Our paths have crossed many times over the years I’ve been in New York. First, I was one of her interns thanks to a friend who worked on the brand. Later, I interviewed her from time to time while I was a fashion editor. And eventually, we worked on one of my favorite-ever projects from my time at @glamourmag: making runway garments for @aidybryant—soon after for her, extended size ready-to-wear. (Plus, fun fact, we are both 🇨🇦!) As a person and as a brand, she’s into helping others rise and today’s lunch was all about women who have started companies. The @negativeunderwear, @unboundbabes, and @celsious_social founders were there. As I keep at it with @henning I’m trying to remember to value motivational moments like this. Thank you @tanyataylor. 🙏🏼 PS. If you have any inspiring pep talks for me leave ‘em below! 💪🏼 (📸: @eiffeltyler) A post shared by LAUREN CHAN (@lcchan) on Feb 9, 2019 at 12:46pm PST 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. 42 Shop the Look Image Source: kohls.com POPSUGAR Button-Up Midi Dress ($48, originally $64) POPSUGAR Button-Up Midi Dress $48 from kohls.com Buy Now 43 Wear Your Boots With: A Top, Blazer, and Pants View this post on Instagram Side eyeing all the packing I have yet to do. T-a few hours until ✈️ JAPAN. Please drop recommendations!!! A post shared by JEANNE GREY (@thegreylayers) on Feb 28, 2019 at 3:37pm PST 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. 44 Shop the Look Image Source: pixiemarket.com Pixie Market Briana Belted Black Blazer ($179) Pixie Market Briana Belted Black Blazer $179 from pixiemarket.com Buy Now 45 Shop the Look Image Source: aritzia.com Babaton Wade Jogger Pant ($148) Babaton Wade Jogger Pant $148 from aritzia.com Buy Now 46 Shop the Look Image Source: kohls.com POPSUGAR Elbow Sleeve Mockneck Top ($27, originally $36) POPSUGAR Elbow Sleeve Mockneck Top $27 from kohls.com Buy Now 47 Shop the Look Image Source: forever21.com Forever 21 Faux Leather Booties ($40) Forever 21 Faux Leather Booties $40 from forever21.com Buy Now 48 Shop the Look Image Source: us.asos.com Glamorous Two Tone Structured Shoulder Bag ($45) Glamorous Two Tone Structured Shoulder Bag $45 from us.asos.com Buy Now ShoppingOutfitsOutfit IdeasStyle TipsFallFall ShoppingFall FashionBootsAccessoriesShoes