Best Dresses to Wear With Boots
If You're Unsure About Wearing Dresses With Boots, I'm Here to Convince You
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With cold snaps now on the forecast, I have been thinking of cosy outfit combinations that don't only involve jeans or trousers. Looks that don't require setting aside my dresses but instead transitioning them into a new season, thus allowing me to get more wear out of all the clothes in my closet. Luckily, with the addition of the right coat, some tights, and boots, even the flimsiest dress can be turned into a chic winter look that packs ample warmth and style.
My guiding style principle when it comes to wearing dresses with boots is to mind the proportions. Ideally, any combination of the two would serve to either elongate, support, or enhance your figure, rather than appear forced or constricted. Scroll on to see some styling examples and to shop some seriously stylish dresses that will work for frigid temperatures or sunnier days.
Pair a Midi Dress With Tall Riding Boots
A halter-style checkered dress paired with an equally eye-catching cardigan and tall black boots makes a chic winter-ready look.
Keep It Polished With Tall Heeled Boots and a Tailored Leather Coat
A thicker midi knit dress can protect you from the cold when paired with knee-high heeled boots and a sharp trench coat.
Add Warmth With a Sweater-Turned-Scarf, and Some Chelsea Boots
Chelsea boots make a practical finish to almost every look, including a maxi-style puff sleeve printed dress.
Achieve Cosy Status With a Puffer Coat and Tall Snakeskin Boots
A Sunday Dress: Nasty Gal Ribbed Wrap Panel Midi Dress
This Nasty Gal Ribbed Wrap Panel Midi Dress ($18, originally $60) feels like a Sunday dress with its easy elegance and comfort, don't you agree? It's made in a stretchy ribbed jersey that will make it a joy to wear. At home, pair it with slippers or bring out your favourite kitten heels or boots if you have to step out.
A Funky Print: Nasty Gal Abstract Check Mesh Funnel Neck Midi Dress
This pop-inspired Nasty Gal Abstract Check Mesh Funnel Neck Midi Dress ($24, originally $79) is effortlessly cool, plus the silhouette is easygoing, so you'll be wearing it on repeat. Make it edgy with chunky boots and a leather jacket.
A Special Occasion: OPT Gertie Dress
Reserve this OPT Gertie Dress ($82, originally $137) for dressy occasions like a hot date or office party. The asymmetrical cutout is unexpectedly playful, definitely dialing up the allure. Pair it with tall heeled boots or strappy heels.
A Day-to-Night Ensemble: Line & Dot Sylvie Sweater Dress
This Line & Dot Sylvie Sweater Dress ($77, originally $110) features thigh-high side slits and a one-shoulder neckline with a ribbed panel for a sleek, asymmetrical ensemble. It works both for daytime and nighttime outings.
A Day-to-Night Look: ASTR the Label Twist Front Long Sleeve Sweater Dress
This ASTR the Label Twist Front Long Sleeve Sweater Dress ($89) will charm everyone at the next brunch party or office gathering. We love the neckline and fitted rib fabric.
A Side-Slit Entry: ASTR the Label Long Sleeve Side Slit Sweater Dress
This ASTR the Label Long Sleeve Side Slit Sweater Dress ($79) features a side slit that dials up the allure (and sass). We love the cold-weather-friendly ribbed fabric and mock-neck silhouette.
A Sleek First Impression: AFRM Shailene Long Sleeve Mesh Dress
The gauzy mesh fabric of this AFRM Shailene Long Sleeve Mesh Dress ($88) dials up the sex appeal. Save it for a chic dinner or an exciting first date.
Royal Purple: H&M High-Sheen Dress
This H&M High-Sheen Dress ($25) has a certain regal elegance, thanks to the choice of purple, shimmering fabric, and easygoing fit.
Some Cutout-Shoulder Action: Enza Costa Silk Rib Angled Neck Midi Dress
This Enza Costa Silk Rib Angled Neck Midi Dress ($225) oozes sex appeal, confidence, and femininity. It's a great one to dress up or down, depending on the occasion.
For Date Night: Wayf Split V Ribbed Midi Dress
This sleek Wayf Split V Ribbed Midi Dress ($62, originally $138) features a flattering cutout neckline that makes it irresistibly chic. Finish the look with a wool coat and low heeled sandals.
A Relaxed Silhouette: Line & Dot Camilla Knit Ribbed Shirt Dress
This Line & Dot Camilla Knit Ribbed Shirt Dress ($69, originally $99) is an earthy spin on your traditional shirt dress, and we love the rich yet understated colour. Complete your outfit with sneakers or loafers for casual runs.
An Office-Ready Dress: Good American Long Sleeve Polo Midi Dress
If you want a professional-looking dress that is also stylish, we found your match. The Good American Long Sleeve Polo Midi Dress ($104, originally $149) is easy to dress up with heels and down with sneakers. Plus, the rib-stitched material makes it comfortable enough to wear all day.
An Open-Back Statement: Nasty Gal Knitted Ribbed Midi Dress
Show off your back in an elegant way in this Nasty Gal Knitted Ribbed Midi Dress ($18, originally $59), which features a high neck, a relaxed silhouette, and long sleeves. Style it with strappy heels for date night.
A Cool Print: Printed Short Dress
We love a printed dress, so this Printed Short Dress ($50) immediately caught our attention. It has a relaxed yet put-together air that makes it a winner in our books.
A Classic Silhouette: Gold Button Knit Dress
This Gold Button Knit Dress ($50) has a timeless quality that'll make it one you turn to season after season. Pair it with tall heeled boots for a polished and preppy look.
Effortless Elegance: H&M+ Lace-Trimmed Slip Dress
This H&M+ Lace-Trimmed Slip Dress ($35) oozes easy elegance, plus the fabric has a luxe appeal. Style it with a blazer for the office, and on its own with mules for date night.
A Wardrobe Staple: Rib-Knit Dress
This Rib-knit Dress ($50) is not only winter-friendly, but the fit is comfortable and flattering. You'll have no problem going about your days in ease.
A Polished Dress With Dolman Sleeves
Meeting the parents or headed for an interview? This Dress With Dolman Sleeves ($25) will convey confidence, femininity, and easy elegance.
Old Navy Tie-Neck 3/4-Sleeve Maxi Swing Dress
Some breezy dresses look too summery but this Old Navy Tie-Neck 3/4-Sleeve Maxi Swing Dress ($50) is one we'd reach for year-round (in either solid black or a dark black floral pattern).
For a Cool Print: AllSaints Melody Pembury Midi Slipdress
The print and silhouette of this AllSaints Melody Pembury Midi Slipdress ($117, originally $259) make it stylish and airy. Pair with sneakers for a laid-back look or low-heeled mules for a dressier appearance.
