Dresses with Boots Outfit Ideas to Wear for Winter 2024
If your cold weather ensembles feel weighed down by the monotony of bulky sweaters and trousers, it’s time to venture out into a chic outfit combo we’re loving right now: Boots and Dresses.
This feminine silhouette is a polished look for work, date night and everyday. We’re giving you the rundown on three trending boot silhouettes, which dresses to wear with tall boots and how to layer these pieces to stay warm.
Want more styling ideas? Check out more articles by Los Angeles Personal Stylist Meg Gallagher, or set up a style consultation with Meg here:
Things to Consider Before Shopping for Tall Boots:
There are a couple things to consider before shopping for tall boots:
1. Measure BOTH Calves! (If one calf is bigger than the other, defer to the larger calf for boot sizing.) Understanding which boots are right for you can be whittled down by first comparing the measurement of your calves with the shaft of the boot. If you have athletic calves, consider extended sizing. Inclusive brands like Vince Camuto offer Women’s Wide & Extra Wide Calf Boots for those who need the extra room.
2. Consider the height of your legs. If you have shorter or taller legs, you may need petite or tall sized boots. Consider brands like Duo Boots who offer specialty sizing petite and extra tall boots.
3. Consider your desired heel height and heel preferences.
High heeled boot silhouettes are available for those who enjoy the added height. Block heels are great for added walkability.
Low heeled boots are a great alternative shoe that still offer an elevated look without needing the height of a heel.
Comfort is Key: Riding Boots with Sweater Dresses
Riding boots are trending for 2024-2025 for their sleek minimalism, knee-high silhouette and walkability. If you need an easy boot to carry you through winter, you’ll love this boot’s ultra-walkable low heel. This casual boot looks amazing with equally casual sweater dresses. Utilize sheer patterned tights to fill in the space between your boot and leg for warmth and added texture into your outfit.
Combination to Try:
Pair a mini or midi sweater dress with tights, riding boots, a jacket or blazer and a matching bag/belt/accessories.
Shop our edit of riding boots and casual fall dresses here:
Timeless Work Look: Midi Dresses and Heeled Boots
Heeled tall boots look great with a midi dress layered over the top for work or going out. Dig up your winter florals, button up dresses, leather, silk and pattern wrap dresses to pair with your boots. Finish off the look with a blazer or coat.
We love this look with midi knit dresses for winter.
Shop our edit of heeled boots and winter midi dresses here:
Hot & On-Trend: Moto Boots, Leather Jacket and a Dress
If you want an on-trend look that serves sweetness with some edge, pair your moto boots and leather jacket with a dress underneath. Bonus points if you add some floral tights, bows or lace to keep the style high-contrast. This look is great for going out and date night!
The Key to This Look:
Balance edgy moto boots and a leather jacket with a dress and tights or knee socks.
Styling tip: Socks and Legwarmers
Let some knee socks or leg warmers show at the top of your moto boots.
Styling tip: Sheer Tights
Punky moto boots look great with sheer tights.
Shop our edit of moto boots, leather jackers and winter mini dresses here:
