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Styling a dress with warm boots in the winter can be a challenge. For today’s Get Dressed With Merrick I’m walking you through wearing a dress with boots.

Wearing a Dress With Boots

Dresses can be hard to style during winter. Keeping your legs warm without looking too dressed-down is a hard balance, but I’m here to help.

For today’s Get Dressed With Merrick I’m going to walk you through a few looks and tips to wearing a dress with boots.

Try a sweater dress with a short jacket

A sweater dress is a great dress option during the winter. You could do a longer coat with it, but a shorter coat with a longer dress creates a more elongated shape.

You could do heeled boots, but also a flat Chelsea boot is great with a sock to soften the transition from boot to leg.

CHELSEA BOOTS | AMAZON SOCKS | LEATHER JACKET | SIMILAR SWEATER DRESS

Wear black tights with a dress and boots

If you’re heading somewhere nice and it’s super cold, wear black dressy boots and tights!

MW COLLECTION DRESS (wearing size small) | BLACK TIGHTS | BLACK BOOTS | PLAID COAT

Combat boots and a flowy dress are perfect together

If you want to try a taller boot, a lace up option like a combat boot is a great shoe!

A flowy dress creates great contrast to the slim and taller ankle boot. I added the belt for a flattering shape.

SIMILAR LEOPARD DRESS | AMAZON BELT | SIMILAR COMBAT BOOTS

Try a longer dress with a taller boot

If you need some extra warmth, a taller boot is a great option. These slouchy boots compliment a smooth dress like this (it’s actually a dress underneath the sweater)!

You can absolutely do a slouchy boot with a shorter dress too, but I’d recommend wearing one that hits above the top of your boot if you choose a shorter dress.

SIMILAR TEAL DRESS | SIMILAR CABLE KNIT SWEATER | SIMILAR KNEE HIGH BOOT | LEOPARD HEADBAND

Over the knee boots with a shorter dress

Over the knee boots are a great choice for longer or shorter dresses! I’m wearing a shorter dress here so there’s a gap in between the dress and the boots, but you could do a longer dress if you need more warmth.

SIMILAR FLORAL DRESS | AMAZON BELT | CIRCUS BY SAM EDELMAN OVER THE KNEE BOOTS

Try a fitted dress with ankle boots

A bodycon dress is great with ankle boots, both heeled and flat! You could also add a long or short coat with this kind of outfit.

SIMILAR GRAY BODYCON DRESS | SIMILAR TAN ANKLE BOOTS

I hope that’s helpful! No go wear your dresses and boots together — you’ve got this.

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How to Wear a Dress With Boots

Styling a dress with warm boots in the winter can be a challenge. For today’s Get Dressed With Merrick I’m walking you through wearing a dress with boots.

 

Wearing a Dress With Boots

A dress with boots can be hard to style during winter. Keeping your legs warm without looking too dressed-down is a hard balance, but I’m here to help.

For today’s Get Dressed With Merrick I’m going to walk you through a few looks and tips to wearing a dress with boots.

Merrick White Dress Denim Jacket Tan Chelsea Boots
chelsea-boots-dress

1. For a more casual look, try a Chelsea boot with your dresses

I love Chelsea boots so much, and they’re a great option for fall and winter with dresses. They’re more casual, don’t have a heel, and keep your feet warm.

When wearing dresses with Chelsea boots, I like pairing them with a boot sock, just for a little peek of sock above the boot. It gives it a bit of a softer look, and a nice transition from boot to leg.

You can wear this style of boot with lots of dresses – check out some more ideas HERE.

outfit links:

MERRICK WHITE COLLECTION DRESS | LEVI’S DENIM JACKET | TAN CHELSEA BOOTS

SIMILAR TAN SWEATER DRESS | AMAZON BOOT SOCKS | BLACK CHELSEA BOOTS | SIMILAR LEATHER JACKET

 

 

little black dress outfit for church in the winter
sheer tights with floral skirt

2. Wear black tights with a dress and boots

Boots and tights are a great option during the fall and winter when you need a little extra leg warmth.

You can wear tights and heels, but boots are a more practical option, especially when you’re going somewhere that might have snow or ice.

I chose a pair of black opaque tights in the first outfit, and a pair of black sheer tights in the second (you can get faux sheer ones that are lined with a lighter material). The sheer option is better if you want a less bottom-heavy look.

Also, if you’re wearing boots and tights and it’s super cold, add a pair of socks underneath for extra warmth!

outfit details:

SIMILAR PLAID WRAP COAT (PURPLE WRAP COAT HERE) |  KNEE LENGTH BLACK DRESS | BLACK OPAQUE AMAZON TIGHTS | SIMILAR BLOCK HEEL BLACK BOOTS

SIMILAR MOCK NECK SWEATER | SIMILAR STYLE MIDI SKIRT | SHEER AMAZON POLKA DOT TIGHTS | SIMILAR BLACK BLOCK HEEL ANKLE BOOTS

 

 

 

combat boots with a dress
How to wear a midi dress combat boots and sweater

3. Combat boots make for a fun, edgy outfit when combined with a dress

I don’t wear combat boots or lace up boots like this very often, but they are a fun combination with a dress if you want something that feels a little more edgy. You can wear them with a flowy feminine dress or a sweater dress — I’d just recommend doing something in a darker color or print, OR a heavier knit sweater fabric that balances the heaviness of black combat boots. You don’t want your outfit to feel bottom heavy!

In the second outfit, I wanted to balance the combat boots, so I put a black sweater over a floral dress and turned the dress into a skirt!

outfit details:

SIMILAR POLKA DOT DRESS | SIMILAR LACE UP COMBAT BOOTS 

SIMILAR BLACK CREW NECK SWEATER | SIMILAR FLORAL SKIRT | SIMILAR COMBAT BOOTS

 

 

 

riding boots with midi skirt

4. Play around with lengths with a knee-high boot

If you need some extra warmth, a taller boot is a great option. My favorites are a suede knee high or a leather riding boot.

Both work with shorter and longer dresses, as seen above!

outfit details from above:

ANTHROPOLOGIE SOMERSET SKIRT (pattern shown is sold out, similar HERE) | ABERCROMBIE SWEATER | LEATHER RIDING BOOTS  (similar HERE)

SIMILAR GRAY SWEATER DRESSSIMILAR GREEN COAT | SIMILAR SUEDE BOOTS | SIMILAR WOVEN CAMERA CROSSBODY BAG | AMAZON STRIPED BAG STRAP

 

 

 

over the knee boots with a dress
over the knee boots with plaid dress

5. Over the knee boots look amazing with a shorter dress

Over the knee boots are a great choice for longer or shorter dresses! I’m wearing a shorter dress here so there’s a gap in between the dress and the boots, but you could do a longer dress if you need more warmth.

And of course you can do tights in these outfits if you need more warmth.

outfit details:

SIMILAR BROWN FALL DRESS | AMAZON BUCKLE BELT | SIMILAR BLACK KNOTTED HEADBAND | SIMILAR OVER THE KNEE BOOTS

AMAZON PLAID DRESS | SIMILAR OVER THE KNEE BOOTS

 

 

Vince Camuto Maroon sweater dress
green dress with ankle boots

6. Tan block heel ankle boots are great with dresses

If you’ve worn a pair of nude or brown heels or sandals during the summer with your dresses, then a tan block heel ankle boot is the best choice during the fall and winter. It’s simple and feminine and doesn’t make your outfit feel bottom heavy.

You can wear with sweater dresses, flowy dresses, bodycon dresses, short or long dresses…they work with everything!

outfit details:

VINCE CAMUTO EXPOSED SEAM SWEATER DRESS | GOLD BELT  |  NEUTRAL STEVE MADDEN BLOCK HEEL BOOTIE

RENT THE RUNWAY MAXI DRESS (SIMILAR HERE) | BUDHA GIRL BRACELETS | SIMILAR TAN ANKLE BOOTS

 

 

I hope that’s helpful! Now go wear your dresses and boots together — you’ve got this.

 

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6 Comments

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  2. Hannah says:

    What color tights would work with tan Chelsea boots?

  3. For this most important thing is to select a dress which matches your boot style.

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  5. Your both dress are fabulus.

  6. Dixie C. Vanderbilt says:

    THis method seems good, I will try it and see. But can you tell me where to buy those boots? I want to wear them on the day i go to meet friend i met through the game pico park

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