Dress With Boots - How to Style It - Merrick's Art (2024)

Dress With Boots - How to Style It - Merrick's Art (1)

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.

Dress With Boots - How to Style It - Merrick's Art (2)

Dress With Boots - How to Style It - Merrick's Art (3)

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

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

Dress With Boots - How to Style It - Merrick's Art (6)

Dress With Boots - How to Style It - Merrick's Art (7)

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

Dress With Boots - How to Style It - Merrick's Art (8)

Dress With Boots - How to Style It - Merrick's Art (9)

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 DRESS |SIMILAR GREEN COAT | SIMILAR SUEDE BOOTS | SIMILAR WOVEN CAMERA CROSSBODY BAG | AMAZON STRIPED BAG STRAP

Dress With Boots - How to Style It - Merrick's Art (10)

Dress With Boots - How to Style It - Merrick's Art (11)

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

Dress With Boots - How to Style It - Merrick's Art (12)

Dress With Boots - How to Style It - Merrick's Art (13)

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.

If You Liked This Post, You Might Also Like:

  • How to Wear a Dress in Winter

  • Straight Leg Jeans and Ankle Boots

  • Winter Dress Outfits

Dress With Boots - How to Style It - Merrick's Art (2024)

FAQs

How to pair a dress with boots? ›

If you have a petite frame, opt for shorter dresses to elongate your legs and pair them with ankle boots. On the other hand, if you are tall, you can get away with wearing longer dresses with knee-high or over-the-knee boots for a more dramatic look.

How to wear ankle boots over 60? ›

Try a trusty ankle boot.

"Pair with a bootleg cut pant and cropped jacket for a classic look, or with leggings and a long blazer or sweater coat for a more casual, layered effect," she suggests. You could also pair the style with a long skirt or dress.

Can I wear boots with a dressy dress? ›

Pay attention to the length of your dress. Ankle boots work well with knee-length or midi dresses, while knee-high boots can pair nicely with longer hemlines. Avoid styles that are too short or too revealing for a professional setting. Choose a simple and classic dress style.

Are dresses and boots still in fashion? ›

With miniskirts, they look inherently cool and work to balance out the short hemline. Truly, dresses and knee-high boots make a perfect pairing, and I'm not the only one who thinks so.

What sort of boots to wear with a dress? ›

Knee-high boots and dresses are a match made in heaven. Wear them with a mini dress, and they create a flattering look that accentuates your legs, but pair them with a midi dress, and you'll look like you've walked straight off the runway!

Are ankle boots with dresses in style? ›

Opt for ankle boots with a low heel or a flat sole to keep the focus on the dress. Or, add a simple heeled pair for a little height. Add a denim jacket or a leather moto jacket to add a touch of edge. Remember, the key to pairing ankle boots with skirts and dresses is to create a balanced and harmonious look.

Is 40 too old to wear over-the-knee boots? ›

Fashion has no age limit. It's for both old and young. You can be over 40 or 50 and still look beautiful with some rules that guide styling Knee-high-boots. Being versatile earns Knee-high boots recognition among people in a different places.

Do ankle boots go over or under jeans? ›

If your boot shaft is tall, you can tuck your pants UNDER the boots. If your boot is ankle length, just make sure the hem of the jeans meets the top of the boot shaft.

What length pants to wear with ankle boots? ›

So here's the quick and dirty answer. Your pants should hit right above your ankle boots. Any longer and you get that awkward bunching and scrunching.

What makes a boot dressy? ›

Dress boots will be sleeker, sharper, sometimes with a squared-off chisel toe. They're usually made from full-grain leather, rather than suede or nubuck, and the soles will be leather (or discreet rubber in a pinch) – never crepe or thick, chunky rubber.

What kind of dress pants can you wear with boots? ›

When it comes to wearing boots to work I personally prefer them with full-length pants. The pants can be wide-leg, flare, or full-length straight. Ankle pants are great, but I think they look best with a shoe that shows some skin like a ballet flat, pump or loafer.

Should you wear boots with a dress to a wedding? ›

Yes, ankle boots are a stylish option to wear to a wedding with casual dresses and black dresses alike. Unlike knee-length boots or more heavy-duty snow boots, some ankle boots are formal enough for most ceremonies. If you're headed to a fall or spring wedding, a pair of Timberlands will keep your feet warm and dry.

Can you wear boots with a midi dress? ›

Keeping up with this trend-led look midi dresses and ankle boots are effortlessly stylish and an outfit that you can wear with confidence. Chunky boots are this season's must-have footwear for their fashionable look and another perfect way to style your midi dress.

Should I wear tights with a dress and boots? ›

Can you wear tights with open-toed shoes or boots? Yes! Wearing open-toed shoes doesn't need to bring the feeling of dread or a last-minute dash to get your nails painted – instead, we suggest throwing on a pair of your favourite tights with your dress!

Do you wear tights with dress and boots? ›

While you may feel sad to say goodbye to summer, autumn brings with it a whole new range of outfits that you can wear. One of the best outfit combinations for the colder seasons of the year are dresses, tights, and boots.

Can I wear long boots with a dress? ›

Wear your knee-high boots with a dress for a feminine and modern look. Knee-high boots will instantly elevate your outfit, no matter how casual your dress is. Try wearing heeled knee-high boots under a midi dress in the daytime, or style a pair of flat knee-highs with a mini dress for a sophisticated evening look.

Should I tuck dress pants into boots? ›

Just don't go too short, or you'll end up with an unsightly high-water look. One more thing: guys, if you're wearing something dressier than jeans, such as slacks, never, ever tuck your pants into boots! Just trust us on this one.

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