How To Wear Ankle Boots With Dresses Over 50

How To Wear Ankle Boots With Dresses Over 50

Classic, versatile, and timeless: Ankle boots truly are a wardrobe essential. If you are someone who is new to the wonderful world of ankle-length boots, you may be wondering how to style them. Our sense of style certainly evolves over time, and we firmly believe that it’s never too late to experiment with your personal fashion.

From casual maxi dresses to professional office attire, here are the best ways to pair your ankle boots with any dress when you’re over 50.

Wearing Boots With Maxi Dresses

There is no better footwear for a fun, flowy maxi dress than a pair of ankle boots.

When investing in a new pair of ankle boots, we recommend opting for a neutral color such as black, brown, or tan. By keeping your go-to footwear a neutral color you maximize their versatility and are free to experiment with more color in other parts of your outfit. Maxi dresses are best worn in bright, fun colors after all.

Pairing Ankle Boots With Shorter Hems

Ankle boots aren’t just for long skirts and dresses. Show off those calves and pair your favorite ankle boots with a below-the-knee modest dress with a slightly higher hemline.

Tea Length Dresses and Ankle Boots

A lovely and classic dress style, tea-length dresses are those that fall about to the mid-calf, or somewhere between the ankle and the knee. This is the perfect length for showing off your ankle boots. This style of dress can be intimidating to some, as it can have the tendency to cut off the leg visually and make the wearer appear shorter.

A simple and stylish way to combat this effect is by pairing your tea-length dress with a pair of ankle boots. You can even add extra height and length to this look by opting for a pair of ankle boots with a slight heel. Add extra flair with a fashionable silky dress scarf.

Wearing Layers With Your Ankle Boots

Pairing your ankle boots with a cute dress is a great option for any season and, virtually, any weather or climate, as this look leaves lots of room for layering and dressing up or down depending on the occasion. In the cooler months of fall, you can layer a simple plain white t-shirt under a cute maxi or midi dress along with a pair of tights or leggings, a scarf, and your jacket. The winter is also a perfect time to wear those shorter dresses and skirts that you may be feeling hesitant to wear in the warmer months because now you can simply pair them with leggings or pants underneath.

To create a slimming and lengthening look, even when layering in the cooler months, we recommend wearing a pair of ankle boots with a slouchy and/or wide cuff. This will help accentuate and lengthen the calf area.

Wearing Ankle Boots in the Summer Months

In the spring, as the weather is warming up, you can still layer stylish fashion scarves, tunic tops, and flowy dresses. All of these billowy, flowing styles look extra summery and fashionable when elevated with a pair of ankle boots.

A cute and comfy cotton dress is the ultimate summer vibe for women and dress-wearers of all ages. Keep cool in your fun summery dress while still maintaining a mature and put-together look by pairing this style dress with your ankle boots. (We recommend that you opt for natural materials for your summer footwear, and try to stay away from plastic-based vinyl and faux leather to avoid your feet overheating.)

Business, Business-Casual, or Semi-Formal Attire

Ankle boots are truly versatile footwear. We love pairing ankle boots with professional dresses just as much as casual wear. You can just as easily pair your sleek leather ankle boots with a pencil skirt and a professional blouse as you can pair them with a stunning evening dress. For more formal occasions, we recommend staying away from embellishments such as straps or designs and opting for a more pointed toe-box.

We love pairing ankle boots with a pencil skirt or classic calf-length sheath dress for professional office attire. Top this look off with a tailored blazer. For a slightly more casual take on this business look, you can simply wear a slightly more casual dress under your blazer, such as a shift dress.

You don’t have to wear heels to look amazing in evening wear, either. Invest in a pair of classy ankle boots and you can rock them with any dress, at any age.


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