14 Ways To Make Comfortable Shoes Look Stylish After 50

Turning 50 doesn’t mean you have to sacrifice style for comfort, especially when it comes to your footwear. With the right approach, it’s entirely possible to make comfortable shoes look chic and fashionable.

Be it choosing the right design or pairing them with the perfect outfit, here are 14 creative ways to ensure your comfort doesn’t compromise your style.

Explore these innovative and practical tips to elevate your shoe game and step out with confidence and flair, no matter the occasion or season.

1. Sneakers with Tailored Trousers

Sneakers paired with tailored trousers create an elegant yet comfortable look. The sleek lines of the trousers complement the casual vibe of the sneakers, offering a fresh and modern style. Opt for sneakers in neutral colors to maintain a polished appearance.

Adding a blazer or a structured jacket can elevate the ensemble, making it suitable for casual and semi-formal settings.

Accessorize with a chic handbag or statement jewelry to enhance the overall look without overshadowing the simplicity of the sneakers.

2. Loafers with Midi Skirts

Loafers and midi skirts are a match made in heaven for chic comfort. The timeless appeal of loafers, combined with the feminine silhouette of a midi skirt, creates a look that is both graceful and relaxed. Choose loafers in a bold color for added flair.

Midi skirts offer a flattering length that suits a wide range of body types, making them ideal for those seeking style without compromising comfort.

Consider adding a light sweater or blouse to complete the outfit, enhancing warmth and style.

3. Ankle Boots with Skinny Jeans

Ankle boots and skinny jeans are a dynamic duo that never goes out of style. This pair combines comfort with a touch of edge, perfect for those looking to make a fashion statement.

Select boots with a slight heel for added height and sophistication. When paired with a cozy knit sweater or a tailored coat, this ensemble becomes a go-to outfit for cooler weather. The streamlined look of skinny jeans enhances the chic appeal of the boots.

Experiment with different textures and colors to add depth and interest to your outfit, while maintaining a cohesive and polished look

4. Ballet Flats with Wide-Leg Pants

Ballet flats paired with wide-leg pants offer a combination of elegance and ease. The comfortable flats complement the flowy nature of the pants, providing a silhouette that moves beautifully.

Opt for flats in a vibrant color to add a pop of interest. Wide-leg pants can be stylish and forgiving, making them an excellent choice for a sophisticated yet laid-back look.

This ensemble can easily transition from a casual day out to an evening event. Top the look with a fitted blouse or a tucked-in shirt to maintain balance and accentuate your waistline.

5. Espadrilles with Sundresses

Espadrilles and sundresses are synonymous with summer style. This pairing embodies the essence of comfort and breezy elegance. Choose espadrilles with a wedge heel for a bit of lift without sacrificing comfort.

Sundresses in light fabrics provide a relaxed vibe, perfect for warm weather adventures. The simplicity of the espadrilles complements the playful nature of the dress, creating a harmonious and stylish ensemble.

Add a wide-brimmed hat or a straw bag to enhance the summery feel, making this combination ideal for vacations or leisurely outings.

6. Mules with Cropped Pants

Mules and cropped pants are a stylish pairing that exudes sophistication and comfort. The slip-on nature of mules makes them ideal for effortless wear, while cropped pants provide a contemporary silhouette.

Choose mules in a metallic finish for a touch of glamour. Cropped pants allow for versatility in style, perfect for showcasing the elegance of mules. This combination is suitable for casual and upscale settings.

Enhance the look with a crisp button-down shirt or a modern blouse, adding layers or accessories to suit the occasion and personal taste.

7. Platforms with A-Line Dresses

Platforms paired with A-line dresses make for a bold and stylish statement. The added height from platforms offers elegance without compromising comfort. Opt for platforms in a classic color to ensure versatility.

A-line dresses are flattering and timeless, offering a feminine silhouette that pairs beautifully with platforms. This ensemble is perfect for casual and formal occasions, providing flexibility in dressing up or down.

Complete the look with a statement belt or eye-catching accessories to draw attention and add personal flair to this chic combination.

8. Oxfords with Culottes

Oxfords and culottes bring together vintage charm and modern style. The structured nature of oxfords pairs beautifully with the relaxed fit of culottes, creating an ensemble that is unique and comfortable.

Choose oxfords in a patent finish for a touch of sophistication that elevates casual culottes. This pairing opens up endless styling possibilities, suitable for various occasions and settings.

Layer with a fitted blazer or a cozy sweater to add dimension and warmth, making this combination appealing for transitional seasons.

9. Slip-Ons with Jumpsuits

Slip-ons and jumpsuits are a match made in heaven for ease and style. The nature of slip-ons complements the all-in-one appeal of jumpsuits, making it a go-to outfit for those on the move.

Opt for slip-ons in a bold pattern to add interest and contrast to the jumpsuit. This combination is perfect for travel or busy days, offering comfort without sacrificing sophistication.

Accessorize with a statement necklace or a stylish handbag to enhance the ensemble, creating a look that is practical and fashionable.

10. Wedges with Maxi Dresses

Wedges and maxi dresses are synonymous with elegant comfort. The stability of wedges pairs with the flowing nature of maxi dresses, providing a look that is graceful and chic.

Select wedges in a neutral tone to complement the often vibrant patterns of maxi dresses, ensuring a cohesive and stylish outfit. This pairing is ideal for outdoor events or casual gatherings.

Add a lightweight scarf or bold earrings to complete the look, offering additional layers of interest and personality to this effortless combination.

11. Clogs with Denim Skirts

Clogs paired with denim skirts create a nostalgic yet trendy look. The chunky nature of clogs provides a retro flair that complements the casual vibe of denim skirts.

Opt for clogs in a natural wood finish for an authentic feel. Denim skirts offer comfort, making them a staple in any wardrobe. This pairing is perfect for casual outings or relaxed weekends.

Top off the look with a simple tee or a classic blouse, adding a playful scarf or hat for a touch of fun and creativity.

12. Sandals with Linen Pants

Sandals and linen pants are the epitome of breezy comfort. Choose sandals in a metallic or embellished design to add a touch of glamour to the ensemble.

This combination is ideal for warm weather, offering a cool and comfortable option.

Pair with a lightweight top or a breezy blouse, accessorized with layered necklaces or a sun hat to enhance the relaxed vibe of this outfit.

13. Pumps with Pencil Skirts

Pumps and pencil skirts are a classic combination that exudes elegance and professionalism. The sleek design of pumps enhances the sophisticated silhouette of pencil skirts, creating a timeless look.

Opt for pumps in a vibrant color or pattern to add a modern twist to this classic pairing. This ensemble is ideal for office wear or formal events, offering style and grace.

Complete the look with a tailored blouse or a smart blazer, accessorized with subtle jewelry for a polished and confident appearance.

14. Derby Shoes with Shift Dresses

Derby shoes paired with shift dresses offer a blend of menswear-inspired style and feminine flair. The structured look of derby shoes complements the simple elegance of shift dresses, creating a unique and fashionable ensemble.

Select derby shoes in a bold color to add an unexpected twist to the outfit. This pairing is perfect for those who appreciate a touch of androgyny in their style.

Enhance the look with a statement belt or bold accessories, ensuring a cohesive and eye-catching appearance that stands out in any setting.