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10 Best Dress Shoes with Jeans Combinations for Men
Gone are the days when jeans were strictly casual attire. With the right pair of dress shoes, you can elevate your denim game to create stylish outfits suitable for various occasions. Whether you’re aiming for smart-casual or a polished semi-formal look, pairing dress shoes with jeans can strike the perfect balance between comfort and sophistication.
In this guide, we’ll explore the 10 best dress shoes with jeans combinations for men to help you refine your style.
1. Oxford Shoes with Slim-Fit Dark Jeans
For a classic and refined look, pair oxford shoes with slim-fit dark-wash jeans. Oxfords, with their sleek design and closed lacing system, exude elegance and work seamlessly for semi-formal events.
How to Style:
- Pair black or brown oxfords with dark blue or black jeans.
- Add a crisp white shirt and a blazer for a polished look.
Occasions:
Perfect for office gatherings, dinner dates, or smart-casual events.
2. Brogue Shoes with Distressed Jeans
Brogue shoes, known for their perforated patterns, add texture and style to distressed jeans. This combination balances rugged and sophisticated elements.
How to Style:
- Choose tan or cognac brogues to contrast light-wash distressed jeans.
- Pair with a neutral sweater or a fitted polo shirt.
Occasions:
Great for casual outings, weekend brunches, or creative workplaces.
3. Loafers with Straight-Leg Jeans
Loafers are the ultimate slip-on dress shoes that pair beautifully with straight-leg jeans for a relaxed yet chic look.

How to Style:
- Opt for suede or leather loafers in black, brown, or navy.
- Wear with medium-wash jeans and a tucked-in shirt for a smart-casual vibe.
Occasions:
Ideal for summer outings, casual Fridays at work, or rooftop parties.
4. Derby Shoes with Black Jeans
Derby shoes are versatile dress shoes that pair effortlessly with black jeans for a sharp and modern aesthetic. Their open lacing design makes them slightly more casual than oxfords.
How to Style:
- Pair polished brown or black derby shoes with slim-fit black jeans.
- Add a turtleneck or a button-up shirt for a sleek outfit.
Occasions:
Perfect for evening dinners, casual weddings, or semi-formal gatherings.
5. Monk Straps with Tapered Jeans
Monk strap shoes, featuring unique buckle closures, offer a contemporary edge. Paired with tapered jeans, they create a standout look.
How to Style:
- Choose single or double monk straps in leather or suede.
- Pair them with dark-wash tapered jeans and a blazer for a modern outfit.
Occasions:
Great for date nights, cocktail parties, or upscale casual events.
6. Chelsea Boots with Skinny Jeans
Chelsea boots are a wardrobe staple, offering timeless style and versatility. When paired with skinny jeans, they create a sleek and streamlined silhouette.
How to Style:
- Go for black or brown Chelsea boots with dark skinny jeans.
- Add a leather jacket or overcoat for a chic winter look.
Occasions:
Ideal for evening outings, concerts, or winter gatherings.
7. Chukka Boots with Rolled-Up Jeans
Chukka boots are ankle-length dress shoes that pair perfectly with rolled-up jeans for a laid-back yet stylish look.
How to Style:
- Opt for suede chukka boots in neutral shades like beige or olive.
- Pair them with cuffed medium-wash jeans and a casual shirt.
Occasions:
Perfect for weekend road trips, casual meetups, or outdoor brunches.
8. Wingtip Shoes with Dark Indigo Jeans
Wingtip shoes, a subtype of brogues with distinctive "winged" toe designs, add a touch of vintage charm when paired with dark indigo jeans.
How to Style:
- Choose tan or oxblood wingtip shoes for contrast.
- Pair with slim-fit indigo jeans and a tweed blazer for a classic look.
Occasions:
Great for business-casual events or evening outings.
9. Cap-Toe Shoes with Faded Jeans
Cap-toe dress shoes, characterized by an extra piece of leather on the toe box, bring a subtle elegance to faded jeans.
How to Style:
- Choose brown or black cap-toe shoes with lightly faded jeans.
- Add a collared shirt and cardigan for a smart-casual outfit.
Occasions:
Perfect for casual office days or dinner with friends.
10. Suede Derby Shoes with Light-Wash Jeans
For a fresh and relaxed look, pair suede derby shoes with light-wash jeans. The texture of suede adds depth to this combination.
How to Style:
- Go for light-colored suede derby shoes, like tan or grey.
- Wear with light-wash jeans and a pastel sweater or casual blazer.
Occasions:
Great for spring outings, garden parties, or casual lunches.
Conclusion
Pairing jeans with dress shoes is an art that allows men to blend comfort and elegance seamlessly. From classic oxfords with slim-fit jeans to rugged chukka boots with rolled-up cuffs, the possibilities are endless. With these 10 best dress shoes with jeans combinations, you’ll be prepared for any occasion, whether it’s a casual outing or a semi-formal event. Experiment with different styles, and let your personal touch shine.
About InStyle Town
At InStyle Town, we believe every man deserves to look and feel stylish without sacrificing comfort. Our curated collection of Men’s Dress Shoes and Denim offers endless options to create perfect combinations for every occasion. Need more inspiration? Check out our other blogs on What Colors Go with Black and White Shoes and What Shorts Go Good with a Green Shirt to discover more styling ideas. Elevate your wardrobe today with InStyle Town!
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