January 24, 2025
What Shoes to Wear with Jeans: The Ultimate Guide for Men
We’ve been there — you put together a picture-perfect outfit, but when it comes to picking out the shoes, things get tricky. What is it about matching men’s shoes with jeans that seems so simple but often feels impossible to get right? The reality is that your shoe choice matters — a lot. The wrong shoes can throw off your whole look, but the right ones can tie everything together seamlessly.
With a little bit of research, learning how to pick out the best shoes to wear with jeans will quickly become second nature. In this guide, we’re laying out 12 easy combinations and practical styling tips to help you nail your look every time, no matter the occasion.
1. Dress Boots
The best shoes to wear with jeans depend on your vibe and the event, but dress boots easily make the list. Boots, with their polished finish and structured design, are a great way to step up your jeans while keeping things versatile. Plus, they pair exceptionally well with straight-leg or slim-fit dark denim and a simple jacket or button-down shirt.
Styling Tip: Go for jeans with a clean hem that sits just above the boots or lightly grazes them. Throw on a tee, a nice blazer or leather jacket to add some edge.
2. Loafers
When it comes to effortlessly cool shoes to wear with jeans, loafers are the kind of footwear that instantly makes denim feel a little more elevated. They’re perfect for that smart-casual zone — like Sunday brunch, a casual day at the office or a relaxed dinner with family. Light- or medium-wash jeans work especially well here, and a slim or straight fit keeps the look sharp without feeling stiff.
Styling Tip: Roll up the hems of your jeans to create a clean, intentional vibe and stick to no-show socks (or go sockless if the weather allows). Pair loafers with a polo, a casual button-down or a tucked-in tee, depending on the occasion.
3. Chelsea Boots
Chelsea boots are a classic for a reason — they pair perfectly with any kind of denim and instantly add a touch of sophistication. Whether you’re going for dark-wash denim for a dressier look or lighter jeans for something more casual, Chelseas are functional and comfortable. Plus, they work especially well with slim-fit or straight-leg jeans that sit just at the top of the boot.
Styling Tip: Make sure your jeans are tailored or cropped to avoid bunching around the boots. Pair with a plain tee and a leather jacket for an effortlessly cool vibe, or go for a button-down shirt to dress it up a little. A wool coat can add a nice touch when the weather gets colder.
4. Lace-Up Sneakers
The quintessential cool guy combo, sneakers are not only some of the most comfortable shoes with jeans, they’re also incredibly versatile. From classic white sneakers to bold, trendy designs, the timeless lace-up can be dressed up or down to match any style of denim. This combo is perfect for anything the day throws your way, from running errands to heading to a casual lunch or meeting up with friends.
Styling Tip: Keep the look simple and clean by choosing sneakers that complement the rest of your outfit. Roll or crop your jeans slightly to show off the shoes, and stick to casual staples like a hoodie, graphic tee or a jacket to keep it laid-back and stylish.
5. Chukka Boots
If you’re in the market for casual shoes to wear with jeans, Chukka boots make jeans instantly look more put-together. They’re simple, comfortable, and work for pretty much any type of weather. Medium- or dark-wash jeans in a straight or slim fit look best, but you can also wear Chukka boots with a pair of gray or black jeans to dress them down a bit.
Styling Tip: Let the jeans sit right at the top of the boots, or give the hems a small roll to show off the shoe. To round out the outfit, throw on a flannel, crewneck sweater or a casual blazer.
6. White Sneakers
Yes, we’ve already covered sneakers with jeans. But let’s be real — white sneakers deserve their own honorary mention. A crisp pair of white sneakers is one of those forever-stylish shoes to wear with jeans that just works. Clean, simple and easy to style, white sneakers go well with literally any type of denim, whether it’s dark-wash, light-wash or distressed styles. Choose from lace-ups, slip-ons and more. They’re the go-to shoe for casual plans or days when you want to keep it easy without sacrificing style.
Styling Tip: Make sure your white sneakers are clean — it’s part of the look. Pair them with cropped or cuffed jeans to show them off, and keep it simple on top with a tee, hoodie or lightweight jacket. Want to level it up a little? A solid sweater or button-down shirt gets the job done without losing the laid-back feel.
7. Hiking Boots
Hiking boots aren’t just for the trails — they’re a solid choice when you need something rugged, reliable and comfortable. The trick here is to balance the sturdy look of the boots with the right pair of jeans. Straight-leg or dark-wash denim pairs best, keeping the outfit clean without feeling out of place or overly outdoorsy. Hiking boots are one of the best shoes that go with jeans on cooler days or when you’re expecting rain or snow.
Styling Tip: Stick to jeans that sit comfortably over the boots or try rolling the hems to keep the fabric from bunching on top of the shoe. Pair with a flannel, a quilted jacket or a simple hoodie to keep things relaxed and modern.
8. Retro Sneakers
Another pairing that never goes out of style, retro sneakers — like a classic pair of high-tops or low-profile lace-ups — are always a solid choice when it comes to versatile shoes to wear with jeans. They bring just a hint of nostalgia while still looking fresh and “just threw these on” cool. Go for slim or straight-leg jeans in light or medium washes to highlight the timelessness of these sneakers.
Styling Tip: Roll or crop the jeans slightly to show off the sneakers and keep the proportions clean. Pair with a vintage-inspired tee, crewneck sweatshirt or denim jacket to lean into the retro feel while keeping the look casual and stylish.
9. Lace-Up Boots
If you’re looking for all-time classic shoes that go with jeans, lace-up boots are always a reliable pick. They add structure and character to any outfit, perfect for casual plans or when you want something a bit sharper. Straight-leg or relaxed-fit jeans complement their sturdy design, but you can also opt for a wider leg if you want to incorporate more of a street-style vibe.
Styling Tip: Let the jeans fall naturally over the boots or roll the cuffs slightly to show off the laces. Add a utility jacket, a flannel or a cozy sweater to complete the outfit.
10. Espadrilles
Simple, stylish and incredibly comfortable, there’s every reason to fall in love with espadrilles. They’re an easy choice for any kind of denim but pair best with relaxed-fit or straight-leg jeans, adding an easygoing yet elevated element to your outfit. Perfect for warm weather or casual summer plans, they’re particularly good shoes to wear with jeans that come in a light-wash or are slightly cropped.
Styling Tip: Go sockless or use no-show socks. Pair with an untucked linen shirt, a simple tee or a lightweight sweater. For warm seasons, add sunglasses or a woven belt. In cooler weather, pair with a button-up or a flannel for a laid-back look.
11. Slip-On Sneakers
Slip-on sneakers are the ultimate low-effort, high-reward choice when it comes to shoes to wear with jeans. They’re comfortable, easy to wear and add just the right amount of no-effort cool to your outfit. Whether you’re running errands, grabbing coffee or hanging out with friends, they work with everything from slim- to relaxed-fit jeans without overcomplicating things.
Styling Tip: Roll your jeans slightly to show off the sneakers, or let the hem sit just above. Throw on a hoodie, a tee or a lightweight jacket to keep the whole look casual and charming.
12. Lug Boots
Jeans are great for when you want to dress informal and easy-going, but the shoes you choose can instantly elevate your look. Lug boots are a perfect example — they bring a refined touch while keeping the outfit approachable. To pull it off, straight-leg or slim-fit jeans work best, particularly if you pair them with a button-down shirt or a crisp crewneck sweater.
Styling Tip: Make sure your jeans are tailored to sit right at the top of the boots or just graze them. Add a belt that matches the tone of your boots, and layer with a wool coat or blazer if the weather calls for it.
The Do’s and Don’ts of Wearing Men’s Shoes With Jeans
Now that you know what shoes go best with jeans, get to know these quick guiding principles to ensure your outfit always looks on point. Here’s how to get it right every time:
Do’s
- Match the style of your shoes to the tone of your outfit. Choose casual shoes for relaxed looks, dressier options for more refined outfits.
- Keep jeans tailored or cuffed to hit the right length, especially with boots or high-tops.
- Stick to well-maintained shoes. Scuffed or worn-out pairs can throw off an otherwise great outfit.
- Slim or straight-leg jeans pair best with most shoe styles because they offer unmatched balance and versatility.
- Use accessories like belts or baseball caps to tie your outfit together. In the case of leather shoes, match your belt to the tone of your shoes for a cohesive look.
- Experiment with textures. Suede boots, leather sneakers or canvas slip-ons can add visual interest to your outfit.
- Coordinate colors subtly. Neutral shoes are versatile, but a pop of color can elevate a simple outfit.
Don’ts
- Let jeans bunch up or drag over your shoes. It looks unkempt and messy.
- Pair overly formal shoes with distressed or ripped denim. This creates a clash that feels out of place.
- Combine baggy jeans with sleek or fitted shoes. They make the outfit feel mismatched and unbalanced.
- Ignore proportions. Chunky shoes need jeans with a bit of room, while slim shoes work better with fitted denim.
- Overload your outfit with too many bold elements. Let only one piece take the spotlight.
- Skip socks with shoes that clearly need them. No one wants to see dress shoes or boots without socks.
- Pair statement shoes with an overly busy pattern. They’ll compete for attention and make the outfit feel chaotic.
- Forget to consider the occasion. Some combinations may stand out (in the wrong way) in certain settings.
Wear TOMS. Wear Good.
The right pair of shoes can take your jeans from casual to dressy, and anywhere in between. Whether you’re choosing classic styles like sneakers and boots or want something more unique, like espadrilles or dress shoes, we’ve got you covered. When you shop TOMS, you can step up in style while also making a difference.
Shop our collection of men’s shoes and find your perfect pair today.