January 31, 2025
From Dressy to Casual: 5 Shoes Every Man Should Own
Whether it’s a last-minute scramble for a big presentation at work or digging through your closet for the right pair of shoes for tonight’s date, not having the right pair can leave you feeling unprepared and stressed when it matters most. That’s why every man needs a selection of go-to shoes that work for anything and everything.
That’s why we’ve put together this lineup of the most essential shoes for guys, each category hand-selected to fit easily into your everyday life — from casual weekends to more put-together moments.
Stay put, because in this guide we’re going over the top 5 shoes every man should own, what makes each pair a wardrobe staple, and quick styling tips for how to wear them.
1. Loafers
Loafers are a non-negotiable when it comes to a well-rounded shoe collection, and for good reason. They’re at the top of the list of shoes men should own because of how versatile they are, striking the perfect balance between laid-back and dressed-up. Whether you’re heading to the office, meeting friends for brunch or attending a semi-formal event, loafers bring an elegant touch to your look without feeling over the top.
Pair leather loafers with slim-fit slacks and a button-down if you need to look clean and professional. Or, opt for a sleek black loafer with a monochrome outfit for a night out or a lunch date.
Do’s
- Match your belt with your loafers for a coordinated look.
- Keep the leather or suede conditioned to extend their lifespan.
- Experiment with no-show socks during warmer months.
Don’ts
- Pair loafers with baggy or overly distressed jeans — they’ll lose their elegant effect.
- Wear loafers with formal suits meant for lace-ups like Oxfords.
- Neglect cleaning — dust and scuffs can take them from stylish to sloppy fast.
2. Sneakers
We know, we know — this is a huge category. But that’s the beauty of men’s sneakers! There are endless variations in design, style and more so you can find the perfect pair. From sporty casual slip-ons to dress casual sneakers, you’ll find it all. Not to mention sneakers are versatile, comfortable and always stylish.
When it comes to styling, sneakers give you lots of room to experiment. A clean, white sneaker looks effortlessly cool with slim jeans and a crisp t-shirt. For something a bit bolder, a sneaker with pops of color or texture can add personality to neutral outfits. Sneakers can even be dressed up for certain work environments — for example, you can opt for minimalist leather sneakers with chinos and a crewneck sweater for a dressy yet casual dinner date. The key is knowing how to choose the right pair for the right setting.
Do’s
- Rotate your sneakers — wearing the same pair day in and day out can wear them out faster.
- Clean them regularly, especially the soles, to keep them looking fresh.
- Pair clean, neutral sneakers with casual suits for an unexpected yet modern twist.
Don’ts
- Wear beat-up sneakers to work or formal events, even if they’re your favorite pair.
- Skip the socks. Invisible socks are fine, but going completely sockless can lead to odor and wear issues.
- Overlook proper storage. Tossing them in a heap at the back of your closet can lead to creases and misshaping.
3. Boots
Whether you live somewhere warm or cold, boots are some of the most versatile men’s shoes you can own. A good pair of boots is stylish and functional, perfect for elevating any outfit, navigating cooler weather or stepping into a smart-casual event.
Two styles you’ll want to focus on in this category are Chelsea boots and chukkas. Chelsea boots, with their streamlined design and elastic side panels, are your go-to for an elegant yet effortless look. They go great with slim-fit jeans, a crisp shirt and even a tailored blazer. Chukkas, on the other hand, are more laid-back with their ankle-height design and lace-up style. They’re perfect for casual occasions, like a lunch date or a relaxed office setting, and work well with chinos or dark denim.
Do’s
- Choose high-quality materials like leather or suede for durability and style.
- Maintain them properly — polish leather boots regularly and treat suede with a protective spray.
- Pair Chelsea boots with slim or tapered pants to highlight their design.
- Wear chukkas with textured fabrics like flannel or corduroy for a balanced and stylish look.
Don’ts
- Skip weatherproofing, especially with suede. Wet conditions can ruin them fast.
- Let them get too scuffed or worn — proper care keeps them looking sharp.
- Wear baggy pants that cover or bunch around the boots — it throws off the overall look.
4. Dress Casual Shoes
Another must-have shoe, men’s dress casual shoes are a timeless essential that every wardrobe needs. Designed for more formal events and professional moments, this shoe type for guys is indispensable for events like weddings, job interviews or important meetings.
For formal settings, go for structured classic Oxfords in black or brown, and, for slightly less formal occasions, lace-up shoes are a great choice. Lace-ups are a staple because they add refinement to your wardrobe, so while you might not need to wear them every day, they’ll save you when the occasion calls for something more elevated.
Do’s
- Keep them polished and conditioned to maintain their appearance and prevent cracking.
- Use a proper shoehorn to avoid damaging the back when putting them on.
- Pair them with tailored trousers or suits for a classic look.
Don’ts
- Wear them with casual outfits like shorts or baggy jeans — they’re meant for dressier styling.
- Lace-ups are one of those shoes men should have in case of a special occasion, but don’t neglect cleaning after each wear — water spots and salt can damage the leather.
- Forget to store them properly. Shoe trees, for example, help maintain their shape and keep them looking like new.
5. Espadrilles or Alpargatas
Some days call for more casual footwear, which means we couldn’t leave espadrilles or alpargatas off the list of men’s essential shoes. Light, breathable and with a touch of old-world flair, these shoes are perfect for warmer weather and laid-back occasions.
Espadrilles, alpargatas and slip-ons are perfect for vacations, casual summer days and outdoor gatherings, like daytime weddings and neighborhood BBQs. Pair them with linen shorts and a button-down for a cool summer look, or wear them with rolled chinos, a simple t-shirt and a light-colored blazer for something more refined yet casual.
While they’re great for casual settings, espadrilles aren’t built for heavy-duty wear or formal events, so knowing when to pull them out is key. They’re best reserved for warm-weather months and relaxed environments where comfort and style are the priority.
Do’s
- Keep them clean and free of stains by spot-cleaning the fabric regularly.
- Pair them with breathable, lightweight fabrics like linen or cotton.
- Let them air out after wearing to prevent odors and keep them fresh.
Don’ts
- Wear them in wet conditions — the woven soles aren’t designed to handle water and can get damaged.
- Wear them with socks.
- Treat them as athletic or all-purpose shoes — they’re meant for casual comfort, not heavy use.
Wear TOMS. Wear Good.
Now that you know the most essential categories of shoes all men should have, it’s time to pick the pairs that best match your style. From classics that elevate your wardrobe to everyday staples that can handle whatever the day brings, shopping for the right shoe types for guys is all about choosing pieces that work for your lifestyle.
At TOMS, we’re proud to create shoes that do more than complete your look. Every pair you choose helps us give back and support communities that need it most. Learn more about how you can have an impact.
Explore our men’s shoes collection and find the perfect pair today!