Men’s Fashion: How to Dress Chic and Comfortably While Traveling

It’s a constant struggle between comfort and style in the domain of men’s fashion. How do you get the best of both worlds, especially when facing the challenges of travel? On the road, you’ve got less control over the environment and more variables to contend with, making it all the more difficult to balance style and comfort at once.

But after years of trial and error - plus some help from the fashion industry - we think we’ve cracked the code on men’s travel fashion. Here’s our definitive guide to dressing with style while staying comfortable and ready for the challenges ahead.

Basics and Essentials

Every great outfit starts with a few basics, and dressing for the road is no different. If you’ve been ignoring the fundamentals of style for years, this is the perfect time to go back to the drawing board and finally invest in these essentials.

For starters, undergarments can’t be underestimated in their ability to change how you feel during long-range expeditions. When traveling, your undershirts, boxer briefs, and socks account for a lot of comfort - or lack thereof.

Knowing this, prioritize fit, flexibility, breathability, and longevity when shopping for undergarments from top to bottom. Spend more if you must to get the best materials available in each category.

This goes for t-shirts and tanks as well - you never know when you might need to wear a basic tee when the weather heats up.

Layers for Any Season

Real style starts to develop once you add more layers to the foundation, and this largely depends on the conditions you expect when traveling.

Ideally, you’ll have a few lightweight yet resilient layers to work with, starting with button-down shirts and sweatshirts in casual formats. No need for super formal spread-collar dress shirts and ties here. The tops should be wrinkle-proof, offer some protection and warmth, and also match in terms of color and print.

You can quickly tell if a shirt is built for travel by its weight, fit, and versatility. High-end dress shirts look nice when properly ironed and starched, but aren’t optimal for journeys in suitcases. Find tops that are ideal for grab-and-go outfit assembly and offer the greatest amount of flexibility with the rest of your wardrobe.

From there, it’s all about adding warmth and coverage to that foundation, whether that means wearing chore coats, flannels, denim jackets, windbreakers, or whatever else keeps you warm and comfy. Bulk is the enemy here; only wear oversized jackets as an absolute necessity on the road.

Also, get familiar with functional accessories like hats, scarves, gloves, and others. These add big style points and also keep you toasty in unexpected conditions.

Travel-Focused Footwear

The age-old question persists: what shoes are best for travel while still looking stylish? Loafers seem like a good pick for their laceless format, but they may be too formal for most men getting from A to B.

On the other hand, flip-flops are far too flimsy and don’t offer the protection you need, even in warmer climates. Where is the middle ground here?

The answer is to find durable, versatile shoes with closed toes, resistant materials, and a dash of style. They might not be the most eye-catching kicks, but you’ll be happy you have them for the long road ahead.

Look for lightweight hiking shoes, for instance, that feature slip resistance and some extra ventilation. Some styles look more like sneakers so that you don’t look flat-footed for a photo op.

Try to avoid shoes that need constant polishing and upkeep, and seek out a travel-oriented alternative in a similar vein.

If you're attending a destination wedding, consider wedding shoes for men from Del Toro Shoes for a blend of elegance and comfort during your travels.

Versatile Travel Pants

Once you have a set of reliable basics, plus shoes and shirts, it’s time to shift focus to pants. This tends to be the most challenging part of travel wear for guys.

The problem is that most men are stuck in their ways when it comes to pants, and are not willing to think beyond their standard denim or business-casual khakis. This leads to pants problems like bunching, overheating, and a general lack of flexibility and comfort (not to mention style).

Therefore, more guys should be open to the idea of mens travel pants designed for that specific purpose. These pants tend to be ergonomically constructed, meaning they work with the human body rather than against it.

These pants are also typically made with materials like nylon and other synthetic fabrics, meaning they’re far more flexible and resistant to water, oil, and dirt. They’re also way comfier and contain plenty of extra storage space for accessories and gear. 

Your Travel Wardrobe Made Easy

We could all dress better for travel, both from a comfort and style standpoint. These tips should help any man level up his travel wear game and prepare for the road ahead. 


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