The Chicago Clothing Brand Making Comfortable Travel Cool

November 9, 2026 Vacationer Staff

Why clever Chicago label Mugsy could become a travel wardrobe favorite for men and gender-nonbinary Vacationers who want to look stylish without spending their journeys squeezed into uncomfortable clothes.

We love discovering a clothing brand that understands one of travel’s great frustrations: looking good and staying comfortable don’t always go together. Jeans can feel restrictive on a long-haul flight, chinos can become uncomfortable after hours of sightseeing, and even the smartest-looking trousers can leave you longing for something with an elastic waistband.

Enter Mugsy, the Chicago-born clothing company that has built its reputation on challenging the idea that men have to sacrifice comfort for style. Its philosophy is refreshingly straightforward: clothes should look good, feel fantastic and allow you to get on with your life.

For men and gender-nonbinary travelers in particular, that proposition has considerable appeal. Whether navigating an airport, exploring a new city, spending an afternoon at the beach or heading straight from sightseeing to dinner, Mugsy’s combination of relaxed fabrics and contemporary silhouettes offers an appealing alternative to conventional menswear.

Mugsy was founded by Chicago entrepreneur Leo Tropeano, whose journey into fashion began with a rather familiar wardrobe dilemma.

After graduating from college, Tropeano moved to New York to work in public accounting. He wanted to upgrade his style, starting with a better pair of jeans. But he discovered that the slimmer, more fashionable denim available at the time was often uncomfortably tight. Meanwhile, his old, looser-fitting jeans weren’t doing his appearance any favors. Rather than accept the compromise, he decided to create something better.

Tropeano began working with apparel specialists, experimenting with fabrics and testing thousands of materials to find a combination that delivered a contemporary, flattering silhouette without restricting movement. After initially testing the idea through Kickstarter, he returned to the drawing board, refined the product and launched Mugsy in Chicago in November 2016.

The original ambition was to deliver three things: supreme comfort, a clean and stylish fit, and room where men actually need it. That customer-first philosophy remains central to the company. What began as a denim business has grown into a broader clothing collection, including trousers, shorts, shirts, knitwear, and other casual wardrobe essentials.

Five Mugsy styles worth packing

Traditional denim is rigid and lacks the give needed when sitting in a cramped airline seat for hours. Waistbands can dig into your stomach, especially when you experience natural bloating and pressure changes at altitude. Tight jeans or restrictive skinny jeans can hamper blood flow in your legs and lower body. Combined with prolonged sitting, restricted circulation can increase your risk of discomfort, swollen ankles, and deep vein thrombosis (DVT, or blood clots).

The real test of travel clothing is how it performs beyond the mirror. Does it remain comfortable after sitting on a plane for eight hours? Can you walk several miles without feeling restricted? Does it look sufficiently polished for a restaurant or an evening out? The five pieces we’re trying offer an interesting cross-section of Mugsy’s approach, from warm-weather casualwear to versatile everyday denim.

Beachwoods – ultimate relaxation

The comfort of sweatpants, the look of proper trousers. The Beachwoods are made from soft, durable brushed twill with plenty of stretch to keep you moving comfortably, wherever the day takes you. A relaxed fit, easy drawstring waist and handy patch pockets make them a natural choice for everything from long flights and sightseeing to casual dinners. Pair them with a tee and sneakers or dress them up a little — these pants are ready for the journey. These khaki twill drawstring shorts are a particularly appealing warm-weather option. They have a seven-inch inseam, oversized patch pockets and a button-and-drawstring waistband. The cotton and spandex brushed twill gives them flexibility without losing the appearance of proper shorts.

Fultons – the everyday all-rounder

Fultons are one of Mugsy’s signature denim offerings and a particularly good starting point for anyone curious about the brand. The cotton-rich denim blend incorporates polyester, rayon and spandex, giving it the flexibility and softness that underpin the Mugsy concept. The naturally faded blue wash is versatile enough for daytime exploring, travel days and evenings out. The appeal is that you get the familiar appearance of classic jeans without the traditional stiffness.

Some stretch jeans can feel thin, lose their shape or look more like athletic clothing than proper denim. Mugsy’s proposition is to preserve the recognizable appearance of jeans while making them considerably more forgiving.

Daytonas – a little vintage attitude

The Daytonas bring a lighter, vintage-washed blue to the collection. They’re designed to look contemporary and flattering while retaining the considerable stretch of Mugsy’s denim. These work particularly well for city breaks, casual dinners, and weekend adventures. They have a slightly more relaxed, youthful feel than traditional dark denim and look great with sneakers, a casual shirt, or a lightweight sweater.

Mugsy’s signature denim uses a proprietary cotton-rich blend incorporating polyester, rayon, and spandex. The company says it has spent a decade refining its fabric, using more spandex than many conventional stretch-denim alternatives to improve flexibility while retaining the feel and appearance of denim.

Squid Inks – the versatile black essential

Black jeans are among the hardest-working pieces in any travel wardrobe. Mugsy’s Squid Inks offer a true monochromatic black finish, with the same proprietary stretch-denim construction as its other classic jeans. The black-on-black appearance makes them especially easy to dress up or down. Wear them with sneakers and a tee during the day, then switch to a smarter shirt and boots for dinner. The relaxed Casual version offers additional room through the hips and thighs, while the standard and tapered versions provide different silhouettes.

Toasties – the comfort-focused addition

Toasties are a cozy addition to a travel wardrobe, especially for cooler weather, long journeys and relaxed evenings. They might be too warm for the plane, but they’re definitely our pick for winter warmth when you’re out and about, especially if that means a road trip and checking into your Vrbo chalet or cabin. I’d be interested in assessing their softness, warmth, weight and how easily they layer with other pieces.

Why Mugsy makes sense for LGBTQ+ travelers

For many LGBTQ+ travelers, clothing is a form of personal expression. Some prefer traditionally masculine silhouettes; others enjoy playing with proportions or choosing pieces that feel less restrictive than conventional menswear. Gender-nonbinary travelers may also appreciate clothing that offers flexible fit and styling without assuming how someone should dress.

Mugsy markets its collection primarily as men’s clothing. However, its emphasis on comfort, movement, and contemporary silhouettes could make it an appealing discovery for a broader audience. There are several reasons:

Comfort without compromise: Stretch fabrics and softer materials can make a significant difference when traveling, particularly on long flights, road trips and days spent walking.
Less restrictive fits: Mugsy offers several silhouettes, including its Classic Mugsy, Slim Tapered and Relaxed Casual fits. That choice can be useful for people who prefer more room through the hips and thighs or simply dislike restrictive clothing.
Easy personal styling: Black jeans, vintage denim and khaki shorts are versatile foundations. They can be styled traditionally, or mixed with more expressive accessories, footwear and tops.
Clothing that transitions: A good pair of jeans shouldn’t be restricted to one occasion. The ability to go from a daytime excursion to a bar, restaurant or evening event without changing outfits is particularly useful when traveling.

Ultimately, the appeal is not about dressing according to a particular identity. It’s about having clothes that allow people to feel comfortable and confident in their own presentation.

A Chicago brand with a growing following

Mugsy has grown considerably since its 2016 launch. What began as a relatively focused denim proposition has become a broader menswear business, with a substantial online following and physical retail presence.

Its success also reflects a wider shift in menswear. Consumers increasingly want clothing that works with their lifestyles rather than clothing that requires them to adapt to it. The old distinction between smart clothes and comfortable clothes is becoming less relevant.

Mugsy’s approach hasn’t abandoned recognizable classics. Jeans still look like jeans, shorts still look like shorts, and the silhouettes remain accessible. The innovation is largely in how the clothes feel and move. For anyone who has ever cringed at the thought of wearing tracksuit pants on a long-haul flight, so worn jeans, and then had to peel them off immediately after arriving at a hotel, this label is for you.