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Fall Fashion Essentials for Male Entrepreneurs

Home Business Magazine Online

As an entrepreneur, your first impression is important. An attractive, high-quality wardrobe is not only a great way to boost positivity in your first impressions, but you’ll also feel more confident as you move through your daily business. With the temperature cooling down and the crisp mornings greeting your new days, you’re probably getting warmer attire hung and ready in your closet. With every season change, it’s always a good idea to freshen up your wardrobe with new staple pieces to elevate your style and boost your confidence. If you’re seeking the latest Fall Fashion Essentials, we’ve got your covered. Below is a list of high-quality, professional and comfortable fashions that will elevate your fall wardrobe and boost your confidence as you move through your work weeks.

Stegmann Men’s Original 108 Wool Clog
Also available in Women’s!

fall fashion essentials

Nothing says Fall Fashion more than a pair of wool clogs and Stemann has some of the coziest and most functional around. Stegmann’s Original 108 Wool Clog comes in both male and female versions. Their smooth, soft Merino wool felt wraps your foot in comfort, while their orthopedically shaped cork & latex sole provides impressive support and cushioning for your feet and back. This clog offers you a generous toe box. Stegmann recommends ordering your usual shoe size if you plan to wear socks or have a higher volume foot. They recommend sizing down 1/2 size for barefoot wear, or if you prefer a snug fit (as this clog will loosen over time).

Stegmann’s Original 108 Wool Clogs are designed for indoor and outdoor wear. This clog does not have a removable insole or insert – the upper is a single, seamless piece of wool. The 108 Wool Clog features a Merino wool blend upper, a shaped cork & latex support sole, structured arch and metatarsal support, and cushioning with medium-level firmness. As a product of Austria, you can expect quality second to none. The 108 Wool Clog comes in a variety of attractive shades to choose from. Retails for $145 at

ROMEO NYC Merino Wool Raglan Crew Neck Sweater

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Get in the sweater weather mood with the ROMEO NYC Knitwear Collection! ROMEO NYC offers timeless apparel of quality and comfort. Their sweaters are cleverly detailed yet practical enough for everyday wear, allowing you to run your day with style and ease. The ROMEO NYC Merino Wool Raglan Crew Neck Sweater is the classic raglan sweater updated with a stylish zig-zag knit and banded detailing for a polished, effortless look. This sweater features 100% sustainably sourced Merino Wool, standard fit, ribbed hems at the waist, cuffs, and neckline, as well as a stylish zig-zag pattern with contrasting color detail. In choosing this attractive ROMEO NYC sweater, you’ll enjoy the benefits of Merino Wool in that it’s temperature regulating, ultra-soft, UV sun protective, and easy to care for. This sweater comes in Mid Grey, Beige, and Red. Retails for $69.90 at

A Few Wood Men – The Chadwick


A Few Wood Men offers the perfect Fall Fashion Essential for hardworking entrepreneurs who are seeking warmth, style, and sophistication this season. A Few Wood Men is not just a brand; it’s a celebration of success, resilience, and individuality. Their exquisite wooden watches and bracelets are designed to not only elevate your fashion game but also embody the spirit of hard work and success. A Few Wood Men’s The Chadwick is the epitome of a man who exudes confidence and leadership. He is everything the modern-day gentleman demands in a good wristwatch, which goes beyond keeping time. This 3-atmosphere water-resistant automatic-self-wind watch is powered by the motions of the man that honors it. This innovative timepiece is durable and lightweight, with a Hardlex dial window and a hidden push button clasp.

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The Chadwick mechanical wristwatch for men is where panache meets technology and it is designed to last a lifetime. It is inspired by their Black Panther forever, Chadwick Boseman, making it the perfect watch for entrepreneurs who exude strength, confidence, and vulnerability. Being that the watch you wear offers your meaning of success, you want a watch that exudes style, taste, and elegance. The Chadwick will add elegance to your business attire and it will also ‘dress up’ your more casual wear. Its warm tones also complement the color combinations of a fall wardrobe. Its specifications are: Bandwidth 22mm, Band length 220mm, Dial diameter 45mm. Retails for $390 at

Cozy Earth Men’s Ultra-Soft Bamboo Jogger Pant

Chadwick Boseman

A comfortable, quality jogger pant is a Fall Fashion Essential must-have. The irresistibly soft Cozy Earth’s Men’s Bamboo Jogger have all the coziness of pajamas woven into a stylish silhouette you can wear just about anywhere. Made with viscose from bamboo and a zippered back pocket, these men’s bamboo sweatpants will be your softest staple wardrobe whether you’re staying in or stepping out of your home office.

This jogger is made with 62% Premium Viscose from Bamboo, 28% Acrylic, 10% Spandex. Its fabric is breathable and moisture-wicking making you feel degrees cooler than cotton. Cozy Earth’s Men’s Bamboo Joggers come in ‘Tall’ if that is your better fit as well as in a variety of attractive colors. You’ll love that Cozy Earth stands behind their quality in that their loungewear, towels, and clothing are all warranted against pilling, abnormal rips and tears, and workmanship defects. Retails for $165 at

DUER No Sweat Moleskin Shirt


DUER’s apparel is designed for “doers” to move comfortably from bike lane to boardroom to an evening out all in one outfit. The DUER No Sweat Moleskin Shirt is a perfect Fall shirt, designed with a dropped shoulder and room through the waist for the option to layer. Integration of stretch offers comfort and ease of movement. This attractive shirt features a sleep front pocket with an eyeglasses compartment, high-stretch fabric, all-natural corozo buttons made from a nut, super soft fabric, and TENCEL™ Lyocell to naturally inhibit bacterial growth. The fabric consists of 68% Cotton, 30% TENCEL™ Lyocell, and 2% LYCRA® Spandex. To find the perfect match, this handsome shirt comes in six shades. Retails for $129 at

Milwaukee Boot Company Kane Casual Chukka Boot

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A chukka boot is a perfect Fall Fashion Essential for your wardrobe, as they can be dressed up or down. Comfort is no concern when it comes to Milwaukee Boot Company’s Kane Casual Chukka Boot. This deconstructed leather chukka is proof that cool and comfortable can work together. You can pair it with your favorite crew socks or go without as their unlined construction gives the Kane chukka added breathability. This chukka boot is available in dark cognac or chocolate suede leather.

The Kane Casual Chukka Boot features a premium suede upper, a premium leather padded Ortholite® footbed for maximum comfort, a Goodyear Welted EVA outsole for lightweight longevity (can be replaced over time), and shock absorption. Its deconstructed leather design allows for easy packing as you travel for work or leisure. You’ll love how versatile these chukka boots are which is important when going from your home office to business meetings. On sale now for $199 at

Steggy’s Henleys The Perfect Henly


A cozy Henley is a Fall staple essential for every entrepreneur’s wardrobe. After spending 1M+ minutes comparing various brands, working with experts, and undergoing extensive R&D, Steggy’s Henleys has crafted the perfect Henley that they guarantee will be the main character of your wardrobe. Steggy’s Henley shirts are versatile and durable all while prioritizing extreme comfort. They feature a Henley collar, custom tortoise shell buttons, a curved hem, and elastic-enhanced cuffs. Their proprietary materials are cotton, lyocell, and spandex. You can choose from shades Heather Grey, Charcoal, and Black. Retails for $75 at

Western Rise Evolution Pant 2.0

Green Heather

For all your Fall business travels, a good pair of jeans that help get you there is a must-have. The Western Rise Evolution Pant 2.0 are the perfect men’s casual travel pants made for travel, outdoors and everyday activities. From international flights to nights out and everything in between, these durable-meets-lightweight, 4-way stretch travel pants will keep you cool and comfortable. Western Rise designed the Evolution Pant to look great and feel casual so you can travel in luxury.

Evolution Pant 2.0’s proprietary air-texturized nylon twill feels like cotton while retaining the durability of nylon. Combined with the 4-way stretch of spandex and a stain-resistant, durable water repellent, these pants are ready for anything. The Evolution Pant can be worn multiple days in a row without washing and packs smaller than a t-shirt (lightweight versatility). This is a pair of men’s casual travel pants that dresses up enough to get through any meeting, yet is rugged enough for any outdoor activity. The Evolution Pant comes in a variety of shades to meet your wardrobe needs. Retails for $128 at

Trendhim Accessories: Fawler Frisco Rust-Red Urban Tube Scarf and Black Merino Wool Chunky Knitted Rib Beanie

Hand feel

Trendhim designs quality men’s accessories that are fashionable and affordable. They currently have 13 brands in their portfolio, one of which is Fawler. Fawler’s Frisco Rust-Red Urban Tube Scarf is a cotton-blend tube scarf for men that keeps your neck warm and lets you face the older months without scratching. Crafted with skin-friendly materials, this scarf doesn’t require tying or styling. Simply slip it on and go. It features a Danish design. Retails for £45 at

Heather GreyEvery entrepreneur needs a go-to warm, good-quality beanie that keeps your head warm all season long and Fawler’s Black Merino Wool Chunky Knitted Rib Beanie is just that go-to Fall fashion essential. This soft knit beanie for men will keep your head warm all season. It is made to the highest standards with premium 100% merino wool to easily withstand the elements. This is Danish designed. Retails for $45 at

DANDY & SON OSLO Extreme Cutaway White Premium Weave Shirt French Cuff

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Dandy & Son is the home of the extreme cutaway collar. Founded in Norway, their brand draws inspiration from the functional, minimalistic and unique style of Scandinavian fashion. Dandy & Son dress shirts are crafted to the highest standards using premium fabrics, elevated to the next level with small hints of distinction and detailing. Their flagship design, the extreme cutaway, features bold and assertive exaggerated tapering that captures the eye.

Dandy & Son Extreme Cutaway White Premium Weave Shirt French Cuff is a luxurious white shirt featuring a high-quality, easy iron fabric that boasts a beautifully textured weave. With Mother of Pearl buttons and their signature Extreme Cutaway Collar, this shirt exudes sophistication and style. This shirt is offered in their tailored Dandyfit™ design with a modern silhouette or classic regular fit. Featuring French cuffs and 100% premium cotton with an 80/2*40 thread count, this shirt is as comfortable as it is stylish. You’ll love that it’s easy to care for – simply toss it in the washing machine! Retails for $109.00 at

Los Andes Shop Western Poncho Clint Eastwood Replica

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Los Andes Shop has an interesting story of how it came to be. It all began in 1988 because of a passion for travel. Starting with importing hand-knit sweaters from family and friends in Chile, Los Andes Shop soon would discover Otavalo’s (a town high in the Andes) famous colorful “Plaza de ponchos’. In developing friendships with several Otavalans, they soon began importing the beautiful alpaca and woolen items created in this town and neighboring Peguche. Many of the artisans who develop Los Andes Shop’s beautiful goods are women or moms whose sewing or knitting at home allows them to support their families.

Los Andes Shop’s Western Poncho Clint Eastwood Replica is fantastic for any Clint Eastwood fan looking for a bit of warmth and softness for one’s fall wardrobe. You’ll love how amazingly soft and supple this poncho is. Created by native artisans high in the Andes mountains, you’ll stay warm and look great wearing this Western-style poncho made in Los Andes. This poncho’s size is one size fits most and all you need to do is pull it on over your heard, add your denim, hat and boots and you’re ready to go. This poncho has an option to add a hood as well. Retails for $75 at

TOPO Designs Global Wool Sweater – Men’s


A good wool sweater is a fall fashion essential every entrepreneur needs in their closet. TOPO Design’s Global Wool Sweater – Men’s offers a double-knit mesh back, making this wool sweater as comfortable next to the skin as your favorite tee. It features a classic fit and styling which makes it easy to complement any outfit, for any occasion. This is a sweater that gives you the approachability you’re looking for in those more casual business meetings. You’ll love that it’s machine washable, durable and uniquely versatile. It contains 65% post-consumer recycled Italian wool and is available in a variety of nice shades to meet your wardrobe needs. Also available in women’s. Retails for $139 at

Surfside Supply Co. Rex Rib Knit Shirt – Green Heather

Los Andes

Surfside Supply Co. is a brand for those who love the beach and who embrace that lifestyle. With the cooler weather on its way, comfort is at the forefront of your wardrobe styling. Each piece they design is intended to evoke a sense of comfort and ease.

Surfside Supply Co.’s Rex Rib Knit Shirt – Green Heather lets you enjoy broken-in softness right off the bat, while still looking sharp for the office, lunch meetings, and dinners. This button-down features a finely ribbed high-quality cotton blend fabric (60 Cotton / 40% Polyester) that is breathable as well as warm. Its classic detailing upgrades such as its button-down collar, flap button pockets, sleek button cuffs and contrast stitching at the shirttail hem give you the polished relaxed look you are seeking. With a shirt this versatile, you’ll want more than one color to meet your fall wardrobe styling needs. Retails for $98 at

Proto101 Men’s French Terry Zip Hoodie and Jogger Set

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Proto101 strives to provide better alternatives to disposable, “fast” fashion by sourcing sustainable fabrics, making durable garments in timeless silhouettes, supporting an ethical supply chain, and amplifying minority voices. Proto101 offers better basics, made to be soft on you and the planet. The clothing is timeless, made with high-quality materials that will last, so you buy less over time.

Proto101’s Men’s French Terry Zip Hoodie and Jogger Set is a classic hoodie and jogger you’re looking for in your fall wardrobe, and it’s made better. The French Terry Zip Hoodie is made with sustainable materials like American-grown Supima cotton, TENCEL lyocell, and recycled plastic bottles. Designed to accommodate your busy lifestyle, Proto101’s hoodie features a side-seam hidden pocket to keep your keys, cards and phone conveniently stashed away and you looking great. The Proto101 Zip Hoodie and Jogger Set feels like a cloud without looking like gym clothes. This is something you can feel good in as you sneak away from your home office to get your work out in. Hoodie retails for $89 at Jogger Sweatpants retails for $79 at

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