Men's Fashion Trends in 2020

Men's Fashion Trends in 2020: Looks Every Man Can Wear

Since spending money on quality pieces that last forever is the standard approach most men take when it comes to their wardrobe, excitement about the latest fashion trends in menswear is generally only celebrated by a very small contingent. So, if you are not really into jumping on the cross-body bag trend and are quite happy to let your lady sport the high-waisted flared jeans look that dominated Men's Fashion Week, you aren't alone. However, avoiding floral sheer blouses doesn't mean you need to give up looking stylish, because not all fashion trends are created equal. Understanding the difference between flashy fads and forever classics is the key to looking good, feeling confident, and not staying stuck in the same old get up year after year.

To help you head in the right direction, Westport Big & Tall has selected the latest in the menswear movements for 2020 that are worth incorporating into your wardrobe. Classic and updated, casual and a bit more formal, these 10 wardrobe essentials are the basics every man needs in his closet this year.


Pockets will be a big part of this new fashion decade and it all began in 2019 when cargo pants had a huge comeback. 2020 will see this cargo comeback grow and they will be a massive style trend this year. For the last few years everyone stayed far, far away from the multi-pocketed pants and shorts, however the "New Cargo" are more modern and fall into the functional "utility" category that is on the top of the 2020 menswear trend.

Westport Black Stretch 5-Pocket Denim Jeans

Lighter Shades of Denim

The nod to 90s fashion began in 2019 and continues strong this year as menswear gets into the game, and what is more 90s than light wash denim. Dark and raw denim will always be a fashion classic, but as we enter the warmer months darker jeans become less practical. Including light shades of denim in your jean rotation this summer is the key is to keeping things casual, light, and fun. If you aren't sure what shoes to wear, go with a pair of white sneakers - they work better than a dark shoe and provide the modern look this trend deserves.

A Utility Vest

2020 will see a lot of "utility" type clothing (hello cargo) and the vest will be on the forefront of this trend. Layering over a t-shirt in warmer weather or under a jacket during the transitional months, the vest with pockets is no longer just for workwear or the local fishermen. The utility vest is a great way to add a contrast of functionality and modernity to your wardrobe.

Peter Millar Short Sleeve Summer Soft Pocket Tee Shirt

The White T-Shirt

It doesn't get any more classic or versatile than the white T-shirt. Originally only reserved as an undergarment, the white t-shirt went from a background character to the star of the show in the 1960s and symbolizes everything from rebellion to athleticism to high fashion. The white t-shirt has taken its place as a staple in men's fashion and is an easy item that can be worn with anything. Whether you wear it underneath a casual suit jacket for an evening out or with a pair of shorts during a family outing, a crisp white t-shirt is a must have for every man.

Peter Millar Hyperlight Suede Bit Loafer

Loafers That Go With Everything

Loafers are classic and iconic, and are making a resurgence as the go-to shoe for men in 2020 according to Westport Big & Tall. The loafer is the perfect in-between shoe, fitting right in the middle of the sneaker and the more formal leather shoe. It is hassle-free footwear and a must add to your wardrobe this year. Loafers work well with everything from shorts to jeans to chinos and suits and will automatically elevate whatever you are wearing.

Polo Ralph Lauren crewneck sweater

A Simple Crew Neck Sweater

The crew neck sweater is another classic that will make any outfit you add it to just look that much better. A great option to replace the white tee when you need to bring a little more sophistication to the occasion, or with a pair of shorts if you are feeling into the preppy resurgence of 2020. Level up the complexity by layering a crew neck sweater over a dress shirt when you are looking for an alternative to the business suit. A crewneck sweater can be one of the most versatile pieces in your closet and is perfect for creating a timeless casual look.

Polo Ralph Lauren hoodie

An Everyday Hoodie, For Every Day

Over the past few years menswear has been getting more casual and the ever surging love for everything hoodie isn't stopping any time soon. Offering warmth and style, hoodies are the perfect addition to every man's closet. One of the best characteristics of today's hoodies is the variety of style options available, so no matter what the occasion there is sure to be a hoodie that will allow you to fit right in, comfortably.

Polo Ralph Lauren Double-Knit Jogger Pants

A Pair (Or Two) of Great Joggers

Like the hoodie, joggers are continuing to gain popularity as a wardrobe staple that can easily go from the couch to the cocktail lounge. No longer relegated to the gym, the jogger's versatility allows wearers to look relaxed and stylish at the same time - depending upon their mood and the occasion. If you are looking for a comfortable basic that you can wear to the gym, out with friends, or for a weekend of binge watching Netflix, nothing is better than a great pair of joggers.

Polo Ralph Lauren Black Wash Stretch 5-Pocket Jeans

Black jeans.

As a necessary staple in your wardrobe for 2020, black jeans are a neutral base jeans that will go with everything. Black jeans always look stylish and whether they are paired with a crew neck sweater, dress shirt, or a white t-shirt, they are the perfect pair of pants to fit in at any occasion.

The Polo Shirt

This year, menswear will see a lot of modern updates of traditional preppy fashion, and the polo shirt is near the top of the list. Today's polo trends include nods to the old school style as well as more updated versions that aren't just for playing tennis or cheering on your favorite lacrosse team. Today's versions move beyond the country club and with different prints, fabrics, and fits, the polo is being included in as a part of many different types of style vibes.

Remember, being on trend doesn't mean throwing your comfortable basics out the window. The essentials listed above are great pieces to add to any man's wardrobe and can easily enhance your look and fashion sense without sacrificing your personal style.