Fall/Winter 2021 Menswear Trends to Watch


It’s a common misconception that adhering to trends faithfully equates to being well-dressed. This is not the case, in our opinion. Maintaining your sartorial self-respect requires the capacity to correctly discriminate between transitory fads and future classics. It’s a recipe for lousy style to mindlessly follow every seasonal fad. Not to mention a fast track to bankruptcy. To help you get started, we’ve compiled a list of menswear trends worth incorporating into your wardrobe this year. 

Oversized Outerwear

Tailoring on oversized outerwear isn’t the only thing loosening up in 2021. Slouchy overcoats, long parkas, and boxy puffer jackets will all be trendy as we go towards winter. Oversized belted overcoats with embroidered patches, in particular, are deserving of special consideration.


Oversized outerwear gives you a lot of leeway with your underwear, allowing you to play around with textures and tones to create a lot of depth. In our opinion, this makes it a winner. This trend has a lot to recommend because it emphasizes one of the best aspects of winter menswear: the ability to layer. 


Fleece’s comeback is part of a broader trend in menswear toward outdoor-inspired clothes. This is a trend that works best when used in little amounts. Thick-pile vintage fleeces have been popular as standalone outerwear for several seasons, and designers are continuing to incorporate the fabric into their autumn/winter collections. Limit yourself to one fleece garment per outfit to avoid going full sheep, and mix and match it with other textured fabrics to provide more tactile depth to your cold-weather combinations.


Leather will be a trend year after year because of its fantastic appearance, toughness, and timeless appeal. It will not be inexpensive, but it will last a lifetime. Why not go for a model with a belted waist if you truly want to be on-trend? This coming winter is the perfect moment to add one to your collection if you haven’t already. A high-quality bomber jacket made of the material is likely to be one of the best stylish investments you’ll ever make. 

Textured Tailoring

When the winter weather arrives, ditch the smooth fabrics and watch your tailored styles take flight. Tweed, wool, twill, embroidery digitizing designs, and corduroy are just a few of the materials that may help you up to your sartorial game by adding character and establishing focal points to any outfit. Keep in mind that it will never look as sharp as classic tailoring, so save it for casual occasions like dates, parties, and weddings.

Technical Jackets

One of the overriding trends of the last several seasons has been the rise of technical outerwear in the fashion world, and it will continue well into the new year. Cropped, zip-up silhouettes are taking center stage this season – perfect for a quick trip to the shops or as a middle layer beneath your winter coat for added weight and protection from the weather.


Relaxed Legs

If you embrace a looser leg, though, you could be surprised at how much you enjoy it. Slim leggings are no longer available, and slim-fits are becoming scarce. We’re seeing a return to the relaxed-fit pants of the 1980s and 1990s in their place. Not just in terms of elegance, but also in terms of comfort. For the better part of a decade, many of us have been squeezing ourselves into tight-fitting jeans, and old habits die hard.

Chelsea Boots

The Chelsea boot has long been regarded as one of the most stylish, sleek, and low-profile boot styles available. The Chelsea boot with a commando sole. Thick, robust soles have become increasingly popular in men’s footwear, but nowhere are they more appropriate than here. Not to mention that the extra chunkiness expands your clothing possibilities, letting you experiment with looser fits and heavy layering. While this is OK in warm weather, once we’re hit with ice and severe rain, they’re no longer useful. Finally, this timeless silhouette is completely prepared to face the elements. 


Pinstripes were seen everywhere at the menswear shows, whether on large suits or wide-leg pants. A single-breasted jacket is a classic choice, but why not go full 1980s stockbroker with a double-breasted jacket with peak lapels? If business casual is too casual for you, invest in a high-quality pinstriped suit. It’s a welcome return for one of the tailoring’s best patterns. That’s correct, the world of tailoring has come full circle. Checks are constantly in style in some way, shape, or form.


There are a plethora of methods to incorporate these patterns into your daily wardrobe, but one of the most straightforward is through the use of an overshirt or flannel shirt.

Pockets galore

It doesn’t feel like it was that long ago that cargo pants were the pinnacle of uncool. A pair of jeans with additional pockets became less fashionable. This year, though, nothing could be further from the truth. Look for multi-pocketed outerwear from some of the industry’s biggest names as well. Pockets have returned, and this time they’re staying put.



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