How to Dress Confidently as a Man

Undoubtedly, confidence stems from within yourself. However, it doesn’t hurt to have your style be a vehicle to express who you are. Not only does your look impart a hint of your personality, but dressing authentically also makes you feel more self-assured.

Whether you are already attuned to your sartorial flair or curious to know how to make your fashion fantasies a reality, read on to discover our process for building a confidence-inducing wardrobe. 

Know Yourself

The most important step in learning to dress with confidence is to know your own style. Perhaps you have an established aesthetic, or maybe you are taking the leap to develop your signature look. If you have a clear sense of style, dressing true to who you are likely already brings you confidence. If not, then you are at the beginning of a very exciting journey. That journey starts with our next tip.

True style comes from knowing yourself.

Do Your Research

What style are you drawn to? Perhaps you enjoy watching classic movies and want to emulate an effortlessly cool James Dean vibe. Likewise, contemporary celebrities can be a source of inspiration as well. Maybe you want to emulate Henry Golding’s classic-yet-preppy tailored look, or your fashion goals are to mix colours, patterns and fabrics with the ease of Donald Glover’s truly distinct style. Testing the waters by modeling your outfits after your style icons will give you a sense of what looks work for you.  

Lastly, Instagram feeds like Adesso’s can be a fantastic place to start researching your style as we regularly post tips on trends and fashion advice.

Acquire the Basics

There are certain pieces that every man needs. Starting your adventure into elevating your style starts with:

  • Perfectly fitting jeans in a flattering wash
  • A pair of neutral chinos
  • A pair of joggers
  • A pair of dress pants
  • A variety of button-down shirts
  • At least one chambray shirt
  • At least one black turtleneck
  • At least one crewneck sweater
  • A selection of fitted t-shirts in neutral tones
  • A tailored suit
  • One bomber jacket
  • One pea coat
  • One sports jacket
  • A pair of stylish sneakers
  • A pair of dress shoes
  • A pair of Chelsea boots

The key to feeling confident in your clothing is fit. Even a minimalist wardrobe — although we are supporters of taking your style to the next level — looks effortlessly chic permitting your clothes properly fit you.

If you are unsure of how your clothing should fit, take the opportunity to speak with a stylist (many department stores and local boutiques have access to on-site stylists) or a tailor to know what sizes and fits you should be looking for.

Start with the basics to build your wardrobe.

Accessorize, Accessorize, Accessorize

Ah, the fun part. Accessorizing is how you elevate a great outfit to a look that communicates who you are — and when your outer appearance emulates who you are within, you will feel more confident. For example, novelty socks add a pop of personality to your day-to-day office suit. A tie and coordinated, not necessarily identically matching, pocket square brings a sense of sophistication to your evening wear. Stacked bracelets layered with a watch communicate exceptional taste when worn with a casual tee and jeans. A leather satchel not only is useful but renders your look to be utterly on-trend.

With accessories the options are endless, and we invite you to let us know your accessorizing questions either by vising us in-store or by messaging us directly on social media.   

Break the Rules

Like any well-practiced craft, there comes a time in each stylish man’s fashion journey where he can go beyond the basics and truly encompass his authentic look. Like how professional photographers know when not to use the rule-of-thirds or how chefs blend seemingly unrelated ingredients to create a masterpiece, so too will you know when to wear a velvet blazer or floral-patterned shirt — possibly paired together.

Dressing with confidence means knowing when to break or build-upon fashion rules.

There you have it, a step-by-step guide to cultivating confidence through developing your personal style. Keen to know how to likewise feel more self-assured through your personal care? Take a look at our recent blog post for additional insights.  

2 comments

This is genuinely helpful information – thanks so much for sharing.

I’ve spent many years as a married man shopping from chain stores in malls. Becoming single at any stage in life re-awakens a sense of needing to look and feel good about yourself. Knowing where to start can be hard, so coming across this article has been a great inspiration! I have a new bucket list for my presentation skills and it starts with acquiring the basics! Onward and upward!

Scott Boswell May 07, 2020

Thank you for this blog post. I spent years not knowing who I was and how I wanted to appear in society. Large changes in my life finally pushed me down the right path and my wife Monique help push me along when needed.
The hardest part for me was finding the right places to not only find the right style of clothing, but finding the more European, slim and tailored fit I wanted.
I’m well down this self style-identified path now and love what has come to market and especially retail locations that have catered to the style conscious man! Thank you Abdul for the great post and Adesso Man for all that you are!

Stephen Shaw March 29, 2020

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