From Boardroom to Bar: Transitional Outfits for the Modern Man

From Boardroom to Bar: Transitional Outfits for the Modern Man

I have read uncountable men's fashion material, done thorough research on related topics, and written thousands of men's fashion articles. I can confidently say that style and versatility in your dressing rank very high in the most critical things to consider as a modern fashionable gentleman.

Being in an ensemble that will allow you to effortlessly move from the desk to drinks or a dinner party while still maintaining a great sense of fashion is incredibly helpful. This will give you confidence as you will be dressed up perfectly for the distinct parts of your day without compromising on style or comfort. Also, it saves you time as you won't have to go back home and make major changes to your outfit.

Here, we'll explore styling tips for versatile outfits that embody sophistication and ease to ensure you're on point, whether closing deals or catching up with friends over drinks.

Styling Tips for Versatile Outfits That Can Be Worn for Both Work and Leisure

When it comes to versatile outfits, one thing underscores everything else: look sharp! Let's look at some fundamental principles and styling tips that will ensure that you look dapper in and out of the office in the same outfit.

Smart Casual Dress Code Is Versatile By Definition

In its definition, the term smart casual is a combination of the smart and dressier (formal) and the casual (sometimes flashy) forms of dressing. This means that the resulting outfit has aspects of dress codes worn in both casual and formal settings, which is exactly what we're looking for! We can, therefore, say that smart casual is at the center of versatile dressing.

A good example of a smart casual and versatile outfit is a white turtleneck shirt paired up with a dark brown suit jacket and matching suit pants. To complete the look, go for white sneakers and accessorize accordingly. Something important to note here is that the casualness or formality of your versatile outfit will depend on the nature of the events you expect to attend.

 Some of the key details that will help your outfit be primed for both a boardroom and a bar are:

The Classic Blazer

A good blazer effortlessly adds a touch of smartness to any look. Even the "amateur dresser" can easily pull a statement-making outfit with a blazer. A blazer is your number one go-to piece if you want to easily switch from a formal setting to a social outing. To maintain a sense of formality, go for neutral colors like charcoal, gray, or dark brown.

If the formal event is a little bit more to the formal side, the blazer, a crisp button-up shirt paired with complementary chinos, and some brogues will do. When you are out to the informal event, lose the button-up dress shirt and have a congruent t-shirt instead

If it is a less formal event, you can match the blazer with a button-down shirt and a fitting pair of chinos. A pair of elegant loafers will always do you justice in smart casual dressing, especially for this outfit. When it's drinks time, you can still maintain this exact look or lose the blazer and roll up the sleeves of your shirt, and you will be good to go!

With the Right Blazer, You Are Limitless!

I must emphasize that with a blazer, you are limitless! It all depends on the extent of formality for the formal part of your day. You can't go wrong with a blazer if you maintain neutral or dark colors. Pairing a blazer with a plain t-shirt, dark denim trousers, and Chelsea boots, for example, would be fitting for some formal settings, and this exact look would fit perfectly for a casual dinner party.

Always consider your style and look for inspiration on platforms like Pinterest, and pulling off a sharp look will be easy peasy!

The Classic Suit with a Twist

A well-tailored suit is another versatile outfit that will do you good if you can play around with it in the right way. For this, go for colors like navy or charcoal, as they are more adaptable. Opt for a slim-fit silhouette for a modern look. Pair your suit of choice with a crisp dress shirt and a patterned tie for a professional touch.

When it's time to unwind in the bar with your friends, lose the tie, roll up the sleeves, and swap the dress shoes for a pair of stylish sneakers that complement your look (the sneakers can match the color of your shirt) to transform your outfit for a night out instantly.

The Polo Shirt

The polo shirt is another piece that you can hardly go wrong with. Today, it is acceptable in most offices that don't call for so much formality in terms of dressing. In fact, it is commonplace for many Wall Street companies. Worn with chinos or khakis and complementing boots, you can seamlessly walk from the office to an evening out with friends.

The Versatility of Jackets

Depending on your style, there’s always a jacket that will bring out the fashionable gentleman in you and even have your confidence soaring. There are different types of jackets, and out of these, there are some that can be worn for a smart casual look. The staple smart casual jacket that every modern-day gentleman with style must have is the bomber jacket. Others include the leather and varsity jackets.

These jackets, especially neutral color jackets, can be paired up with anything to pull off a smart casual look during chilled days. For an ensemble fit for the boardroom  and the bar, here is an idea to work with:

  • Layer a lightweight button-down shirt underneath the bomber jacket.
  • Opt for dark-wash denim jeans for a sleek and sophisticated appearance.
  • Finish off the ensemble with suede Chelsea boots or leather loafers for a touch of refinement.

Stepping Up: Top 5 Versatile Footwear Options for Men

From the versatile outfit suggestions given throughout this article, we can already tell some of the most common versatile footwear options that will exude a sharp and stunning look. Footwear plays a pivotal role in completing any outfit, and when it comes to versatility, having the right shoes can make all the difference. Here are our top 5 picks:

1.     Classic Leather Oxfords

Although leaning more towards the formal side, leather Oxfords exude sophistication and versatility. Perfect for formal occasions, pair them with tailored suits or dress trousers for a polished look. To transition seamlessly to smart casual settings, pair them with chinos or dark denim jeans and a blazer.


2.     Suede Loafer

Suede loafers offer a stylish alternative to traditional dress shoes. Ideal for both work and leisure, wear them with tailored trousers for the office or with chinos for a more relaxed vibe.

Their versatility extends to casual outings as well; pair them with jeans and a button-down shirt for a refined yet laid-back ensemble if you don't expect to be in an extremely formal setting.

3.     Chelsea Boots

Chelsea boots are among the must-have shoes for any modern-day gentleman. They are a versatile footwear option that adds a touch of sophistication to any outfit. Pairing them with tailored trousers, chinos, or perfectly fitting denim jeans and a polo shirt will give a polished look fit for both an office and a casual party.

Their sleek and timeless design makes them suitable for various occasions, from formal events to everyday wear.

4.     White Sneakers

A wardrobe staple for the modern man, white sneakers offer endless versatility and style. Whether you're dressing up or down, white sneakers add a touch of contemporary flair to any outfit. Pair with everything from suits to jeans and even shorts for a casual-cool aesthetic that never goes out of style.

5.     Leather Brogues

Leather brogues are another timeless footwear choice that exudes elegance and charm. Choose a sleek, modern design in black or dark brown leather for maximum versatility. Pair with dress trousers, chinos, or even jeans for a polished yet relaxed ensemble that works for any occasion.

These are just some of the top picks, but there are many options out there that can work out well for you.


Outfits that are transitional and fit different settings can be a game changer for you. If you get the core principles right, stepping out in an elegant style and a dapper outfit will be so effortless for you. You just need to understand your style, know the level of formality required, and then play around with the suggestions in this article to understand what works for you. 

Check out our collection of versatile pieces that will give you confidence and comfort as well as a simple yet superior sense of fashion. If you ever need any assistance, don’t hesitate to reach out.



Written by Emmanuel Isaac- Content Writer and Editor at HolloMen

Emmanuel is an experienced freelance writer specializing in fashion. Combining research skills and creative storytelling, he crafts engaging content that's both insightful and stylish. Known for his unique mix of analytical depth and creative flair. ( 

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