How Men Should Dress in their Twenties

Posted by Rishi Chullani on

Anna Levinson

In this detailed men’s style guide, we cover how men should dress in their twenties – from smart casual to business casual and formal wear – showing you how to look your best in the basics.

As a man ages into his twenties, the exploration of his personal style becomes more important. While this transitional period can be challenging enough, figuring out how to dress is imperative to building a strong impression and can begin to characterize your image into your thirties and beyond.

Learning the basics of smart casual, business casual, and formal wear will set you apart from your peers and give you the tools to better reflect how you want to be perceived in all aspects of life. This detailed guide will ensure your sartorial success, whether you’re a budding professional, aspiring creative, or anything in between.

 Dressing In Your Twenties For Men

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The Capsule Wardrobe

Before diving into the specifics of clothing, we need an idea of what to work towards. Building a capsule wardrobe means acquiring quality pieces that complement each other. You should feel and look good in these pieces, rather than submitting to the ever-changing nature of trends (which will only leave your wardrobe feeling disjointed).

While a trendy piece here and there will help refresh your wardrobe, learning to dress for your own lifestyle is better than emulating other people. Capsule pieces will seamlessly work together to create versatile and cohesive outfits.

Fit and Quality

The most important factor for looking sharp is the fit of your clothes. From jackets to joggers, how an item works with your body is crucial for a more polished look.

Shop staff should be able to give you pointers on the best size and cut for you. For those in the prime fitness of their lives (which is often the case in your twenties), slim-fitting pieces will likely look the most attractive. Having shirtwaists taken in, sleeves and cuffs modified to your arms, and trousers fitted snugly will create an appealing silhouette suited to your youth.

How To Dress In Your Twenties For Men

Well fitted clothing is the backbone of any developed wardrobe! Courtesy of

Springing for higher quality fabrics like silk and wool will also pull a lot of weight in the sophistication department, and these pieces will last longer as staples in your closet.

Knowing When To Splurge

Investing in quality pieces is great in theory, but the budget you have in your twenties may be a little tight. To save some money, buy suits off the rack and bring them to a local tailor for adjustments. Basics like sweats and t-shirts tend to be more disposable, which is fine for this time in your life. There’s no need to fill your wardrobe with designer white tees that will wear out after a few hot washes, so don’t worry too much about splurging here.

Now is a good time to find a professional tailor in your city that you can continue to use for adjustments in the future. Buy an easy-to-style, versatile suit like a two-button, single-breasted business suit in navy or charcoal and have it tailored to cut costs without sacrificing finesse. There will always be time to upgrade as you further develop your tastes.

How To Dress In Your Twenties For Men

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The Essentials

Assembling a stylish wardrobe doesn’t take rocket science, nor does it have to break the bank. Here are a few pieces that will form the skeleton of your closet and that can be diversified as your personal taste evolves in the future:


As the eye is naturally drawn to the torso, assembling a small but wide-ranging collection of shirts is central to your style. Picking options that can be easily dressed up or down will be the most cost effective.

  • Basic t-shirts – Having a small variety of these will come in handy for a casual outfit or for layering. You don’t have to throw out your college shirts just yet, but start opting for more simple, clean options in neutral colors.

How To Dress In Your Twenties For Men

A well fitted v-neck or crew t-shirt should be a staple in every discerning gentleman’s wardrobe in their twenties.

  • Light collared dress shirts – When you want a slightly more sophisticated edge to a casual look, light collared dress shirts are your best bet. These are another building block of a stylish capsule wardrobe with high versatility. Once you have these, you can start looking for other colors and patterns that match your personality.

How To Dress In Your Twenties For Men

A well fitted, light colored dress shirt can go a long way towards helping you refine your look & sense of elegance in your twenties! Courtesy of

  • Classic white shirts – No matter what field you’re in, you can’t go wrong with a fitted white shirt. Keep a high-quality, stiff-collared option for more formal occasions like job interviews and weddings, and then mix in some button-down Oxfords for work or other more (smart) casual outings.

How To Dress In Your Twenties For Men 

There are few situations where a dress shirt cannot elevate your ensemble!


  • Dark jeans – as a man learning how to dress in your twenties, jeans might be the most popular option for pants in your closet. Make sure to have a fitted pair of dark wash jeans in your variety. Dark wash denim is regarded as more formal than light wash, making dark jeans a flexible option that can be dressed up with a collared shirt or blazer. Black and indigo jeans also pair well with any kind of shoe, making them a stylish choice for any evening plans.

 How To Dress In Your Twenties Men

Dark Denim always provides for a great look. Courtesy of

  • Chinos – Chinos are usually lightweight, cotton-blended pants that come in a wide array of colors. They’re the prime example of business casual, and look great with your basic dress shirts for a smart look perfect for the office or dressed down with sneakers for the weekend.

How To Dress In Your Twenties Men

Chinos are a great addition to your wardrobe – regardless of decade! Courtesy of

  • Trousers – Trousers are a must for making that leap from casual to formal. They still boast major versatility, and look great with t-shirts, sweaters, and dress shirts alike. Grab some in your basic neutrals and earth tones to start.

 How To Dress In Your Twenties Men

Well fitted trousers are imperative in any aspiring dapper gentleman’s wardrobe. Courtesy of

  • Slim tapered joggers – Well-fitting joggers are the sweatpant’s more sophisticated cousin: they make a casual outfit look a bit sharper on the days where you’re not feeling dressy.

 How To Dress In Your Twenties Men

Athleisure sweat pants / joggers are the perfect way to leave your house feeling both super comfortable and stylistic!


  • A Navy blazer – Blazers are a great item for dressing up your wardrobe and are vital in this transition to a sharper look. Blazers and sports jackets look great in earth tones and deep hues, especially if there is texture either in the weave or the thread itself. Navy is a classic color and will match all your basics, making styling them a breeze. For additional style tips on navy blazers, check out our blog post on How to Style a Navy Blazer.

How To Dress In Your Twenties Men

A navy blazer will add instant gravitas any time you are looking to elevate your style game! Courtesy of


If there’s one thing to note about buying a suit – especially your first one – it’s to steer clear of poly-blend, ill-fitting, and poorly constructed ensembles. Material matters as much as construction and fit, so opt for strong and lasting fibers like cotton, silk, and wool. While bespoke suits don’t have to take priority just yet, there are other avenues to achieve a similarly elegant look.

  • Well-tailored suit – if done right, one good suit can cover a variety of your social needs. From work to weddings, a plain navy suit in a wool-cotton mix with half-lining is the most versatile. The color and structure is light enough to wear in the summer, or can be layered with a stylish overcoat for the colder months.

How To Dress In Your Twenties Men

A well tailored suit makes all the difference, and is an article of clothing every young gentleman in their twenties should aspire to have – even if it’s not bespoke. Courtesy of


Everyone has that beat up pair of shoes you’ve had forever, but now is the time to start spending wisely to elevate your footwear. There are only a few basics you need, but make sure they’re durable and look good with the clothes you have.

  • Sneakers – A good pair of sneakers is essential to a smart casual outfit. Start off with a comfortable white pair with clean lines that can be worn year round.

How To Dress In Your Twenties Men

Adding a pair of white sneakers to your wardrobe will instantly allow you to inject your ensembles with much needed stylistic pop! Courtesy of

  • Leather dress shoes – Oxford and Derby shoes are great options for more formal occasions, and are staples worth investing in. You only need two pairs for now, one black and one brown to match with your other accessories.

How To Dress In Your Twenties Men 

An exquisite pair of oxford brogues adds instant panache and credibility. Courtesy of

  • Sandals – For the warmer months, a sleek pair of sandals come in handy. Spring for higher quality to avoid a cycle of constant replacement.


An eye-catching accessory can accentuate an outfit and send a strong message about your personality and confidence. Often, they are the difference between good and great style.

  • Belts – You should have at least two belts, brown and black to match your dress shoes.

How To Dress In Your Twenties For Men

Brown Belt with Brown Shoes. Always imperative that you match the color of your belt to your shoes. Courtesy of

  • Socks – A man should have at least seven pairs of everyday socks, as well as athletic socks, dress socks, no-show socks and ankle socks. Keep these well stocked so you don’t run out on laundry day. You can also showcase your style with different colors and patterns.

 How To Dress In Your Twenties For Men

Colorful Socks add flair to the otherwise conventional. Courtesy of

  • Neckties – For more formal occasions, you’ll need a solid array of ties. Grab a couple in navy and other dark, solid colors. Also spring for some sort of small graphic print and a color that compliments your skin tone and the suits in your arsenal. Once you have a few reliable options, you can explore and take some style risks here.

How To Dress In Your Twenties Men

While Navy & Grey Ties are often considered staples, a more colorful tie can really bring your outfit to life! Featuring The Dark Knot’s Meredith Foulard Turquoise / Teal Silk Tie.

Silk Ties | Ties | Neckties | Shop Ties | Buy Ties

  • Knit Ties – For clarification purposes, we’ll add another category here. These ties are generally best worn in less formal capacities, and are therefore an ideal complement to smart casual dress attire. Knitted ties are characterized by a knitted (not woven) weave, and straight, square ends that lend to a more casual look. The knitted weave creates textural depth that adds both a level of casualness and textural variation to your attire, providing layered aesthetic appeal! In other words – whether you’re on an evening out or date night – knitted ties can definitely do the trick.

How To Dress In Your Twenties For Men

A Knitted Tie offers textural variation and depth, elevating your style game. Featuring The Dark Knot’s Livingston Navy Silk Knit Tie.

Knit Ties | Silk Knit Ties | Knitted Ties

  • Watches – like a navy suit or Oxford shoe, a good watch is something that will never go out of style. While not strictly a necessity, you can start off with a basic steel variety and work your way up to something more luxurious, or splurge right out of the gate on something that will last a lifetime.

How To Dress In Your Twenties For Men

Minimalist Watches provide a refined look without breaking the bank. Courtesy of


You only need a few durable options for your outerwear and top layers – stick to browns, blacks, blues, and other modest colors that match the bulk of your wardrobe.

  • Sweaters – Good, sturdy wool in earth tones and neutrals is a timeless option and will provide a classic sophistication, especially when paired with trousers. Dark-colored cotton sweaters are also great to have around for the colder months. Deep hues like burgundy and forest green are good options for colors.

How To Dress In Your Twenties Men

  • Jackets – Have a couple casual jackets like leather or a bomber jacket to add an extra stylish layer to your smart casual outfits.

How Men Should Dress In Their Twenties

A bomber jacket proves to be versatile and almost always does the trick! Courtesy of

  • Coat – One good, structured coat that will carry you through any sort of occasion is a must.

Taking Style Risks

While there is certainly merit to the simplicity of the classics, bold style choices are easier to pull off as a man in your twenties and are paramount to determining what works for you as you learn how to dress as a young gentleman. Taking more risks now will help narrow down what you’ll wear in the future.

There are some “rules” in fashion, and they’re good to follow, most of the time. However, now is the time when you can get away with standing out from the crowd and dressing outside your comfort zone. Learn the rules before breaking them, but feel free to be an individual. Experimenting with patterns and colors in small places – your tie, socks, and other accessories for example – is a good place to start. 

Incorporating color and texture

A little goes a long way when it comes to bright colors on men. You usually want two bright colors at most, with everything else in the outfit either more neutral or complementing one of the bright colors. Neckties and pocket squares are designed to be a splash of color, and are an easy way to take a little risk. Grab some trousers in gray and muted colors to start, and branch out with other earth or jewel tones.

Pocket Squares | Silk Pocket Squares | Linen Pocket Squares | Buy Pocket Squares | Shop Pocket Squares

Some shots of color in a patterned blazer also look nice, like a pink thread running through an otherwise subdued plaid. A contrasting belt works best for a slimmer build, and t-shirts can also add a small pop of color underneath other layers. Always pay attention to which colors work best with your skin and hair.

You can also liven up a restrained color palette with lots of texture and layering. After gathering some solid basics, you can sprinkle in vintage or more eclectic pieces to round out your style and better hone your look. 

How Men Should Dress In Their Twenties

Men's Stackable Beaded Bracelets are a great way to introduce texture and minimal fashion risk into your ensembles. Featuring The Dark Knot's Santa Cruz Grey Agate / Black Beaded Bracelets.

Men's Bracelets | Leather Bracelets | Beaded Bracelets | Shop Bracelets | Buy Bracelets

Looking fresh and sophisticated at this age seems more daunting than it is – follow this style guide and opt for simple over all, and you’re sure to look sharper than most of your peers. Polishing your shoes, ironing your shirts, and trimming your nails only costs time, and won’t eat away at your budget. Pay attention to the details and you’ll have a look to build from in no time.

And that's a wrap for this one! We hope that you have found this article both informative and enjoyable to read!

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