For men, the time between your teens and your 30s is riddled with constant change. This is why knowing how to dress for your 20s can be confusing. No worries. I’m here to help.
Your 20s are an exciting time. College is behind you, and the chapter of life when you learn to make real adult decisions has begun. This includes figuring out how to dress in your twenties.
It’s a transitional chapter in life, with one foot in the world of youth and the other planted in adulthood. You’re still doing a lot of the same things you did in college.
You’re interning, working an entry-level job, or perhaps in graduate school. You’re going to similar clubs and bars. House parties may not seem that different from the ones your frat throws.
But you are aware that eyes are on you in a different way. Every move you make at work may or may not lead to a promotion. You’re learning a bit more about wine pairings instead of just stocking your bar with budget vodka.
With all of this comes an equally transitional wardrobe.
How To Dress in Your 20s: The Importance of Gradual Changes
If you have the resources to hire a stylist to completely makeover your closet, definitely go for it.
However, there are two reasons why it’s easier to transition your wardrobe gradually. First, it’s easier on your budget (this is a time you should be saving and investing). Second, it allows you to take baby steps into your full adult wardrobe, which makes it less overwhelming.
Work Clothes Upgrades
Start by upgrading your work clothes. If you work in an office, get yourself a really good custom suit. If you can get two, go for it. Otherwise, just find another suit jacket.
Do this even if you don’t wear full suits to the office. I know that in some white-collar work environments these days, it isn’t even advisable to wear full suits (more on that later).
But suit separates go a long way in almost every dress code. They allow you to easily create far more outfits than you can even imagine.
A suit with a T-shirt is perfect for nights out, dates, and networking events.
You can easily level up jeans and a t-shirt with a suit jacket on a night out with the guys.
If you can get a made-to-measure (MTM) suit and a MTM sport jacket, that’s ideal. Otherwise, you’d be surprised how much a half-off Ralph Lauren suit from a department store levels up with a little tailoring. Or maybe you buy one budget suit to be tailored and one bespoke jacket.
If you don’t work in a formal, or formal adjacent, work environment, upgrade your clothes using fit.
Perhaps you wear workwear on a daily basis. See if you can incorporate blazers and structured outwear into your personal style.
Even if you don’t wear a suit often, simulating a suit-like silhouette with casual clothes creates a grown-up look.
The Importance of Being Respectful
Perhaps your boss wears a simple navy suit and tie to work. In that case, don’t stroll in with a full ‘80s power suit, vest, yellow gold Rolex, and a diamond-encrusted tie-clip with matching cufflinks.
The old adage to dress for the job you want, not that job you have, is true. However, overdoing it might add, “and I’m coming for your job, boss”, to that adage.
On the other end of the spectrum, you might work at a casual tech company, and your boss wears a T-shirt and jeans. This is a completely different work culture. Here, you should think of it this way: He’s earned that right.
You should still be casual and dress within the company culture.
But to be respectful here, find ways to make your casual outfits more professional. Some good garment options include chinos, loafers, minimalist
Dressing in Your 20s and Finding Your Style
Some of you may have an innate sense of personal style. My advice to you is to see how you can start to make it more grown-up.
As an example, growing up, my school uniforms included a lot of primary colors. That being the case, I always felt comfortable in primaries. I still do, and I’m 35. However, outside of a Fourth of July party, wearing red, white, and blue can often scream little kid.
To make this palette I love more grown-up, I’d go for navy instead of true blue Similarly, crimson or even maroon is better than red, and beige or ecru instead of true white.
That being the case, it’s possible that you already have a personal style and don’t even know it. What clothes have you always been the most comfortable in that make you feel like yourself?
A T-shirt and jeans? Perfect. Keep going with that, but make sure you find the right fit that flatters your body type. Incorporate grown-up accessories like structured outerwear and a good wristwatch.
Perhaps you spent all of your college career in sweats. Well, try a fitted cashmere hoodie with fitted, cinched joggers and low-profile leather
Are you completely lost and have literally zero clue what style best represents you? Easy. Just go for a smart casual look anytime there’s no dress code.
Incorporating Trends
The 20s is a cool time in that people won’t bat an eye at your style mistakes. You owe it to yourself to take advantage of this.
And here’s the thing: Even a 40-year-old man can get away with trends as long as he’s intentional and dresses for his body type.
Do you like the look of skinny jeans (a past trend)? Fine. But if you’re strong in the leg area, an actual skinny fit will look downright shrunken on you. Go for a slim fit with zero to no break and a hem that doesn’t ride up as you walk.
Do you love bright colors? There’s nothing wrong with that. Just make sure to temper them with menswear neutrals like beige, tan, olive, and navy.
You’re at an age when trends seem perfectly appropriate. As you grow up, you’ll have to be more strategic about them.
The way to do this is by incorporating an aesthetic or fit that looks enough like the trend but isn’t exactly.
A hemmed, relaxed-fit pair of trousers will register as oversized, but you’ll maintain the clean lines of a classic look.
Want to participate in the pearl-necklace trend? A thin strand of mini stainless steel beads, with a few small pearls mixed in, is a good choice. It will register as a men’s pearl necklace without looking too gender-bendy.
By doing strategic adjacent looks to the trend in question, you can look like you’re participating without looking faddish.
You aren’t too old for a cool graphic tee yet. And, no one is too old for a vintage tee partnered with well-built workwear-inspired outerwear. A vintage band tee with a waxed jacket or a retro graphic shirt with an unstructured blazer are good examples.
What About Formals? Do I Need a Tuxedo?
At this point in your life, you may have attended a few black-tie formals. Perhaps you’ve attended charity galas with your parents, or maybe your college had some formal ceremonies.
But, probably not.
If you have attended black tie formals, and you do own a tuxedo, I just recommend making sure it’s up to snuff. Unless your parents are sartorial experts who regulated your formalwear, it’s likely your tux is missing important details.
Tuxedo shirts are different from white dress shirts. Tuxedo pants tend to have silk detailing, and so on.
Find any gaps to fill and fill them. Perhaps you just need to get it retailored as you slowly enter into your grown-up physique.
If you’ve never owned a tuxedo before, consider how often you go to formal events and what your budget is. Only attend formal events only once a year or less and are tight on finances? In that case, you might be better off renting instead of investing.
Or, you can always borrow your dad’s. As you move from your early 20s to your late 20s, you’ll likely start to attend more formal events.
Maybe not, but formal events are definitely more common in the adult world than in the 20-something world, where all things are held constant.
Ultimately, the importance of a tuxedo in your life depends on your lifestyle.
Outfit Examples
Let’s take a look at some cool combinations for all personal styles and every dress code.
A More Grown-up Version of a Youthful Combo
This combo is a quintessential transitional outfit in that, theoretically, it’s something you can also wear as a teen.
However, for your 20s, you want a slim-to-regular fit on the jeans and clean white
Classy with a Hint of Trendiness
This combination is a perfect example of how to incorporate trends in a classy, non-faddish way.
The suit flaunts clean lines and a perfect fit on the shoulders. Meanwhile, the trousers have clean lines. Also, they’re hemmed not to bunch, so it still looks grown-up.
Meanwhile, the traditionally masculine vibe of the whole outfit neutralizes the effect of the pearls, a huge trend among Gen Z men right now.
Textures are Important
The power of texture can make a youthful outfit more rugged and adult-looking.
This gent mixes cues from Ivy style and Americana, from the denim (or, more likely, chambray) to the braided belt. Your 20s aren’t the time to completely let go of youthful aesthetics.
The reason this outfit works, despite the veritable feast of textures, is because he anchors it all in three solid colors. If you go maximalist with textures, then go minimalist with color.
Even When You’re Casual, Clean Up Those Lines
Here’s another trend-forward outfit that shows the positive effects of clean lines and a neat silhouette.
Forget your oversized, athletic hoodies (or reserve them for runs on cold days) and go for a well-fitted cashmere one.
You’d be surprised at the range of pant styles that’ll pair well with it. In this case, he goes for a handsome pair of linen or lightly woven wool trousers in beige. It’s a stylish high-low combo with tons of cool factor.
Suit Separates
And finally, here’s an excellent example of the power of suit separates and good fit.
Despite being a broken suit, the tailoring makes this outfit look as formal as a traditional monochrome suit. The vest helps as well.
Conclusion: Have Fun, Be Appropriate
As long as you anchor most of your look in well-fitted basics and neutral palettes, you have room to experiment a bit. That’s the biggest takeaway I hope to impart when it comes to how to dress in your 20s.
We’re all bound to dress codes, whether spoken or unspoken, in our day-to-day lives. So it’s important to always look put-together. (Even when you’re having fun navigating your style identity.)
Are you in your 20s and just learning how to dress for the real world? Perhaps you’re older and have some advice you want to share. Let me know in the comments!
