We’re breaking down the style must-haves for your twenties, thirties, forties, and fifties (and beyond). Below, the #SGapproved guys’ wardrobe essentials for your 20s…
Why it’s time to upgrade your style in your twenties
Your twenties are an exciting time. You’re setting out on your own, beginning your career, and finally experiencing life as an honest-to-god, adult.
If your college experience was anything like ours, you left school with a questionably useful diploma (shout out liberal arts degrees!) and a wardrobe comprised almost exclusively of sweatpants and free t-shirts.
Time to address that second part! The first part of being an adult is dressing like one, because only when you start dressing like one can you feel like one. Trust us. In this guide, then, we’ll break down the essential pieces to invest in as you begin your journey to adulthood.
In your twenties (and really, through your whole life), you ought to consider how your clothes reflect on you in the professional world or otherwise. It takes a lot of people far too long to figure out that dressing well helps you (1) project the confidence of someone who deserves the corner office and (2) lets others know you’re not just there for a spring internship.
While you might be used to rolling out of bed and into sweats every day, in your twenties it’s time to start incorporating “grown-up” clothes into your wardrobe. Here’s what you need:
Below, the guys’ wardrobe essentials for your 20s
Navy Blazer
If there’s one thing you’ll be doing quite a bit of in your twenties it’s interviewing. Whether it be for a job or for grad school, the interview is your chance to sell yourself and dressing the part is half of the battle. Having a classic navy wool blazer in your closet takes a lot of guesswork out of figuring out what to wear to an interview.
The most versatile blazer is also the most classic, boasting a notch lapel, with a 2-button front. Look for a soft shoulder, which gives you the ability to easily dress it down.
The body should fit close, but comfortable. Be sure the back of the jacket lays smooth – and that it covers your butt. A good blazer pairs well with virtually any shirt/tie combination, though a white oxford (more on that below) is always a good choice. With a pair of grey wool slacks and a pair of brown dress shoes, you’re sure to get hired on the spot.
…Well, maybe not, but you’ll certainly make a great first impression.
In addition to being perfect for job interviews, a navy blazer is also a solid option for dates. There’s nothing a woman likes more than showing up for a first date and noticing the guy has clearly put effort into how he looks.
And a navy blazer with a crisp shirt, well fitting jeans, and clean lace up boots are pretty perfect for a night out on the town, no matter what your plans are.
//SHOP OUR PICKS//
>> How to wear a t-shirt and a blazer
White Oxford Cloth Shirt
When you’re first starting to build a wardrobe, look for pieces that can be dressed up or down. They’ll keep your closet from getting too unruly and help you save some money. A good oxford cloth button down shirt (OCBD) goes with literally everything.
Yes, literally.
An OCBD with chinos or jeans is a classic look that every guy looks great – and feels even better – wearing. Toss a sweater or sweatshirt over top for a dressed down look in cooler temps or a under a blazer to dress the look up.
Oxford cloth is an extremely durable and versatile material. In addition to being able to stand up to everyday wear and tear, it looks just as great with a blazer and slacks as it does with jeans. You can even class up your relaxed Saturday brunch look by pairing one with a pair of slim sweatpants.
Aside from fit, pay close attention to the collar. Look for OCBD’s with a button down collar tall enough to accommodate a tie when needed. Again, the idea is to get the most versatility out of your building wardrobe.
//SHOP OUR PICKS//
Stay handsome: The grooming guides for your 20s, 30s, 40s, and 50s.
Lace-Up Boots
Footwear is the foundation of any great outfit. While bad shoes may not necessarily be a deal breaker, they will have you playing from behind the rest of the night.
While fashion matters when it comes to footwear, function and durability are right up there, too.
Think about it. In college, you could get by with a few pairs of sneakers and some flip-flops for the shower, but those won’t fly in the real world. A good pair of sophisticated leather boots will not only look sharp, they’ll be able to withstand those nights in your twenties that get a little crazy.
When we talk about boots, we aren’t talking about work boots with chunky soles and reinforced toes. In your twenties, less is more. The toe of the boot shouldn’t be too bulky. It should look more like a dress shoe than a work boot.
A nice rounded toe is going to dress down better than a chiseled toe, while pointy or square toes are just a no-no. A plain or capped toe is always a good option. For a bit more flair, go for a wingtip boot. It dresses up as well as it dresses down.
A good boot will become your go-to shoe. If you want to go even more sophisticated, a wingtip boot is a good option that can be worn with jeans or slacks. The boot should come just above the ankle. 5-6 inches in height is a good range for how tall the boot should be.
The most important part of the shoe, though, is the sole.
Look for Goodyear welted soles. They will cost a bit more but over the years will allow you to replace the sole, rather than buying a brand new boot. Leather soles are more sophisticated than rubber, but if you’re worried about inclement weather, your local shoe repair person can easily put a thin piece of rubber over a leather sole.
For a smart casual Friday look, pair it with chinos, and oxford and blazer. When your college buddies are in town for a weekend, boots class up your standard jeans and t-shirt look.
//SHOP OUR PICKS//
Slim Sweats
Just because you’re out in the real world doesn’t mean you have to be totally buttoned up at all times. There’s nothing wrong with looking more adventurous, especially in your twenties, and a great pair of slim fitting sweatpants allows you to look youthful, stylish, and comfortable all at the same time.
Unlike the sweats you had in college that you wore over shorts on your way to your intramural football game, these sweats should be much more fitted.
Look for pants with…let’s call it “ease” at the top – no need to put on a show for the world – with a leg opening that becomes more fitted and narrow. Look for sweats with clean lines and no embellishments. Less is more when you’re trying to class up sweatpants. A nice pair of trim sweatpants with a white oxford and clean white sneakers is a great boozy brunch look. The great part about slim sweats is they are still appropriate to wear to workout, and they have the added bonus of telling the ladies that frequent your gym you’ve got a bit more style than the rest.
//SHOP OUR PICKS//
Stylish Wallet
So you’ve got your degree, you’ve got a job, and for the first time you’ve got money coming in on a regular basis. It’s time to get a nice place to put that money. No, we’re not talking about a checking and savings account (though you should get those, too!).
We’re talking about wallets.
Sometimes it’s the little things that make all the difference. It’s time to retire that duct tape wallet you made in high school and upgrade to something more sophisticated.
The home guides for your 20s, 30s, 40s, and 50s.
Stay away from bulky billfold wallets; they are a slippery slope to the dreaded Costanza wallet, overstuffed with receipts, cash, and loyalty cards spilling everywhere.
For most guys, a simple cardholder is all you need. A few slots for your ID, a couple credit cards and a small slot for cash. If you live in a big city like New York, you may find yourself needing cash a bit more for your favorite coffee shop or bar that’s cash-only. Thankfully, a number of brands make simple wallets with a zip closure, giving you more room for cash than a card holder.
Leather is a great choice for material. It’s durable and will age well over time.
As for color, black is standard, but medium brown is a great option if you want something subtle but will show a bit more wear and character. If you want a bit more personality, don’t be afraid of some color. There are great blue, green, even orange or red leather wallets that are masculine as well as interesting. They can make for great conversation pieces when you go to buy a young lady a drink at the bar *wink wink, nudge nudge*
//SHOP OUR PICKS//
How to upgrade your wardrobe in your 20s
Don’t go shopping for everything all at once. Instead, phase in clothes made in higher-end materials and a slim cut. You’ve got to give up the casual hoodies that were a staple in your teen years eventually (there’s not many jobs where they’re encouraged in the dress code), so start experimenting with more interesting textures and clothes that fit closer to the body now.
Make these wardrobe updates in a way that feels gradual, rather than abrupt (which will be easier on your bank account anyway).
You don’t want to all of a sudden go from faded bootcut jeans to a three-piece suit. You can, however, go from faded bootcut jeans to dark-rinse, straight-leg denim without causing too much whiplash for the friends who see you every day. From there, the jump from jeans to cords or khakis doesn’t feel so scary. Later, graduating from the khaki pants to a pair of wool trousers (or that suit) will be even easier.
This move works across your whole wardrobe – maybe next you’ll swap out your dirty old sneakers for a pair that’s fresh and clean (and clearly not meant for the gym, track, or court). The hoodie for a v-neck sweater.
Do this with all your clothes, and you’ll slowly amass a closet full of great-looking, quality clothes, without anyone accusing you of going all Zoolander on them.
Essential accessories for me are always socks. As long as they’re colorful or interesting they’re allowed in my drawer.
It’s starting to change a bit though, as my workplace doesn’t require a tie but I like to wear one. I find myself often browsing the Tie Bar for a new tie/tie bar to throw on once and a while to work.
Both of these. I tend to stay with solid polos and chinos for work, so the socks are a great “pop”. And casual ties on Fridays with jeans are the way to go!
During my 20s, I’ve stocked up on:
– plaid shirts (a hipster staple)
– slim dark jeans in indigo and black (both smart AND casual, with black adding some edge to it)
– non-denim jeans (a great middle ground for denim and chinos)
– boots (they add some edge to a wardrobe, whether they’re Chelseas, chukkas or brogues)
– v-neck or henley tees (great as is or layered)
– outerwear (whether they’re bombers, bikers, truckers, etc, they set the vibe of the outfit)
These are all solid picks!
What do you go for in regards to non denim jeans? I’ve found a few pairs of twill trousers. But I’m trying to find something different to wear in the summer months rather than jeans or chinos or shorts.
Not a whole lot when it comes to criteria, but if anything, I’d like the colors like my usual denim (e.g. black and navy) plus some neutrals like khaki and olive and I’ll probably get something in an unexpected color soon enough.
Oh, and stretch too! Love Joe’s Jeans for this type of thing.
What do you go for in regards to non denim jeans? I’ve found a few pairs of twill trousers. But I’m trying to find something different to wear in the summer months rather than jeans or chinos or shorts.
During my 20s I was wearing flared jeans because back in the early 2000s that was all the rage, with like paint stains on them.
hahahha, I had jeans like that too 🙂 They’re cutoff shorts now
I’ve just got a navy blazer and I’m loving it.
Joggers are not really for me, I’m more into chinos.
I’m looking into getting a pair of brogue boots next, that’ll be my winter purchase.
I’d add in a smart coat for your 20’s if you’re in a colder climate. Or even some dark denim, I’m partial to selvedge.
Both are good additions!
Navy pea coat has so much mileage in it
You know it, it’s pretty much all I use in the winter months.
I’ll second that – my peacoat is the workhorse of my wardrobe and I am still looking for a lighter jacket that looks as good as it does and is so versatile.
Hmmm… What do you think of:
a) cotton/nylon bomber
b) lightweight lambskin leather jacket
c) dark denim trucker
d) a cotton version of a peacoat
Let me know if these help.
Cotton bomber is on the list – I just need to find one I like that is not all blousy and 90s looking. Very easy to get the bomber wrong
Have you tried a m65? They’re pretty versatile not as smart as a peacoat but I reply on one in the warmer months.
I’ve stocked on:
-Blazers that can be both dressed up and down
-Dark wash and Black jeans
-OCBD’s
-solid Vneck and crew neck t shirts
-Nice boots and dresses shoes
-Socks…tons of them
Love the last point. After pairing way too many singles lately, I’ve decided to do a full sock purge this weekend and start fresh (exciting plans, I know..)
Pay for your boots now or keep buying similar pairs later. I made that mistake and am now perusing a good forever pair that I can keep having resoled like my Bean boots.
I’m 27 and I finally got a decent wool navy blazer. I had been relying on thrift store options that were probably more poly than wool (it’s hard to tell when the label is ripped out).
OCBDs are my favorite wardrobe staple. I’ve got them in white, blue, yellow, and green. They are a workhorse and they can be dressed up and down. And damn it if they aren’t some of the most comfortable things I own.
Personally I’d recommend a pair of dark brown wingtips before the boots. Like the OCBD, they can be dressed up or down and they will fly in almost every situation except the most formal ones.
Lolz at the “Costanza wallet” reference.
It even looks like you’re wearing an OCBD in your avatar pic, is that right?
It is right. They’re probably the shirt I wear the most.
Accessories: suede tubular belt, cheap sunglasses from giant vintage, vintage pocket squares, silk ascots, wool or raw silk bow ties cuz they look better without a blazer and don’t mess with the work id and lanyard. A couple quirky enamel pins for denim jacket.
Accessories: suede tubular belt, cheap sunglasses from giant vintage, vintage pocket squares, silk ascots, wool or raw silk bow ties cuz they look better without a blazer and don’t mess with the work id and lanyard. A couple quirky enamel pins for denim jacket.
I definitely stock up on ties. As a law student preparing to finally enter into the work world, ties are essential.