I remember Google searching men’s outfit ideas in my young 20’s.
My wardrobe was on life support, and for the first time I had some money to purchase decent clothes. The problem was I didn’t know where to start.
My sense of style took a long time to develop. My parents didn’t raise me as the kid who always had cool new outfits. I basically wore whatever I got for my birthday and Christmas.
What I discovered over time was that there are certain clothing items that are timeless. It doesn’t matter how many years go by, they’ll always be in style, and you’ll always feel condfident wearing them.
Then you have all the experimental purchases that you look back and wonder what the hell you were thinking.
Take it from me – everything on this list will be in style for a long time.
The fit (tight/baggy) and the patterns (flannel shorts) may change, but the general look will stand the test of time.
1) White Low-Top Chucks
Converse shoes are a timeless classic.
They work for a multitude of occasions. A quick trip to the market, a casual night out, or even the gym. These shoes are versatile and will always be in style.
2) Vest
Having a decent vest unlocks a variety of different looks.
You can go casual with a hoody for a warm layer, or wear it with a nice button-down for a night out at dinner. I recommend a goose-down vest or a vest with some puffiness. Try to avoid thin vests that lay flat like a t-shirt.
3) Chukka Boots
These shoes have become the go-to for many men around the world.
Chukkas are perfect for a night out to dinner with friends or even to bars. They give you a more polished, mature appearance and work with almost any outfit.
4) Black Chino Pants
I wear my black chinos more than any other pants.
They’re a step up from denim jeans and work with almost any outfit. You can wear them with a white t-shirt for an elevated casual look, or a button-down and coat for a night on the town.
5) Blue Suit
This is probably the most essential item on the list.
Blue suits work for every semi-formal occasion. You can wear them to weddings, work, or dinner parties. You can also wear just the slacks or coat to mix things up.
6) Joggers
Every man should have a nice pair of joggers that he can wear in public.
Nobody should be running around in baggy cotton sweatpants, but if you’re like me and don’t want to wear denim jeans on an airplane, wear some joggers. You can even wear them with a t-shirt and a flannel for an elevated casual look.
7) White Leather Nike’s
I like the leather Nike’s for days when the weather isn’t great, so cloth shoes don’t make sense.
If the ground is wet and you need a casual outfit, these should be your go-to.
8) Silver Watch
If you don’t have a decent watch, make this a priority.
I couldn’t imagine not wearing a watch out. Silver is the most versatile, so start there. You can get a good-looking watch for cheap.
When I was in my young 20’s I didn’t have much money for clothes, so I went to Ross and got two watches for like $35 each. They lasted me a couple years and nobody could tell they were from a discount store.
9) Flannel Button Up
I’d be surprised if someone reading this didn’t own at least one flannel shirt, but if that’s you, I highly recommend getting one asap.
Flannels are great in cooler months and for casual occasions. Plus, they come with the added benefit of keeping you warm.
10) Tan Shorts (5-inch seam)
Tan shorts work well with most colors and are a classic look. I prefer a shorter inseam on shorts these days.
The inseam is the length of the seam on the inside leg of the pants.
If a 5-inch seam is too short for you, keep the cut above the knees.
11) Leather Boots
Every man needs a decent pair of boots. This is non-negotiable.
Boots are great for inclement weather, and with the right pair, you can still look dressy when you go out on a snowy night. There are plenty of different styles for every personality.
If you’re on a budget, I recommend Khol’s. They have a decent selection under $100.
12) Solid Black/White T-Shirt
Not all t-shirts are created the same.
I’m not talking a Hane’s classic t-shirt. You need a premium t-shirt, preferably made of synthetic blend material.
We all like a different fit, but if you have a belly, it can be hard to find a plain t-shirt that looks good for a night with friends.
I recommend Bylt Basics. Their shirts fit tight around the arms and shoulders, give some room around the waist, and they have a comfortable length.
13) Modern Loafers
I’m not talking about the old-style loafers that your grandpa wore.
I’m talking about the nice slip-on shoes that can be worn with everything from a casual fit to a suit. And no, they don’t have to come with tassels.
I got my favorite pair from Express. Black leather with white soles is a versatile look.
14) Bomber Jacket
Classic, timeless, and multifaceted.
A bomber is good with jeans, joggers, dress shirts, t-shirts, you name it. They’re always in style, and I especially like wearing a bomber jacket with a hoody underneath.
15) Brown Leather Dress Shoes
You need the right shoes for your blue suit, and these are the ones.
Brown leather dress shoes can be worn with many outfits, but they shine best when worn with a suit.
I love when the shoes fade from a dark hue to a lighter one. You can also go for the wingtip if you’re feeling flashy.
16) Quarter Zip
Going for the classy but casual look? A quarter zip sweater never fails.
There are infinite options, so find the style that best suits you and rock it. Some quarter zips are outdoor jackets, some are casual pullovers, and some are dressy.
I like my quarter zip to have a relaxed fit, but if you have an athletic build, don’t be afraid to show off your physique with a tighter fit.
17) Golf Polo
This might not be for the hipsters and trendy guys, but golf polos are classic.
They are fantastic for hot days because they usually have synthetic material that wicks sweat and keeps you cool.
If you’re attending a daytime event requiring more than a t-shirt, golf polos are a perfect choice. These days there are tons of stylish options too.
18) Hoody (for Going Out)
We all have hoodies, but not everyone has a hoody for a night out.
You can’t be meeting friends for drinks in your sweated-out cotton gym hoody, so you need to get a nice one. I have a black zip hoody from Oakley that fits snugly and looks great with chinos and chucks.
Just remember this, if it’s 100% cotton and bulky, that’s not the look.
19) Dry Fit Gym T-Shirt
There comes an age when every man must stop dressing like a high school kid.
For me that age was about 28, which was entirely too late. I always wore cutoff sweat shorts and cutoff shirts. Then one day, I looked around the gym, and realized I was the only one my age still dressed like a college kid.
Get yourself some decent gym shirts. These days oversized shirts are in style.
20) Gym Shorts 5in Seam
People can get by with a cutoff shirt but not with raggedy shorts.
Also, having comfortable gym shorts makes your workout much more enjoyable.
Something else to note – science has proven that confidence in your exercise clothing improves the quality of your workouts. When you feel better about your appearance, you push yourself harder.
Essentially they’re saying if you buy better gym clothes, you’ll get in better shape (not even kidding).
21) Rain Jacket
Here’s another purchase I waited entirely too long for.
Rain jackets are so clutch when the rain is coming down hard, especially if you have dogs to walk or you walk to work. This isn’t so much a fashion purchase as it is a lifestyle purchase.
Once you get one, you’ll wonder how you managed without it.
22) Solid White Dress Shirt
Most men have a white button-down dress shirt, but if you don’t, you need one. This is a staple for so many outfits.
More important than the shirt is how it fits!
Too many men are still wearing not fitted dress shirts. A proper fit should be snug around the chest, shoulders, and arms, but provide room to move around.
If the sleeves of your shirt look like parachutes, it’s time to upgrade.
23) Goose Down Jacket
Look, I know some guys aren’t “puffy jacket” guys, and that’s fine, but wearing your Carhartt to dinner looks cheesy.
Get yourself a stylish down jacket (not too puffy) that can be worn around town and keep you warm in the winter. The one I have from Patagonia is incredible. The wind can’t cut through it, and it keeps me warm even in negative temps.
24) (Respectable) Sandals
If you’re still rocking Target sandals, it’s time to upgrade.
I love wearing sandals. Why would anybody want to wear shoes on a hot summer day?
But here’s the thing. Sandals work in many situations, but cheap-looking sandals make you look underdressed. The quality of your sandals matters, and you don’t want to look like a slob.
25) Short Sleeve Button Up
This is the go-to shirt for almost all casual outings in the summer months.
You can wear it with shorts and sandals, pants and shoes, or even a swimsuit to the pool. You can usually find an attractive pattern and show off those arm muscles too.
One Response