What to Wear in New York: Packing List

15 Cute, Simple Outfits to Fall Back On When You Have *Literally* Nothing to Wear

Getting dressed in the morning might be the least of your worries at the moment, but before you know it (at least I'm hoping)(please)(I'm begging), we'll be back to our normal lives and regular routines. That means you'll be returning to the struggle of finding the perfect outfit – which, usually involves changing six times and then inevitably putting back on the first outfit you still hate, but not before your entire room is covered in clothes. Fun!

Fortunately, there are some tried-and-true outfit formulas that can help you speed the process along the next time you get dressed up. Ahead, I've rounded up a ton of cute simple outfits for you to fall back on when you find yourself with nothing to wear. Again.

How Older Men Should Dress (Simple Style Advice Over 40) · Effortless Gent

There’s a lot of advice on the internet about how older guys should dress. If you’re a man in your 40s, 50s, or even older, what should you wear? Which mens fashion rules apply to you? Does your style have to change? Are you now required to wear dad jeans and cargo shorts?

The subject of menswear can get tricky as you age: your body’s changing, you get stuck in your ways, it’s harder to wear stylish stuff like skinny jeans or a graphic tee without feeling like you’re trying too hard or “dressing too young”.

But, really, it doesn’t have to be super confusing, especially if you follow a few style principles and create your own dress code that looks good and you’d happily follow.

In this article, we’ll cover those style principles with the goal of making sure you have a well-curated, sharp-looking, and age-appropriate wardrobe that works now, and for decades to come.

How should a 40 year old man dress, exactly?

Let me answer your question with another question: Have you seen the movie, Crazy, Stupid, Love?

If not, it’s an early 2010s rom-com that, according to Wikipedia, “…follows a recently separated man who seeks to rediscover his manhood and is taught how to pick up women at bars.”

What? That’s an awful one-line summary for an awesome rom com that was waaay more than that.

Anyway, Cal, a middle-aged, soon-to-be divorcé (played by Steve Carell) who, in an attempt to pick himself up after days of self-loathing and pity, becomes inspired and then coached by a younger, smoother-talking, swag-filled Jacob (played by Ryan Gosling, of course).

Ultimately, he reinvents himself.

There was a montage during Cal’s reinvention that displayed him in some pretty impressive outfits for a guy his age and in his situation. It was picture-perfect proof that guys, no matter their age, have no excuse for not dressing well.

Cal’s style (post-intervention) provides great examples of how the classic rules of clothing apply to any age group and never go out of style.

Which style category are you in?

Most men ages 40 and up seem to fall into one of these three categories:

They really get what they’re doing They’re stuck in some previous decade they enjoyed most They stop caring completely

Ironically, lots of men in this age group also have the level of success their younger counterparts are striving for, and are more comfortable in their own skin than guys in their 20s and early 30s, who are still figuring shit out.

Basically, you have the money and the self-confidence to dress better. So why aren’t you?

Cal (Carell) before his style improvement in Crazy, Stupid, Love… Fully dadded out (VIA WB)

Style Tip: Ignore men’s fashion. Just follow these guidelines.

If you’re unsure where to start, why not follow in the footsteps of our friend, Cal? I can be your Jacob, making sure you don’t commit any age-(in)appropriate men’s clothing no-nos.

Let’s start with these guidelines and general principles:

Fit and proportion are the most important things

Lots of middle-aged / older men wear clothing that’s either too snug, or way too oversized. It could be that you’re wearing clothes that once fit (but don’t anymore), or you assume bigger clothes are more comfortable.

So, a few things about this:

Well-fitting clothing doesn’t mean “uncomfortable” As we age, our shape and proportions can change, and to look and feel good, we have to wear clothing that complements those changes

Maybe you had a V-shape in your early 30s—wide chest and back, slim torso—but now, in your mid-40s, you’re not as muscular up top, and you have a bit of a belly. The clothes that fit you well back then won’t fit you comfortably now.

Maybe you were overweight when you were a younger man, but managed to drop the fat and maintain a slim physique all these years later… but you’re still wearing size XL shirts and your pants are falling off your waist.

Some of Cal’s (Carell) outfits after working with Jacob (Gosling) in Crazy, Stupid, Love (via WB)

Whether you’re skinny, overweight, or just right, you need to buy clothes that fit your current proportions.

But how do you find clothing that fits, exactly?

You have to try lots of stuff on. I know, it’s a chore, but that’s the only way to start understanding how clothes should fit.

Go to the mall and grab the size you think you are. Then grab one size up and one size down. Try them all on. Take a photo in the mirror. See what feels right. Bring a friend or your partner if you have to, and ask their opinion about how something fits.

Clothes should allow you the freedom to move without being oversized. It’s a balance.

If you prefer trying stuff on at home (I know I do), give Amazon Prime Try Before You Buy a shot. You can order a bunch of stuff, and they give you a week to try stuff on at home. Keep what you like, return the rest, and only get charged for what you keep. It’s pretty great!

Amazon Try Before You Buy (Prime Wardrobe) Choose up to 6 items per box, try everything before you buy, and only pay for what you keep! Free and easy returns. Start Browsing

Classic Casual Wear Over Fashion Trends

Fashion is a funny thing. Take the Dad Jeans trend:

If a 22-year-old wears them, he’s trendy and fashion-forward.

If a 44-year-old wears them, he’s frumpy and a terrible dresser.

Since you’re reading Effortless Gent, I assume you’re going for a modern version of classic style… a smart casual look with outfits that are a few notches above the jeans-and-sweatshirt default, while still being comfortable without feeling overdressed.

That sound about right?

If so, stay away from most trends and fashion-forward looks, especially if they’re an ironic play on “old man” style. Leave that experimentation to the younger guys.

So unless you’re a rock musician like Jagger or Slash, no ultra skinny jeans (a fitted pair of jeans is good, skinny, not good).

Unless you’re an eccentric movie star who makes questionable financial decisions like Johnny Depp, maybe chill with the scarves and limit your accessorizing.

For the most part, stick to neutral colors and more somber color schemes in general (looks more sophisticated in an outfit).

Great celeb style to emulate? Here are just a few examples:

Not sure if your jeans are skinny jeans? Wondering if you can still wear your favorite graphic tee? Thinking you have to trade in your casual sneakers for dress shoes?

Don’t panic. Keep reading. I’ll have suggestions for you later in this article.

Want awesome sharp, casual style? The Devil’s In The Details