8 Things ALL Guys Should STOP Wearing In Their 30s

You just turned 30 or you’re in your 30’s and have decided to get it together on the clothing front. Congratulations because this officially means you’re now a proper grownup. While you may not be be hitting your peak professionally or financially yet, you’re definitely on the way, which means you should be taking your clothing and appearance a little more seriously.

So where does that leave your wardrobe? How do you walk the tightrope that is post-twenties dressing without looking like an over-the-hill has-been, or worse – a textbook case of early mid-life crisis?

These are some of the items that categorically shouldn’t be in your rotation in your third decade. Even if you do feel young at heart.

 

Dirty or Faded Anything

You’re too old to have an excuse for dirty clothing and shoes. You’re not out in the playground anymore, so your excuse for having dirty or terribly worn out anything is just laziness.

Graphic Tees

There are two exceptions when it comes to wearing one: You’re headed to watch your favorite sports team play or you’re going to a concert. Outside of these two situations, wearing a graphic tee communicates your someone who can’t get over the fact he’s no longer in his twenties.

Dirty, old or worn out shoes

No self-respecting man should be walking around in old, dirty shoes. Ever. Also, did you know it’s one of the first things women look at and can be a real make it or break it when it comes to first impressions?

Baggy anything

Unless you think to yourself, I’d like a more relaxed fit with these because that’s a silhouette I’d like to go for with this outfit, then you shouldn’t be wearing anything ill-fitting. The days of you wearing clothes because they were gifted or somehow found their way into your wardrobe by happenstance are over. A man in his 30’s should know what he’s going for and should nail it.

“If a guy shows up wearing ill-fitting pants or a big shirt, game over,” said every woman on planet Earth.

White socks and novelty underwear

Nothing says this guy dresses like a grade schooler more than white socks. Replace them with literally any other color – starting with black, blue and gray, and you’ll be on the road to adulthood!

Novelty underwear is a rite of passage for most men. When you’re a teenager, it’s the go-to Christmas gift for relatives intent on finding skivvies that’ll give you a chuckle. But we’re still not laughing.

Hopefully by now, you’ll have had the sense to leave the trunks that declare you a ‘Beer Monster’ or baggy boxer shorts emblazoned with the warning ‘In Case Of Emergency, Pull Down’ far, far behind you.

We even did a super in-depth article on the best men’s underwear out there if you need to check that out.

Shorts

Cargo shorts, especially. The one type of shorts you can wear are chino cloth shorts, but frankly, now that you’re older, shorts should mostly be worn near bodies of water in the form of swim trunks. Instead, grab some chino pants and roll up the hem (or get them hemmed to be a little shorter) and you’ve got something breathable and much more age-appropriate.

Flip Flops/Sandals

Unless you’re at a body of water, get rid of them.

Unkempt Haircuts

An adult ensures he always looks good, and that definitely goes for your hair.

16 Accessories Every Man Needs

These are, to me, the 16 accessories every guy needs to own, regardless of your age, occupation, and lifestyle. Some of these items you may not wear often, but there will be an occasion, as a grown man, when you will need them and you’ll be thankful that you thought far enough ahead to take care of them before it’s too late and you’re scrambling at the last minute. I’ve also included my favorites for each of these items below. But these points below are just skimming the surface compared to the much more through Men’s Essential Accessories Series I did recently.

Have questions? Curious what others think?

Join us in the comments section of the video above.

16. White Pocket Square

Like I’ve mentioned before, every man should have at least a grey suit. Even if you only wear it once every year, you’re going to need a suit. Along with that, looking well dressed is always about the details and a white pocket square is an easily overlooked item that really does make a big impact and it’ll only set you back a couple of bucks.

White Pocket Square Ashley Weston

$175 – Tom Ford Solid Classic Silk Pocket Square
$60 – Boss Solid Silk Pocket Square
$10 – The Tie Bar Solid White Cotton Pocket Square

15. Silver Tie Bar

This is another overlooked item. I talked about this in my article about the 12 Things Men Wear That Women Love, but a tie bar is something that adds that special touch to your outfit. It’s also so cheap to own so order it once and you’ll never think about it again.

Silver Tie Bar Ashley Weston$15 – The Tie Bar Silver Shot Tie Bar
$70 – J. Crew Sterling-Silver Tie Clip 

14. Solid Black and Navy Tie

These two ties will work for any suit you have in your closet, making them an absolute must have. Make sure the width of your tie complements your body type.

Black and Navy Tie Ashley Weston

$19 – The Tie Bar Grenafaux Tie (available in black and navy)
$60 – J. Crew American Wool Navy Tie
$60 – J. Crew American Wool Black Tie

13. Dress Socks

Get rid of your white socks. These socks can and should be worn as your everyday socks. If you need heavier duty, thicker socks for your job or because of the weather, there are plenty of companies that offer warmer versions.

Solid or Patterned Dress Socks Ashley Weston

$4 – Uniqlo Argyle Socks
$20 – Brooks Brothers Egyptian Cotton Jersey Knit Crew Socks
$15 – J. Crew Tipped Microstriped Socks

12. Sunglasses

Whether you’re a sunglass man or not, sunglasses are important because they’re going to protect your eyes from the sun, prevent you from squinting, which creates wrinkles around your eyes, and they can add a stylish, cool touch to your outfit. Check out my sunglasses story so you choose the right frames for your face shape.

Sunglasses 1 Ashley Weston 2

$415 – Tom Ford Snowdon Sunglasses
$98 – J. Crew Jack Sunglasses
$95 – Warby Parker Winston Sunglasses 

11. Baseball Hat

We all have those lazy days, myself included, where you just say F it, I’m gonna throw on a hat. When it comes to baseball hats I have very specific opinions about them so I shared some of my recommendations below.

Baseball Cap Ashley Weston

$48 – Gents ‘The Directors’ Baseball Cap
$22 – Flexfit Blank Snapback 2014

10. Black and Brown Oxford or Derby Shoes

Not only do these oxford dress shoes look great with your suit, but they also look nice with chinos, jeans, and trousers when you want to dress up a more casual outfit.

Black and Brown Shoes Ashley Weston

$395 – Allen Edmonds Carlyle Plain-Toe Oxfords
$750 – Prada Plain-Toe Bluchers
$175 – Johnston & Murphy Melton Cap Toe Oxfords

9. Black and Brown Dress Belts

Since you’re going to own dress shoes, you absolutely need to match your leather belt to your shoes.

Black and Brown Dress Belt Ashley Weston

$98 – Brooks Brothers Leather Dress Belt
$98 – Allen Edmonds Poplar Dress Belt
$25 – H&M Leather Belt

8. Weekender Bag

Everyone travels. Whether it’s to some exotic country, or across town, you’ll need to put your clothes in something AND trash bags are not an option. Like every accessory you own, it should not only serve it’s purpose, but look damn good at the same time. I have a whole article about weekender bags you should check out.

Weekender Bag Ashley Weston$965 – Frank Clegg Signature Travel Duffle (in black, chocolate or chesnut)
$800 – Killspencer Weekender 3.0 (in black leather or charcoal grey leather)
$115 – Everlane ‘The Dipped Weekender’ (in black/black, navy/black or reverse denim/black)

7. Dopp Kit

This item goes great with your weekender bag. Again, doesn’t matter if you’re traveling to another city or to the gym, a dopp kitt is essential because it’ll keep your grooming products organized and contained in a respectable manner.

Dopp Kit 1 Ashley Weston 2

$148 – Jack Spade Mason Leather Zipper Top Dopp
$300 – Shinola Travel Kit
$200 – This is Ground Tech Dopp Kit

6. Backpack or Briefcase with Detachable Strap

Depending on what you do for a living, if you live a more casual lifestyle or you’re a student, then a backpack is great. If you are in a more professional environment, a briefcase is best.

Backpack Briefcase Ashley Weston 1

Backpack

$800 – This is Ground Venture Regular Backpack
$210 – Cõte & Ciel Rhine Backpack
$120 – Aer Fit Pack Backpack 

Briefcase

$990 – Frank Clegg Zip-Top Briefcase
$895 – Shinola Slim Briefcase
$325 – Uri Minkoff Pebbled Leather Fulton Briefcase 

5. Casual or Dress Watch

Like the last point, which one you go with will depend on your lifestyle. Whether you’re a watch guy or not, any self-respecting man should own a watch or two.

Casual and Dress Watch Ashley Weston

Casual Watch

$7,000 – Rolex Submariner 114060
$3,400 – Omega Speedmaster Professional Moonwatch
$375 – Orient Diver Mako USA II

Dress Watch

$12,700 – IWC Schaffhausen Portugieser Automatic
$532 – Hamilton Intra-Matic Silver Dial Leather Watch
$195 – Tissot T-Classic Tradition Silver Dial

4. White Low Top Sneakers

Everyone has casual days, and white sneakers look so sharp on every guy regardless of your age or body type. If you’re really scared of wearing white, or think that it doesn’t look right, ease yourself into it with a nice low top lace-up black or navy sneaker.

White Sneakers 2 Ashley Weston

$370 – Acne Studios Adrian White Leather Sneakers
$75 – Adidas Stan Smith Sneakers
$65 – Converse Jack Purcell Classic Low Top

3. Boxer Briefs

All women find boxer briefs, specifically darker colors, so sexy on a man. And all men should be wearing them. Period.

Boxer Brief Ashley Weston

$26 – Exofficio Give-N-Go Boxer Brief
$13 – H&M 3-pack Boxer Shorts
$6 – Uniqlo Supima Cotton Boxer Briefs

2. Black and Brown Casual Leather Belts

Whenever you’re wearing jeans, chinos or shorts, throw on a casual leather belt because it’ll add a visually nice touch to your outfit.

Black and Brown Casual Belts Ashley Weston

$98 – Allen Edmonds Sun River Casual Belt
$295 – Salvatore Ferragamo Reversible Leather Belt 
$18 – H&M Leather Belt

1. A Quality Wallet

The things a man carries tells a lot about him and that’s no more true than with your wallet – check out my  article to the left for bifold, card cases, and phone wallet recommendations.

The below are only a few recommendations for bifold wallets.

Wallet Ashley Weston

$195 – Shinola Slim Bifold Leather Wallet 
$525 – Louis Vuitton Slender Wallet
$80 – Bellroy Low Down Wallet

Underwear – The Best Boxer Briefs

So let’s talk about your twig and berries, well… not really, let’s talk about the thing they go into – your underwear.

For a long time, men have viewed underwear as an afterthought. They were made of white cotton, reached up to your armpits, looked like you had a perpetual load in your pants and were bought in a 50 pack that’d last well into the next decade (or five, if you’re like my grandfather).

Other than shoes, underwear will impact your overall comfort more than any other garment. It doesn’t matter what you’re wearing on the outside, if you’ve got ill-fitting, bunching underwear, you’ll be annoyed and uncomfortable.

There’s a reason rough, uncomfortable clothing has been used for thousands of years as a form of torture.

The 2 Rules of Underwear Every Man Should Live By

Before we get into details, whether you go with my recommendations at the bottom of this page or not, these are the 2 rules for you should adhere to:

  1. Color is very important.
    Just like I mentioned in my 10 Style Mistakes Ebook regarding socks, you should never wear (or own!) white underwear. It’s gross looking, stains easily and reminds everyone of their father or grandfathers – and not in a good way. So stick with the dark, solid colors like black, brown, blue or charcoal gray and you’ll be fine.
  2. Avoid logos as much as possible.
    With some brands, including the ones I think you should own at the bottom of this story, it’s almost unavoidable, but please, please refrain from the ridiculous tommy logos and other crap like that. It’s just trashy.

Why You Should Only Wear Boxer Briefs

Underwear is an item of clothing that, if it’s doing it’s job correctly, shouldn’t be noticed. If you’re thinking about your underwear, even a second after you’ve put them on, that’s a problem.

There’s 5 major types of mens underwear

  1. Briefs
  2. Boxers
  3. Boxer Briefs
  4. Trunks
  5. (Technically, there’s thongs too, but… no)

Underwear should not do the following

  • Bunch or dig into your leg or crotch.
  • Cause any chafing.
  • Create visible panty lines (VPL’s) – this is a problem for men, too!
  • Turn your undercarriage into a cheese factory.
  • Remind someone of their meth-cooking father or grandfather.

In my experience, there’s only one type of underwear that has the least amount of the problems listed above: boxer briefs.

This is why I only recommend the best boxer briefs to all my clients. They’re the holy grail of underwear for the following reasons:

  • Most comfortable fit
  • Great breathability
  • Keep your plums secure
  • Flattering on any body type which is important because you want a woman to still think you look sexy when you’re just in your underwear
  • Won’t show through clothing and/or create VPL’s.

The Best Boxer Briefs

Here’s the brands I recommend to all my clients, based on their needs and preferences and what I’d consider the most comfortable underwear for men.

Ex-Officio Give N Go Boxer Briefs

Buy Them Here

ExofficioDropCrotchBig
There’s two different pairs from Ex-Officio that I recommend. The Give N Go’s are the ones my clients love the most. I’ve never seen them get so enthusiastic about a brand, but they really do love these.

Pros

  • Super comfortable, soft fabric.
  • Moisture wicking, breathable, synthetic blend material.
  • Generous, almost drop-crotch fit.
  • Very little stretching after extended use.
  • Extremely durable – I’ve seen them last over a year of regular wear with very little breakdown in quality or fit.
  • They don’t bunch.
  • I like the smaller waistband a lot, since it won’t be sticking out the top of your pants as much as some other brands.

Cons

  • They definitely look “sporty”, especially with the logo on the waistband.
  • If you prefer natural fibers, these are synthetic.
  • If you really like your plums held tightly in place, like with briefs, these will feel a little loose in that area. They feel more like boxers since the crotch is cut lower.
  • Some clients don’t like the odd angled stitching along the butt, they say it feels a little weird. But others say they prefer it.
  • The pocket access is through the side, which is the norm, but there’s another brand that I think does this better, which I’ll get into shortly.

Ex-Officio Give-N-Go Sport Mesh 6 or 9 Inch Boxer Briefs

Buy Them Here

 

ExOfficioSportMesh

These are similar to Give and Go’s, but my clients that didn’t like the regular ones, preferred these because:

  • The material is softer and silkier, but some of them also noted that this silkyness led to some bunching around the upper thigh as the day wore on. The best way to mitigate this is by getting the 6 or 9 inch versions depending on how tall you are.
  • The pouch/pocket in the front is smaller and tighter. These are their sport version. So if you really like your plums kept snug, these are better for you.
  • The downside is the loud colors and contrasting stitching. I personally think it’s a bit much, but my clients loved the fit and material so much that I’m willing to make an exception here because I want you to be as comfortable as possible. Just make sure to get the black ones with the red stitching – the other colors are way too loud.

Tommy John Second Skin Boxer Brief

Buy Them Here

TommyJohnLogoBlendIf my clients didn’t like the Ex-Officios, they gravitated towards these, instead.

Pros

  • Super soft material – the softest of the bunch, by far.
  • A top-loading pocket design that’s easier to use at the urinal.
  • Very breathable.
  • Comfortable waistband.
  • Snug applebag fit.

Cons

  • They’re pretty damn pricey – $30+ a pair.
  • They don’t retain their shape very well after extended wear, which can lead to a little bunching in the legs. To avoid this, I’ve had clients go down a size, but after a little bit, they’ll stretch out perfectly.
  • Not as durable. You’ll definitely have to replenish your stock more often than with Ex-Officio. These usually last about 8 -10 months with clients before they start wearing thin in areas.
  • They are made of thinner material, which is kind of sheer, which adds to the less-than-durable point I just mentioned.

H&M Cotton Stretch Boxer Briefs

Buy Them Here

HMBoxerBrief

I’m sure some of you are looking at the prices of my recommendations above and think I’m crazy. If caring about your genital comfort is a crime, then arrest me now!

My, let’s just say… “budget-conscious” clients prefer these over the other brands for the following reasons:

Pros

  • They’re cheap – $18 for a 3 pack.
  • Decent cotton fabric – not the best, but not the worst, either.
  • Doesn’t bunch as much.
  • No branding/logos- which is a big plus.
  • Did I mention they’re cheap?

Cons

  • Not as soft as other brands.
  • Not as durable and have a tendency to fade quicker than other brands.

Honorable Mentions

These just barely didn’t make the cut, but I wanted to include them as well. For their price, they’re great, but durability and longevity is always an issue at these price points. But if you really don’t want to pay a lot, these are right up your alley and hit the color and no-logo points perfectly. Just please replace them when they’re faded or holey. Typical usages was anywhere from 6 months to a year.

Uniqlo’s Airism Mesh Boxer Briefs

UniqloAirismBoxerBriefs

Uniqlo’s Supima Cotton Boxer Briefs

UniqloSupimaCottomBoxerBriefs

Kirkland Boxer Briefs

KirklandBlackBoxerBriefsUnderwear

That’s it, those are the honest-to-goodness best boxer briefs that I use with all my clients. So get your sh*t together and start wearing the most comfortable underwear for men – boxer briefs! Your psyche and gentleman’s sausage (that’s 4 euphemisms for male genitalia, if you’ve been keeping track!) will thank you!