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.

21 Things Men Should Never Wear

In this video, I talk about the 21 things men should never wear! These are the things that’ll curl your toenails, and offend even your grandmother. Just don.do.it.

 

1. Gaudy Rings & Pinky Rings

2. Too Much Cologne
Too Much Cologne Ashley Weston

3. Socks with Sandals

4. Sandals In General

5. Shorts That Go Past Your Knees

6. Old dirty shoes
Dirty Shoes Ashley Weston

7. Cartoon printed boxers

8. T-Shirts with Brand Logos

9. Baggy, Ill-Fitting Clothing

10. Tank Tops
Tank Tops

11. Skinny Jeans

12. Pointy & Square-Toed Shoes

13. Deep V-Neck T-Shirts
Vneck

14. Big, Square, or Monogrammed Belt Buckles

15. Leather Bracelets

16. Elongated Shirts

17. Soul Patch
Soul Patch Ashley Weston

18. Crocs

19. Earrings and Facial Rings

20. Short-Sleeve Sweaters

21. Dress Shoes with Tennis Shoe Soles

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!