You just turned 30. Which means you’re a proper grown-up now. Work’s going alright; you can finally afford not to live on a diet consisting solely of pot noodles, but you’re certainly no baller. And while your mum no longer cuts the crusts off of your fish finger sandwiches, you’re not quite ready to retire to the drawing room with your Labrador Cecil in the evening, clutching The Daily Telegraph and sporting your favourite smoking jacket.

But how to 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?

Rather than domineeringly telling you exactly what to wear now that you’re approaching proper manhood, let’s run down some of the items that you categorically shouldn’t be wearing. Even if you do feel young at heart.

1. Chunky Skate Shoes

To any skating enthusiast that came of age in the early noughties, owning this beast of a sneaker was crucial to mastering ollies and kickflips in your quest to trump Tony Hawk. Now? Not so much.

Sure, back then they were painfully cool, but then again, so were sneakers with teeny-tiny wheels on. Remember them? Yep. Rest in peace. The fundamental design flaw inherent to this type of shoe is that they look as awkward and clunky with skinny jeans as they do with a relaxed trouser.

It's time to ditch the chunky skate shoes

The Solution

Since the heady heyday of Jackass and Limp Bizkit, skate-inspired styles have gone mainstream. And while some can work, others need to be bailed on.

Chunky footwear and low-slung baggy jeans? Out. Streamlined, minimal silhouettes in premium materials? In. Vans Old Skool/Era CA and Converse Jack Purcells are fuss-free designs that complement drainpipes and ankle-swingers alike, while retaining some half-pipe credibility.

If, on the other hand, you’re ready to take a step up now that you have a little more disposable income, the likes of Common Projects and ETQ Amsterdam offer skater-esque silhouettes (complete with thick rubber sole) in luxe leathers and suedes that will instantly upgrade your everyday looks.

Men's Minimal Leather Low Top Trainers Outfit Inspiration lookbook

bally ss15mango man 2015whistles aw15h&m 2015next autumn 2015burton aw15m&s autograph aw15express autumn 2015river island aw15el burgues aw15cadillac aw15bensimon aw15

Key Pieces

  • Vans Old Skool Winter TrainersVans Old Skool Winter Trainers
  • Lacoste Straightset TrainersLacoste Straightset Trainers
  • Adidas Originals Stan Smith White & Black TrainersAdidas Originals Stan Smith White & Black Trainers
  • Reiss 1971 Don Patent Leather Trainers SlateReiss 1971 Don Patent Leather Trainers Slate
  • Etq. Low Top 1 SneakerEtq. Low Top 1 Sneaker
  • Topman Converse Black Leather TrainersTopman Converse Black Leather Trainers
  • Common Projects Original Achilles Leather SneakersCommon Projects Original Achilles Leather Sneakers
  • Nike All Court 2 Leather SneakersNike All Court 2 Leather Sneakers
  • Jack Purcell Trainers WhiteJack Purcell Trainers White

2. Baggy Beanies

At some point circa 2005, beanies went from Usher-tight to oversized. It was a look that David Beckham himself wholeheartedly embraced and, as with most trends Golden Balls gets behind, it blew right up. Soon, any metrosexual worth his Swarovski ear stud and deep V-neck tee was opting for preposterously oversized headwear to top it all off.

“A slouchy beanie makes every outfit instantly sloppier,” says Brooke Philips, senior stylist at leading personal shopping site And she’s right – now that you’ve hit the big 3-0, there’s no room for this student halls brand of slovenliness.

Even Beckham fell foul of the slouchy/oversized beanie

The Solution

It’s not the beanie itself that’s the problem. It’s the baggy. Much more age-appropriate is a beanie that fits. “A snug-fitting cable or waffle-knit beanie does the same job,” says Philips. “It’s also warmer, more comfortable and looks sharper than a beanie with a lot of flop.”

Thom Browne offers particularly luxurious styles knitted from a mohair-blend for extra warmth, but you’ll find less spendy options at Selected Homme or high street favourites like Topman and Mango.

Men's Fitted Beanie Outfit Inspiration lookbook

baldwin aw15allsaints aw12illustrated example aw15ben sherman aw15reiss aw15m&s aw13selected homme jeans 2014mango man blacksmith aw14scotch & soda Amsterdams Blauw aw15mango man aw13Gant Rugger AW14mango man november 2014

Key Pieces

  • Gant Rugger Ribbed BeanieGant Rugger Ribbed Beanie
  • Acne Studios Nils BeanieAcne Studios Nils Beanie
  • He By Mango Wool-blend BeanieHe By Mango Wool-blend Beanie
  • M&s Collection Ribbed Beanie HatM&s Collection Ribbed Beanie Hat
  • J.crew Melange Knitted BeanieJ.crew Melange Knitted Beanie
  • Thom Browne Camel BeanieThom Browne Camel Beanie
  • Selected Homme Cable Knit BeanieSelected Homme Cable Knit Beanie
  • Reiss Nake Cable Knit Beanie Hat NavyReiss Nake Cable Knit Beanie Hat Navy
  • Topman Khaki And Black Mini Ribbed Roll BeanieTopman Khaki And Black Mini Ribbed Roll Beanie

3. Novelty Knick Knacks

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

Hopefully you’ll have had the sense to leave trunks that proudly declare your societal status as a ‘Beer Monster’ or baggy boxer shorts that come emblazoned with the warning ‘In Case Of Emergency, Pull Down’ far, far behind you. At mum and dad’s. Along with those saucy Max Power posters.

It's time to ditch the comedy boxer shorts

The Solution

Underwear should cover your buttocks, not make you the butt of jokes. “[Plain] boxer briefs combine the best of both worlds, [they’re] suited to most body types and hold everything in place without drawing too much attention,” says Olie Arnold, Deputy Style Director at Mr Porter.

As for colours, we’d suggest steering dark for, er, ‘sanitary’ reasons, as well as saving yourself the almightily boring task of washing white and dark undies separately. Japanese masters of basics Uniqlo guarantee unbeatable value for money, but for superior quality and comfort, look to Derek Rose or Schiesser.

Stylish Men's Underwear

Beckham Bodywear for H&MBeckham Bodywear for H&MDavid Gandy for M&SDavid Gandy for M&S

Key Pieces

  • Gant Solid Trunks Pack Of 3 Atlantic BlueGant Solid Trunks Pack Of 3 Atlantic Blue
  • David Gandy For Autograph 2 Pack Stretch Supima Cotton HipstersDavid Gandy For Autograph 2 Pack Stretch Supima Cotton Hipsters
  • H&m 3-pack Boxer ShortsH&m 3-pack Boxer Shorts
  • Schiesser Karl Heinz Cotton Boxer ShortsSchiesser Karl Heinz Cotton Boxer Shorts
  • Calvin Klein Underwear Stretch-cotton Boxer BriefsCalvin Klein Underwear Stretch-cotton Boxer Briefs
  • Derek Rose Ethan Stretch-micro Modal Boxer BriefsDerek Rose Ethan Stretch-micro Modal Boxer Briefs
  • Calvin Klein Button Fly Boxer TrunksCalvin Klein Button Fly Boxer Trunks
  • Sunspel Egyptian Cotton Low Waist TrunksSunspel Egyptian Cotton Low Waist Trunks
  • Uniqlo Men Supima Cotton TrunksUniqlo Men Supima Cotton Trunks

4. University Merch

Let’s face it, you aren’t Head Boy anymore. Head of Sales, Head of Marketing or Head Shelf Stacker maybe, but not Head Boy.

So, slip off that university hoody, take it outside, read its last rites and bury it. Deep, deep in the ground. The only person that cares you went to Oxford is your mum.

The only person who cares you went to Oxford is your mum - ditch the uni hoodies

The Solution

Let’s not be hasty, there’s no need to banish jersey entirely just yet. Compete with the big boys in a simple sweatshirt, sans logos. A crew neck boasts more versatility than a hoody from a styling point of view; grey, navy or black sweatshirts can be made casual Friday-appropriate with a white button-down and slim tailored trouser, or pub-appropriate with a white tee and pair of slim jeans.

Again, Uniqlo is tough to trump on budget jersey basics, but Albam, Acne Studios and A.P.C. take this wardrobe mainstay to a more premium level. A plain, well-fitted hoodie still has its place though: “Where you went to uni should no longer define you,” says Philips. “However, a plain, fitted hoodie is still a stylish weekend choice when teamed with slim jeans.”

Men's Plain Sweatshirts and Hoodies Outfit Inspiration lookbook

next autumn 2015Boglioli AW15zarabanana republic pre aw14hackett aw15vince aw15burton aw15jaeger aw14burton aw15saba aw15el burgues aw15j.crew september 2014

Key Pieces

  • Acne Studios Flinton Crew SweatAcne Studios Flinton Crew Sweat
  • Uniqlo Men Sweat Long Sleeve ShirtUniqlo Men Sweat Long Sleeve Shirt
  • Reiss Cart Seam Detail Sweatshirt IndigoReiss Cart Seam Detail Sweatshirt Indigo
  • James Perse Supima Cotton-jersey Raglan SweatshirtJames Perse Supima Cotton-jersey Raglan Sweatshirt
  • Topman Washed Black SweatshirtTopman Washed Black Sweatshirt
  • A.p.c. Loopback Cotton-jersey SweatshirtA.p.c. Loopback Cotton-jersey Sweatshirt
  • River Island Dark Grey Stitched Sleeve HoodieRiver Island Dark Grey Stitched Sleeve Hoodie
  • Uniqlo Men Sweat Full-zip HoodieUniqlo Men Sweat Full-zip Hoodie
  • Eleven Paris Bamako HoodieEleven Paris Bamako Hoodie

5. Cliché Band T-Shirts

This is a potentially divisive one for any proud musos, so we’ll clarify what we mean exactly: repping that niche Krautrock band you saw in Ghent is all well and good (in fact, we applaud your dedication to the cause); but insisting on wearing that tired, misshapen Green Day T-shirt you splurged far too much uni loan money on at Reading in 2004 is the mark of a man trapped forever in a state of adolescence.

Time to ditch the cliche band tees, fellas

The Solution

Don’t get us wrong, we’re not condemning the band tee entirely. But we do have a few caveats when it comes to wearing one: think about both what you’re wearing it with and the occasion you’re wearing it for before dusting off that trusty Ramones or Sonic Youth tee.

“Two rules should be considered,” says Arnold. “Firstly, keep it simple, and secondly, keep it casual. A slim jean and Converse with your favourite tee are perfect wears for a lazy weekend or spot of Sunday lunch.”

Probably the worst thing you can do with a band tee is try to dress it up: throwing brogues and/or a blazer into the mix will instantly transform you from ultra-cool to ultra-supply-teacher. Not so rock ‘n’ roll.

The right way to wear a band t-shirt - MenASOS 2015

Final Word

Turning 30 needn’t mean joint bank accounts, mortgages and desperately convincing yourself staying in is the new going out. But it does mean smartening your act up a little.

What would you toss as you bid farewell to your twenties? Any tips on how to best dress your age?

Drop your thoughts below.