How To Dress-Up Your Jeans feat. Jelani Johnson

December 1st, 2014

Wearing jeans with a jacket and tie is one of those high-risk/high-reward moves. It’s easy to make it look disjointed, but if you nail it, it can be a very suave look that can take you just about anywhere.

Here our friend Jelani shows us how to pull it off.

Evening Sleek


Got a cocktail party or a work event to go to? This is a sure win.

Firstly, the silhouette of the jeans is very important. They should be slim – not skinny – and be consistent with the cut of the jacket. Essentially they should be cut like the trousers that would make this look a suit.

It’s okay to have a small cuff at the bottom, just make sure the jeans are tapered close enough to the ankle to make sense with a sharp dress shoe, like these custom “murder monks“. If you don’t have a pair of jeans with the right fit, consider taking a pair or two to your tailor, you won’t regret it. Also, consider the wash of the jeans. If you’re going for a sleek evening look with a black or charcoal jacket, try a jean in a cool medium grey like the pair here.

  • Essential Black Jacket by Articles of Style ·
  • Black glasses by Warby Parker ·
  • Grey wool tie Vintage ·
  • 1″ tie bar from TheTieBar ·
  • Black lizard belt by Trafalgar ·
  • Grey jeans by Red Cotton Denim ·
  • Black ostrich monkstrap shoes by Awl & Sundry
  • · Classic White Broadcloth Shirt by Articles of Style

White Broadcloth Shirt

Dressing Smart


Trying to look like a smart guy who’s got his sh*t together? Nothing does that better than a collegiate inspired look comprised of a tweed jacket, oxford shirt, and selvedge denim. The finishing touches tie it all together, too: vintage knit tie, wool cardigan, suede loafers, retro frames.

Personally I like the clean look of a jean that is hemmed with no break but that can be a commitment at the tailor shop since there’s no going back. If you want to keep a little length in your jeans, go with a clean roll when dressing them up.

As mentioned, dressed-up jeans can make for a very versatile look. This is another example of an outfit that is appropriate for a wide variety of occasions, day or night.

  • Brown donegal tweed suit jacket ·
  • Wool block-stripe tie Vintage ·
  • Forest green wool cardigan by Uniqlo ·
  • Indigo denim jeans by JBrand ·
  • Brown Suede Loafers by Ralph Lauren
  • · Blue USA Oxford Shirt by Articles of Style

Blue USA Oxford Shirt

Dad Jeans Updated


If you’re really trying to flex some style muscles, you can break out an unexpected classic: the vintage washed Levi’s, otherwise known as “dad jeans”. The best part about these jeans: they were $15 in a vintage shop.

This is not for style rookies, it’s a look that can easily “miss” and look silly. The trick here is to avoid anything stuffy. Even the “dressy” elements should lean toward the casual/lighthearted side: unstructured sport coat with a check pattern, silk tie with a bold pattern, flowy pocket square, suede shoes, ring belt. It’s dressy, but far from corporate.

For more “dressed up jeans” looks, you can always use our Style Guide. Simply filter by “Jeans” + “Business” or “Business Casual“.


Baby Blue Hairline Stripe Shirt

Thanks, as always, for reading and special thanks to Jelani for taking time out of his busy Hollywood producer lifestyle to model for us.

Yours in style,

Dan Trepanier

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