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.

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    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.


    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“.

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    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

    Shop Custom Menswear Made in America


    Take me to the Shop

    • TO

      There are so many quirk pieces in the look “Dressing Smart” that I am enamored with that pull together an indeed very ‘smart’ retro/modern look- the different color striped socks being at the top of that list!

      Look “Dad jeans updated” is simply off the charts! What an astounding integrated mix of casual/formal Jelani x Dan…

    • tommyjohn_45

      I find it very difficult to keep shirts tucked in to jeans, which generally lends me to always go more casual an untucked, or with a cardigan. I have a long torso at 6’3″, coupled with lower cut waistlines, it just becomes a hassle.

      • Alex

        Also being 6’3″ with a long torso, the key with tucking in jeans is getting something with a medium rise. Most modern jeans are low rise. Also, due to having 24″ thighs, the Levi’s 541 Athletic is a good way to go for me.

        • tommyjohn_45

          Thanks, I’ll check those out!

    • AdamE

      Th3rd look should be e-mail to every politician, since they love to be photographed dressed down with the people in Dad jeans, but never can actually pull it off…

      That said, I keep my denim dark, but there are some great ideas in there. Love the tweed blazer in Look #2…

    • Olerud_4_Life

      Nice style bro. Subtle but inspirational. That third jacket is tough.

    • Brady

      I always love the light “dad” jeans with a brown jacket. All 3 looks are spot on