How to Tailor Your Jeans

May 19th, 2011

I’ve been slammed with design school and other projects, so the website has taken a back seat for a bit. Today, just a quick tip.

The jeans you pair with rugged boots or high top sneakers shouldn’t be the same jeans you wear with sharp lace-ups or sleek loafers.


    In order to properly “dress-up” your jeans, they should be similar in shape to your trousers, if not slightly more tailored (slim, staight & slightly cropped) to make up for the casual nature of denim fabric.

    In my opinion (of course), this is how a suave man does “business casual”.

    Yes, they are a little on the short and narrow side (these haven’t fully stretched-in yet). With a narrow leg opening (here, approximatelt 15 1/2″ across) this length creates a more flattering leg line, not to mention shows off the shoes. Keep in mind, as always, that I am a stylist – not a banker, so if you’re place of business is a little “stuffier”, you might want to look for (or tailor) a  jean a little wider, and a little longer. But keep them dark, unembelished and with minial contrast in the stitching.

    Best part about this – remove the jacket & tie and go straight from the office to a night out.


    Thanks for reading.

    Yours in style,

    Dan Trepanier

    Photography by Alex Crawford.

    Shop Custom Menswear Made in America


    Click Here, We’ll do the Rest

    • Lucile Galuska

      I’m impressed, I must say. Really seldom do I run into a web site that’s both educative and exciting, and let me tell you, you have hit the nail on the head. Your idea is extraordinary ; the issue is something that not enough people are talking intelligently about. I am very happy that I happened across this.

    • Phil

      I would tailor some jeans way back in the 90s and never liked how you lose the aging around the hems. You know? Looks too clean. Any secret to not making them look tailored?

    • Ishaan

      what’s with all the hate on your comments nowadays SB? Keep doing your thing homeboy!

    • lunchmeat317

      Oh, dear….I can’t agree with this look. The skinny jeans stopping well shy of the shoe heel is a very specific look; it’s not one I would wear, but I can see how it might suit you. But the white socks? Why, man, why?

      The socks draw attention to your puddle-jumper hems, which really ruins the line of the pants themselves. For the good of humanity, please, wear dark dress socks. If you must draw attention to your feet and ankles, at least pick out a nice argyle pattern. Please and thank you.

    • Anonymous

      According to every rule of tailoring since the dawn of time, your pants are just too sort. I completely get the look, and I actually even like it (on others not myself), but there is no doubt they are sartorially incorrect.

      • SB

        I’m not sure which dawn-of-time-tailor you are referring to. Prior to traditional trousers becoming the norm men wore knee breaches – which hit at the knee and were worn with hose.

        I hem my own pants, to my own preference.

        Thanks for reading,

    • Anonymous

      Great look you’re sporting there. Some great jeans

    • Anonymous

      Great post, The pictures are wonderful =)

    • Corey

      Excellent full rollover on the vest. It’s IN the details.

    • Carina

      Beautiful clothing doesn’t make a fine gentleman any more than beautiful feathers make a fine bird

    • IlGattopardo

      I know spring has just arrived but I can’t undestand why you’re wearing socks with that look. It just seems odd. Loose the socks (and the vest) and you’ll look perfect.
      All the best.

    • Arsene

      Really like the the fact that what makes this look so appealing is not just the individual pieces, but how the cut and fit really create the look. ^fist-pump

    • Jason

      Very sharp well tailored look


      • SB

        Thx Jason.

    • Maurice

      Do wider lapels look edgy? To me this is the wider lapel look from the 1970’s modernized for today.

      • SB


    • Zach Raymond

      This is teh mullet look. Business in the front party in the back.

      • SB

        Not sure that’s exactly right, but I get what you’re saying.

        Thanks for reading,

    • JMRouse

      Maybe it’s fear of being accused of wearing highwaters when I was in middleschool,but I might have gone with jeans a tad longer. hah Otherwise great look Dan!

    • Parker

      Nice work Dan.
      I heard you once dunked on a 6″8 center. That’s awesome bro.

      • SB

        True story. I had my share of moments above the rim…back in the day. There’s video to prove it, lol.

        Thx for reading.

        • TO

          Post that….Dan Hoopmixtape

    • Anonymous

      this reminds me of the news anchor without pants! Dressy up top, relaxed below haha

      • SB

        lol..”did you get the invite to the party? The pants, the pants party?”

    • Mondo Fantastico

      Funny…I work at a bank and these guys wear some of the most ridiculous jeans (like mom jeans for men) you can imagine. I’m still waiting for the day one of them shows up in some stretch acid-wash joints with stirrups.

      As far as the look…sharp…but a little to dressy up top for my personal taste with jeans. I’d most likely go with a notch lapel and more texture over pane or stripe on the jacket. I like to wear a less structured jacket with jeans…otherwise I always end up feeling a little too stiff up top and relaxed down below……hmmmm…the reverse actually sounds more interesting…Ha!


    • Leonardo

      Is a great balance between casual and tailoring, and this always results in a great outfit.

      • SB

        Thanks Leonardo.

    • mcr

      Huge fan of this look Dan, definitely gave me more of an idea on which jean to purchase to wear for a more business casual look. Not to mention the hemline of a jean, love the length and fit of the jean.. Not too narrow or too short for me. Thumbs up!

      PS. Just curious what the brand of the jeans are?

      • SB


    • Gary-A

      @Jim – Nice suggestion. Vests without shirts are so hot right now.

      @SB – Dig the color combo a lot! I’ve been thinking about getting another pair of APC’s (or similar style, dark selvedge. Any suggestions for a guy with TBTYH? hah) for just this purpose – dress one up and beat the hell outta the other.

      Related: Your thoughts on washing/caring for selvedge?

      Semi-Related: You’ve got some guts. I cringe inside when I think about wearing jeans with anything that could even be misconstrued as white socks. Too many poorly-dressed-dad images flashing through my head.

      • SB

        Washing selvage – after 6 months of hard wear, dry clean.
        Thx for reading.


    • T. Zagraniski


      Great tip! I appreciate you taking the time just to do this, even with everything else you have going on. Thanks very much.

      – TLZ

      • SB

        Thx brother!
        I hope all is well.

    • vali

      wow, this is spot on! hope this is just a tease for a post with more dressing up jeans outfits!

      • SB

        Now it is! :)
        Thanks for the post idea, coming soon.


    • cam

      Dan, you failed to mention the most important thing….the brand of jean

      • shaqueeda

        my boo anit fail shit !!!!!!

      • rismomax

        I second this comment….I want those jeans!

      • SB

        J Crew.

    • AFJ

      Why not brown loafers?

      • WJA


      • SB

        Because that would be expected. Thanks for reading.


    • Oli

      I love that windowpane suit. Are the jeans the same APCs you were wearing before?

    • Jim

      Like the tips about the jeans but I’m not sure about the overall look; just seems mismatched with all the dressy items up top and then casual below the waist.

      • Knucklehead

        I also think the matched jacket and vest makes the rest of the outfit out of synch. I think this look would be better with a contrasting vest in a casual fabric or a dark colored cardigan. But, as SB says, that’s just my opinion based on my personal style.

    • TO

      They are hemmed straight across though and not on an angle (a la dress pants) right? Would you ever consider that with jeans? And btw, what’s the make of jeans featured? Thank D.

      • SB

        They are hemmed straight, although an angled hem on dressy denim is a great idea!
        The jeans are JCrew.
        Hope all is well TO. Got your email, responding soon.

        • TO

          Looking forward to it! Thanks man, and all is well.