Asking For a Friend: How to Talk to a Tailor post image

Men’s Fashion

Asking For a Friend: How to Talk to a Tailor

‘Asking for a Friend’ is our style advice series.

As you develop your personal style to incorporate traditional menswear, tailoring becomes essential. We understand if that causes some apprehension. But let us take care of you and you’ll see there’s nothing to worry about.

We offer alterations for free in all our stores, on almost every item. Drop in any time or make an appointment online. Our tailors are easy to speak with and ready to help.

Now let’s talk about tailoring pants. There’s not just one way to do it. You have to think about what kind of fit you want, and what kind of shoes you’re most likely to wear with the finished pants.

For inspiration, here’s how to make your favorite dress pants work three ways by tailoring them differently.

SHOP: Bonobos pants | Nordstrom Men’s Shop sweater | Eleventy coat | Common Projects Chelsea boot sold in-store only; inquire at these locations | all Chelsea boots

Slightly cropped

If you have Chelsea boots tell your tailor to give you a straight-across hem to wear with them. All boots have different heights, so bring them with you to get your fitting. If your boots are polished leather, try them with a suit and tie. Suede is better in a more relaxed mode, like we’re showing here. 


Tell your tailor to relax your pants and ask for a generous break. Most dress pants come unhemmed with a 37” inseam, with plenty of room for adjustments. Pair with clean sneakers, a long-sleeve shirt, and a polo buttoned all the way up to keep it from looking sloppy. Balance the relaxed pants with a sharp choice on top.

SHOP: Bonobos pants | Lanvin shirt | Vince mock collar | The North Face coatadidas shoes


The classic folded cuff is 1 ¼”. As for where it should hit, ask your tailor for the slightest break. You want a little sock or ankle to show. You don’t want the cuff to drag on top of the shoes—it looks unkempt and unintentional. To feel a little less buttoned-up, wear your suit with a turtleneck or sweater and some hybrid dress shoes.

SHOP: Bonobos pants | Bonobos sport coat | Ted Baker London pocket square | Nordstrom Men’s Shop turtleneck sweater | Timberland shoes

Photographer: Joel Ramirez

Assistant photographer: Chris Burrows

Stylist: Brenna Carlson

Assistant stylist: Lindsey Fish

HMU: Sarah Swaine

Model: Cameron Welch