I just got back from a great trip to Buffalo to speak at an entrepreneur’s retreat for women. I was about two hours south of Buffalo on Lake Chautauqua near Jamestown. It was lovely to get away and the women I met were incredible. My speaking presentation was all about navigating the new workplace post-pandemic. One of the things I spoke about was pairing tailored with soft to create a more relaxed and comfortable look that is still professional in appearance. As I describe it, the tailored pieces elevate the more relaxed and casual pieces while the casual pieces take the more tailored or professional pieces down a notch. As a result, it strikes a balance in that sweet spot between the two.

I shared the five looks below to showcase some ways you can achieve this look for yourself. Check them out below.


tailored and soft

In this first look, I styled a pair of joggers with a blazer. I’m not suggesting you style the joggers you wear to binge Netflix’s Halston that have the nacho cheese dip stain. The pandemic has introduced a whole range of jogger styles and you definitely want to go with a style you would NOT wear to bed. This pair from COS is a tailored pants/jogger hybrid and captures that sweet spot I was referring to. I styled the pants with a cotton, linen blazer from J.Crew that I styled over an ivory cotton sleeveless blouse from Frame, brushed silver drop earrings from Nordstrom, and light blue block heel sandals from Franco Sarto.

Outfit #2

tailored and soft

Next, I styled this tailored midi-skirt from M.M. Lafleur in a relaxed way by pairing it with a linen button-up shirt from Frank & Eileen. I finished the look with metallic accented sneakers from Cole Haan and horn drop earrings from M.M. Lafleur.

Outfit #3

tailored and soft

Styling an easy top or sweater with tailored pants is probably the easiest way to embrace this style of dressing and it’s likely you were dressing this way long before we went into lockdown. I styled these Theory pants with a relaxed viscose summer sweater from Paise. I finished the look with metallic flat mules from Kurt Geiger and a tortoise necklace from Zenzii.

Outfit #4

tailored and soft

In this look, I am using the jacket to add structure to this very easy dress. When I was speaking last week, I had two outfit options. One was wearing a very easy knit jumpsuit with a white tailored blazer. The jumpsuit basically feels like wearing an adult onsie and the jacket created a more professional look. In the end, I went with a different look and decided to wear the jumpsuit casually on its own at the retreat a day earlier but it’s pretty incredible how just a blazer could make such an easy and comfortable piece look professional.

In this outfit, I styled this black, sleeveless midi-dress from Nordstrom with a summer tweed jacket from M.M. Lafleur. I finished the look with red ankle strap block heels and black glass drop earrings from Kendra Scott.

Outfit #5

tailored and soft

A relaxed cardigan with a tailored look is certainly nothing new and it’s an easy way to pair tailored with soft. I styled this jumpsuit from 11 Honoré with a black cardigan from Eileen Fisher. I finished the look with leopard low heel pumps from Franco Sarto and the same horn earrings from M.M. Lafleur as in the second look.