The Renewed Rise of the Casuals

Jess Li
Jess Li
Jul 2 · 3 min read

Season Three is a direct-to-consumer apparel brand that makes boots for humans. Check us out at .

In March of this year, made headlines after announcing the rollout of a new, relaxed dress code making suits and ties optional. Goldman is not alone: , , , , , , , , , , , , , , , and are among the many companies that have loosened restrictions on dress codes in the recent past. Across the board, young employees continue to show their desire to effortlessly transition from their professional to personal lives through their fashion and lifestyle choices.

Over the last 20 years, various workwear trends have come and gone. Wall Street banks, for example, relaxed their dress codes in the dotcom age, only to reverse course once the bubble burst. Given the fleeting nature of trends, workplaces have reasonably been wary of embracing the fashion of the moment. More recently, though, firms are shifting their viewpoints. In the unrelenting race for talent, firms are willing to acquiesce to dress code modifications in order to retain and attract top performers. In a recent , the majority (61%) of respondents answered that a business’ dress code would negatively influence their image of that workplace. So as the demand for workplace comfort increases, more and more companies are making the necessary changes to avoid losing employees.

This trend goes beyond attire, as the demand for modern, attractive, and comfortable workplaces is the driver behind successful co-working spaces like WeWork, where members enjoy stylish perks, such as nitro cold-brew coffee on tap. Companies are also making changes that transcend the physical office. Across industries and geographies, ‘Corporate America’ is offering more work arrangements. Contemporary accessibility to laptops and smartphones fosters an “always-on” atmosphere that has supplemented and allowed for more flexibility. After all, flexibility seems to be the magic ingredient to a happier lifestyle. According to a , 78% of employees reported that flexible work arrangements made them more productive, and 73% intimate that flexible work arrangements increased their satisfaction of work. Together, these work / life adjustments trend towards a concept dubbed the ‘,’ which presently, is some of the most important and exciting research being conducted at MIT. These efforts to meet employees where they’re at, with more considerate scheduling, better pay, and conscientious leadership show that firms can make the necessary changes to improve employee satisfaction without sacrificing productivity.

Despite structural shifts towards a more casual work environment and more flexible schedules, traditional fashion is failing to meet the needs of a changing workforce. The hurdle for the everyday worker is a wardrobe overflowing with drab styles designed for the static nine-to-five job and not enough of the fashionable staples that embody the present moment. The modern worker needs increased functionality in their attire because their dynamic lifestyles demand it. Someone working 40, 60, or even 80 hours a week might want to seamlessly flow between appointments in their packed schedule — from spin class to the museum, to drinks with friends, and to side hustles in between. The future of workwear focuses on the flexibility of one’s complex lifestyle; creating garments that occupy multiple spaces in a person’s wardrobe. This thought is incorporated into every product we design at Season Three.

Season Three

For hikers and (social) climbers.

Jess Li

Written by

Jess Li

Harvard 🎓 | IBD @ Morgan Stanley| VC @ RDV (General Catalyst), F3, GFC | Tech Strategy @ (YC W19), Elpha (YC S19) | Distance Runner 🏃‍♀️

Season Three

For hikers and (social) climbers.