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Styling the Boardroom Boss Capsule Collection

Styling the Boardroom Boss Capsule Collection

How to build a capsule wardrobe that will take you from workwear to weekend ready!

Interested in curating a capsule wardrobe but unsure how to streamline your style from workwear to weekend ready? With elevated wardrobe essentials you can transition your 9-5 uniform into effortlessly chic outfits, fit for evening outings and weekend excursions. 


Welcome, Boardroom Bosses. If you’ve landed on this page after completing the Encircled Capsule Wardrobe Quiz, your main wardrobe focus is work appropriate clothing that can easily be incorporated into your personal life, from dinners in the city to exploring the latest museum exhibits. Read on to learn how you can style the Boardroom Boss Capsule Collection and get the most out of your wardrobe.

If you’ve not yet taken the Capsule Quiz, click here to do so! In just a few minutes you can learn your ideal capsule wardrobe type and view a curated collection of clothing tailored to your lifestyle. Along with a shop-able collection you’ll receive the Minimalist Wardrobe Workbook, a step-by-step guide that walks you through the process of defining your style, provides tips on auditing your closet and helps you build the perfect capsule wardrobe that suits your needs.


As a Boardroom Boss, your life consists of 70% work 30% play, and a wardrobe that transitions from weekdays to weekends is required to get the most wear out of your clothing. In order to maintain a capsule wardrobe, where your closet generally consists of 30-50 pieces per season, dressier versatile pieces are needed. You live a busy life and are dedicated to your work, but love to explore the city and try new restaurants so finding clothing that can work for all occasions without needing two completely separate styles and closets is a must. 


In order to establish a streamlined wardrobe for both your work and personal life, you’ll need to focus on building a wardrobe that consists of elevated essentials that can easily be dressed up for the office or down for a chic, more casual look. To achieve a stylish yet simplified wardrobe you’ll require: 

  • Versatile workwear pieces that can be mixed and matched with one another for endless styling opportunities. Think of neutral trousers or timeless blazers that pair well with other classic workwear outfits or can be styled with more casual clothing like jeans and cozy sweaters. 
  • Elevated basics like a high quality t-shirt and cardigan that can be worn for running weekend errands or layered with office attire for comfortable work appropriate outfit. 

To mix and match clothing without hesitation and begin the process of creating go-to looks and outfit formulas, we recommend sticking to neutral colours and incorporating your preferred colour palette to add a complimentary pop of colour. If you’re unsure about your colour palette, have a look inside the Minimalist Wardrobe Workbook to get you started.


As a first step in finding inspiration towards curating your ideal capsule wardrobe, we’ve put together our favourite Boardroom Boss outfits incorporating both versatile workwear pieces and elevated basics to show you how each item can be styled from the boardroom to brunch.


1. The Revolve Dress

Revolve dress with trousers and blazer

(@phdinclothes wearing the Encircled Revolve Dress)

An elegant workwear dress is a classic wardrobe staple. Pair your favourite dress with heels or loafers and a blazer for a dressy look with minimal effort. Versatile in styling options, our Revolve Dress is also a multiway piece that can be worn 6 ways! Reverse the neckline to choose between a cowl neck or boat neck and wear it as a top, tunic or dress.


2. The Unblazer

The Unblazez styled with jeans and a white dress shirt

(@thenordnest wearing the Encircled Unblazer)

A blazer is a timeless staple and a must-have for any workwear wardrobe. An elevated essential that can be paired with trousers and a blouse for your next big pitch, or dressed down with dark denim jeans and kitten heels for a night at the museum, this layering piece is seasonless and thus ideal for a capsule wardrobe. Comfy like a cardigan but chic like a suit, The Unblazer can be seamlessly transitioned and styled across events without ever feeling the stuffiness of a structured suit.


3. The Dressy Sweatpant

The dressy sweatpants styled with a blazer
(@msbeltempo wearing the Encircled Dressy Sweatpant)

Off to work in sweatpants? Yes! With flattering wide pleats and ruching at the ankle, the Dressy Sweatpant provides the comfort of a sweatpant without sacrificing style or elegance. Perfect for the office alongside a blazer and heels, these not-so-basic sweatpants give the appearance of trousers while being comfortable enough to lounge in.


4. The Comfy Dress Shirt

The comfy dress shirt styled with the everyday wrap skirt and the dressy leggings

The perfect marriage between a tailored shirt and your favourite PJs, the Comfy Dress shirt is all business without sacrificing any comfort. With a front pleat and versatile, flattering length, this comfortable dress shirt can be tucked in and dressed up with a skirt or pair of trousers, or worn alongside leggings or jeans to take you from workwear appropriate to weekend ready.


5. The Comfy Puff Sleeve Cardigan

Comfy puff sleeve cardigan styled with a dress and jeans

Great for layering over dresses, blouses, t-shirts and jeans, cardigans are a versatile wardrobe staple that work for any occasion and compliment all types of dress codes. Better than a sweater, The Comfy Puff Sleeve Cardi can be worn with a matching belt for an elegant wrap style cardigan or worn open with your favourite layer underneath. With a fitted cuff and hemline that hits at the hip, wear this cardigan at the office and keep the comfortable layer as you head to happy hour.



6. The Comfy Wide Leg Crop

Comfy wide leg crop styled with a t-shirt, jacket, heels and mules

(@hersimplesole wearing the Encircled Comfy Wide Leg Crop)

With a lifestyle that consists of 70% work and 30% play, your capsule wardrobe requires cool pieces perfect for the warmer months that can be transitioned into the fall for longer lasting wear. Perfect for the summer, The Comfy Wide Leg Crop will have you thinking you’re headed to your next networking event in sweatpants as the 4-way stretch fabric is comfortable enough to lounge in but dressy enough to feel put together. With flattering pleats and two pockets, these versatile bottoms are ideal for those days when comfort is needed without sacrificing style.


7. The Dressy Sweatshirt

Dressy sweatshirt styled with trousers
(@thenordnest wearing the Encircled Dressy Sweatshirt)

A sweatshirt you can wear to work? Yes please! The Dressy Sweatshirt is a dressier take on the classic sweater, allowing you to dress comfortably for work while being equally equipped to take it slow and lounge all weekend. A dressier basic and versatile workwear item, this sweatshirt offers a wide neckline for a boatneck or off the shoulder look that can be paired with leggings for an elevated weekend outfit or styled with a blazer for cozy office wear.


Feeling inspired to start building your Boardroom Boss wardrobe?


Let us know in the comments below which elevated essential is your go-to staple and how you love to style it from 9-5 workwear to weekend ready.


Travel Essentials. Encircled creates versatile minimalist clothes with the everyday traveler in mind. Each piece is Made in Canada, out of sustainable, and eco friendly materials.

1 comment


such a great content.

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