Best Outfits for Home-Based Entrepreneurs

We know you love your PJs, but here are some good reasons (and excuses) to jazz up your home attire. 

Images loading...

Tips from Sasha Westin

"Being a home-based entrepreneur makes your image extremely important because you are solely responsible for representing yourself. Who would you rather do business with - an entrepreneur that looks incredibly successful or one who does not appear to prioritize her business?"


-- Sasha Westin, Fabuliss

Photo Credit: Reaction Studios

Think About Your Top Layer

A top layer like a well-fitted blazer provides you with a polished look while demonstrating that you respect your audience.


-- Sasha Westin, Fabuliss


J.Crew velvet blazer, $168;

Photo Credit: Courtesy of J. Crew

Statement Necklace

Use a statement necklace to frame your face, express yourself and differentiate yourself from others.


-- Sasha Westin, Fabuliss


Octagonal Statement Necklace, $328.00; Kate Spade


Photo Credit: Courtesy of Kate Spade

A Genuine Smile

Nothing is more attractive than a warm handshake accompanied by a genuine smile, whether you are meeting with your peers or potential customers.


-- Sasha Westin, Fabuliss




Photo courtesy of Kinga/

Photo courtesy of Kinga/

Slim Profile Tote

A slim profile tote will reduce bulk while housing your handbag and essentials for customer meetings.


-- Sasha Westin, Fabuliss


Michael Kors Monogrammed Tote, $198; Nordstrom

Photo Credit: Courtesy of Michael Kors

Tips from Claudia Patel

"Dressing well, even if you are a home based entrepreneur, is critical. It not only sparks a sense of confidence, but at the same time, helps separate the idea that 'bedroom to home office is a crawl away' mindset – making you more productive."


-- Claudia Patel, Fashion Designer


Photo Credit: Melisa Teo

Invest in a Cardigan

Make the cardigan wrap a staple. It’s a great way to smarten your casual look, especially when you have unannounced visitors knocking at your door.


-- Claudia Patel


Open Cardigan, $49.88; Ann Taylor

Photo Credit: Courtesy of Ann Taylor

Dress to Step Out

Ditch your pajamas for something casual and smart. A cute blouson top is comfy enough for wearing around the house, yet you will be errand ready when duty calls, or an urgent meeting with a client pops up on your calendar.


-- Claudia Patel


Paisley Pintuck Blouson Tee, $59.50; Talbots


Photo Credit: Courtesy of Talbots

Stick to the Nude Philosophy

Why wear make-up if you don’t need to? Best to keep your skin make-up free, with just a light lip gloss. Your skin will thank you for this.

-- Claudia Patel


Bare Escentuals 100% Natural Lipgloss, $15; Bare Escentuals

Photo Credit: Courtesy of Bare Escentuals

Make Work Staples Your New Accessories

By work staples, I mean work staples, like pens, papers, and paper weights. Choosing colorful and vibrant work accessories will not only dress up your work area, but your mood as well and I can’t tell you enough how much this will lend to your overall productivity (not to mention style).


-- Claudia Patel

Paper Mate InkJoy 300 Ballpoint Retractable Pen, $6.49 8/Pack; Staples

Photo Credit: Courtesy of Paper Mate

Tips from Sally McGraw

"Career experts recommend dressing up for phone interviews even though potential employers can't see your business-class duds. The same principle applies to solitary entrepreneurs: Dressing well affects your confidence, productivity, and overall demeanor as you work. Wearing smart clothing can help create focus, and the ritual of getting dressed is a great way to start the working day."


-- Sally McGraw of Already Pretty and Strong, Sexy & Stylish



Photo Credit: Michael McGraw

Plan Outfits Ahead of Time

If you take an hour on Sunday to assemble ensembles for the coming week, you'll be a lot less likely to reach for those sweats day after day. Hang completed outfits in your closet - accessories and all - for easy access.


-- Sally McGraw, Already Pretty




Photo Courtesy of crystalfoto/

Photo Credit: Courtesy of crystalfoto/

Consider Tunics

The long over lean dressing formula is a fantastic smart-casual alternative to jeans and tees, and works beautifully for home-based entrepreneurs. Tunics paired with leggings, skinny pants, or other slim-cut bottoms create a modern, flattering silhouette on many figures, and this combination of pieces is as comfy as PJs.

-- Sally McGraw, Already Pretty


Eileen Fisher Jersey Tunic & Ankle Leggings, was $98, now $65; Neiman Marcus

Photo Credit: Courtesy of Eileen Fisher

Investigate Ponte Knits

Ponte is a double-knit interlock fabric that has stability and firmness in addition to flexibility and softness. This means it can hold its shape when used in dresses, blazers, and more structured pieces, but also remain pliant and forgiving. It's a fabulous option for home-based entrepreneurs interested in looking sharp while staying comfortable.


-- Sally McGraw, Already Pretty

Ponte Knit Slim-Leg Pants, was $79, now $39.99; J.Jill

Photo Credit: Courtesy of J.Jill

Invest in Comfortable Flat Boots

Tall boots add sass to virtually any outfit, and flat styles are ideal for entrepreneurial types. We all know that working from home actually means racing around the house, running errands, and dashing out for the occasional business meeting. A polished pair of flat boots will help you look sleek and chic while remaining mobile.

-- Sally McGraw, Already Pretty


Zara riding boots, $90;

Courtesy of Zara

Tips from Nichelle Pace

"Having a home office does not mean you should not be ready for last minute meetings, lunches, etc. Already being dressed appropriately will save you time and you don't want to scare off the delivery man if you get frequent packages as I do. Treat your home office like you would a corporate office. Get dressed."


-- Nichelle Pace, founder of Stylemom

Photo credit: Charles Wilmore, Wilmore Photography

Remember a Certain Look Can Change Your Attitude and Mood

Looking confident is part of sounding confident, whether you are talking with a client over the phone or communicating through email. You want to be on top of your game, and feeling good about yourself can give you that edge. Plus, many businesses now skype.


-- Nichelle Pace, Stylemom


Celeste Striped Pencil Skirt, $98; Anthropologie

Photo Credit: Courtesy of Anthropologie

Stylish Jeans

Stylish jeans are the new entrepreneur work uniform, wide leg or straight. You can throw on a blazer or a fitted button up with your jeans and be ready for a meeting in a pinch. Add a pair of fun heels to add extra chic to your casual work look.


Suggested Brands: Calvin Klein, Gap, Vintage Revolution, Citizens for Humanity


-- Nichelle Pace, Stylemom


Citizens of Humanity Elson Medium Rise Straight-Leg Jeans, $158; Saks Fifth Avenue

Photo Credit: Courtesy of Citizens of Humanity

Get Out of Those Slippers

Yes, sometimes you can get in a rut of over-indulging in the comfort of your home office environment. Get out of those p.j.'s, sweats, and slippers, and get dressed. This includes your feet. Fun cozy flats are functional, comfy, and will complete your entrepreneur work look.


Suggested Brands: Me Too, Michael Kors, Nine West.


-- Nichelle Pace, Stylemom

Crisp, $79; Nine West

Photo Credit: Nine West

Don't Forget Your Hair

For a low maintenance and professional look, I would recommend a shorter bob, a style with less layering. Short hair is a big trend this year, especially amongst celebrities. When styling, you have the option to add a style cream and let your hair air dry or you can blow dry your hair for a clean, polished finish. 

-- Ashley Stone, Founder of Beauty Entourage and Salon Alexander




Jennifer Jeanne Patterson is a freelance writer and author of 52 Fights. She lives in Minneapolis with her husband and three children. Find her blog at Unplanned Cooking.

Related: Stress Busters for Entrepreneurs

Don't miss out on MORE great articles like this one. Click here to sign up for our weekly newsletter! 


Photo Credit: Parsons Photography

First Published February 8, 2012

Share Your Thoughts!


Post new comment

Click to add a comment
Member Voices
Shoes & Accessories
Woman of Style and Substance
Swim & Lingerie