Privilege Blog

How To Build A Simple But Powerful Work Wardrobe, From Scratch


A couple of weeks ago, one of you asked for my thoughts on how to build a work wardrobe from scratch. Ah, work clothes. I remember them well. Above, the garb I wore to present to the New York Stock Exchange in 2008, just before the bottom dropped out of the market. I don’t think that was my fault.


Here’s an outfit from my 2011-2013 gig at a San Francisco Internet company. Context is all. Wasn’t showing a lot of bustline at the stock exchange, to be honest.

So, were I starting again, everything brand new, what to do? I’d want my clothes to be enjoyable and useful, simple to put together, flexible enough to inspire. I have to stress, what works for one woman won’t for another. No such thing as Five Items We All Must Own And Our Work Wardrobe Will Be Set Forever.

The simple but flexible work wardrobe requires you to make five primary choices

  1. Start with whatever gives you the most trouble. For me, that’s my feet. At base, a simple and wearable wardrobe depends on the shoes. Do you want to wear flats or heels, for the most part? If heels, how high?
  2. Next, simplicity requires that you decide whether you are going to wear mostly pants – with an occasional dress for special events – or dresses, with the occasional pair of pants for field trips and possible mud/rain/wind. There are physical factors here – your silhouette, how your body experiences comfort – and social ones – your relationship to gender traditions, the norms of your domain and your industry.
  3. It is at this point that you situate yourself somewhere on the Structured v. Flowy curve. Simple personal choice.
  4. You are ready to pick an interoperable color story.  I think the easiest to carry off is skin-toned based neutrals (i.e. earth-toned-AKA-yellow-undertones vs. stone & sky-toned-AKA-blue-undertones) complemented and accentuated by 2-4 accent colors. I have chosen gray/navy/black/white as neutrals, with purple, marine blue, olive, and mustard as accents. Someone with yellow skin undertones might choose brown/cream/black as neutrals, with coral, orange-red, pale yellow or sky blue accents. To learn about your degree of contrast in hair/eyes/skin, I will send you over to Imogen.
  5. Finally, what kind of accessory do you want to specialize in? Make these pieces big enough to register visually. Scarves? Bracelets and watches? Lapel pins? Dangling earrings? Bags don’t work for this purpose, we rarely walk around our workplace carrying a purse. Sue loves her French Kande jewelry. I chose earrings and a man’s watch. Focus.

I know. Choices are not easy. They require discipline and a conceptual framework, along with a willingness to constrain your impulses and shop from a plan. But oh the freedom come Thursday morning, when patience and forbearance wane. And the deep satisfaction when the new aubergine jacket goes perfectly with that old pair of well-tailored brown trousers.

A few recommendations on the actual clothes.

Shoes That Support Us, Flats & Heels

You can simplify your life profoundly by picking one heel height, two maximum. I like 2 1/4 inches myself or flats. Never let industry style, or the cultural imperative that women be sexually alluring, give you painful feet. I have bought various shoes, from Beautifeel to Birkenstocks (for casual wear), from Footwear Etc. in Palo Alto, California. Specialists in shoes without pain – turns out they sell online too.

Untitled #212

Ankle boots: brown & black, also comes in eggplant

Colorful: olive, purple suede (on sale, a few sizes left), red ballet flats

Workhorse neutrals: champagne flats, black heels,  brown patent flats (very inexpensive), black scribble pattern flats

Majority Pants vs. Dress Dominance (4 pairs of pants & 2 dresses v. 5 dresses & 1 pair of pants)

It’s not that you don’t know that there are dresses and there are pants. Only that by making a conscious decision to go one way or the other, primarily, you simplify life. Choose for your silhouette – stick with what works. You don’t have to reinvent the wheel every day.

Brands like Lafayette 148, Karen Millen and Marina Rinaldi for dresses, Theory, J. Crew, maybe even UNIQLO for pants are your friend. Add in a high-fashion item here and there if budget allows – a Dries van Noten dress, an Armani jacket – but let’s say you don’t need my help with that project now.

Untitled #211

Dresses: Maroon wrap, gray fitted, blue shift (on sale), gray not fitted (sold out by the time I got this post pulled together, others from the design line Peserico here), red fit and flare

Pants: Cropped and petite from J. Crew, camel windowpane from UNQLO for $29.99 (haven’t tried them but if they are good this is brilliant), skinny stretch wool from Theory – always a gold-medal pants line

Simplified Accessories

Some jangle-avoiding wrist options. I like that pink and green tourmaline necklace for someone in accounting, it reminds me of an abacus. And if you are ever going to buy a scarf, this is the year. Designers are exercising their art, the options are spectacular.

Untitled #210

Wrist: Tiffany cuff, gold and diamond bangle (comes in white gold too), Rolex Cellini

Necklace: Modern mother of pearl, sapphire and diamond pendant, lightweight gold layers, Bulgari pendant

Scarves: McQueen, Gucci, Etro. Artists all.

The Goalie’s Anxiety At The Penalty Kick

Right about now you might be howling, “What do you mean? I have a closet with 20 pairs of shoes, all different heights! I wear dresses AND trousers!”

I understand. Simplification is a harsh mistress. That said, optimizing might not be as difficult as you think. Many of the usual guidelines apply, including the one that says you can keep stuff that you love for no reason, and you can change your mind.

Decluttering And Investing Towards Love

  1. Clothes. Shove all the clothes you haven’t worn in the last 30 days to one side of your closet.
  2. Shoe Pairing. Line your shoes up and group them according to heel height. Now match the heel heights to the clothes you wear most often. If you want to simplify, this will become the kernel of your wardrobe.
  3. Love. Next, take a look at your favorite outfits, the colors, the pieces. You love them. Now move towards that love, towards their image, as quickly or as slowly as you like. This way you focus on growing rather than culling, at least at first. You’ll get there.
  4. Investing
    1. Find the designers and sources that work for you. Become a “regular.”
    2. I prefer to eschew big logos. I also prefer to buy sparsely, focusing on better design & materials.
    3. Look into vintage and “pre-owned” sources. I’m skittish about pre-owned clothes, but jewelry and accessories seem like fair game to me.

As a final tip, I will send you to my post on the Use Case Methodology. This is perhaps most applicable when you are changing jobs, but useful, I hope, in developing all kinds of complex, ground-up systems.

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42 Responses

  1. Great tips, Lisa! When I was still working in an office, I found that simplifying my wardrobe to a couple of silhouettes really helped de-stress those rushed mornings.

  2. I think your plan would work even for those of us who do not go to work in an office. I want to simplify my everyday wardrobe too–and think I have, but do need to focus again on it.

    1. @Susan D., I was thinking the same thing, time for me to reapply myself to the closet so that it works even better for me. I think that’s always the way, we focus, we blur, we focus, we blur.

  3. I’ve worked from home for the past 28+ years and I’m lucky if I even get out of my pajamas some days. This post makes me want to get a job in an office again just for the fun of putting together a wardrobe!

    1. @Leslie K, Don’t you wish someone would make really cool pajamas?;). I sure do. To the point where I imagine launching a line of flannel pajama pants in ikat and other cool prints. I won’t do it, but I do imagine it sometimes.

  4. This is great, Lisa! I’m in between jobs right now and anticipate needing to make some wardrobe changes, as my last position was in an extremely casual office environment.

    If you or any of your readers are ever interested in trying pre-worn clothes, I really like Thred Up. I’ve gotten some beautiful designer pieces in great condition! Their return policies (and process in general) are very easy.

  5. Good tips. Not only for the office. I am constantly trying to simplify everything in my life. I am going to implement some of your ideas.

  6. Fascinating. Thank you. Have you read Marie Kondo’s book on de-cluttering? I thought it would be trivial, but I loved it, despite her somewhat precious writing style. I’ve always been happiest when I’ve owned fewer things, but things I loved. In the spring, I pared back my closet significantly. I intend to pare further when I swap out my summer clothing for my winter clothing this year. The way we are headed, global-warming-wise, there will soon be no necessary distinction, alas. Recently, I read an article one of my Cal classmates had posted on LinkedIn on what to wear to an interview. It was basically jeans with a top, with an added jacket if the wearer was feeling particularly formal. The shoes were boots or flats, depending on the season. My house host’s older daughter works in marketing for a prosperous tech giant near your house. We had dinner with her recently. She came from work in jeans and ballet flats. That’s essentially how I dressed for work as a director in Silicon Valley engineering, though I sometimes dressed more formally for meetings with customers or the board. When I interviewed people for new positions, which I did a significant amount of the time, for permanent and contract positions, I was wary of anyone who arrived in a suit. We all were. It looked odd for the engineering positions I was hiring for. The Cal article I read warned against suits altogether. I’m fascinated by the shifts. My wardrobe is mostly jeans—I love cropped, high-waisted jeans—and short boots that may leave a jean/boot gap. Open-toed shoes and sandals lure me less and less. I like t-shirts or simple shapes in sweaters, with unstructured jackets. Scarves are a staple. My color palette is white, cream, gray, and black. I used to have navy and blue—I miss blue, but I haven’t added it back in—as my contrasting color, but that went away during difficult years when my wardrobe choices became distinctly Greek Widow. I had to get rid of those pieces, some of which were lovely but oversize and depressing. My paternal grandfather was a tailor, my paternal grandmother was a seamstress, weaver, embroiderer. My mom was an excellent seamstress as is my older sister. My dad and my mom both knew good clothing, fabrics, design, though neither of them wore expensive clothes when I knew them, though my mom had a few lovely pieces from those earlier years. I think after years of USGS field work and four children, the idea of the beautiful clothing they had worn when younger kind of went out of the window. After my mom died, it made me sad to look at her one vinyl purse. She did not want anything different, but I wish I could have convinced her otherwise. Do you know of Calvin Trillin and his adored late wife Alice? Trillin’s book, About Alice, moved me because he described a woman of great substance who also loved clothes. My dad understood that was possible. I’m not sure the rest of my family saw or sees that. I’m a throwback to my grandparents, who I never met, with their beautiful clothing and their Cord automobile. Apologies, I’ve drifted from your work-wardrobe subject. I’ve been thinking a lot lately about the semiotics of clothing; how to create a wardrobe that is as fixed as possible; and my desire to spend as little money as possible on clothing once I have completed my current redo. Your previous post about men’s wallets was of interest to me because I’ve always chosen men’s wallets. I like their streamlined styles better. I bought a new man’s wallet recently because the card pockets of my previous favorite had become looser and looser, and my cards would fall out if I held my wallet the wrong way up. This is not a good thing in a BART station. Another experiment I’ve undertaken in relationship to the above changes is an attempt to find American or world brands that are well-made equivalents of designer labels. Thus, my new wallet is from Bosca, which was established in the US in 1911, the year my dad was born. I also like Frank Clegg, established much more recently in 1970, but with some gorgeous designs. My coin purse, which I think is from the 1980s, is from Bosca. (I use a coin purse, rather than the clever idea you had of putting change in a zippered pocket, since I already use side pockets for my keys and my eyeglasses.) I’ve also found Kara (NYC, Sarah Law), which has a wonderful crossbody bag, the Black Large Stowaway, for ~$400. Aquatalia, has the Peyton Small Satchel for about the same price, slightly more. I love their boots and shoes as well, but they are more in the Stuart Weitzman price category, though Nordstrom’s price matches their footwear to the lowest price offered online or in another store, so there are often significant reductions. I like finding what I consider good things that aren’t necessarily the more expensive luxury brands. Surprisingly, to me at least, if one chooses carefully, Sam Edelman has some great booties for significantly low prices. I take care of my wardrobe and wish to keep everything for years, so I hope to choose carefully and then add a piece or two a season from now on. I’d like to spend as little time as is possible shopping. I do love getting up in the morning and putting on a uniform from a few good things. Thank you for giving me the inspiration to articulate this in your comments section. xo.

    1. @Katherine C. James, I think your term is exactly right – it is the semiotics of clothes that I keep sorting here. And as you point out, the way in which we play out our family background in what we put on our backs. I do like the idea of these alternative brands, and Frank Clegg’s stuff is gorgeous.

  7. I applaud your statement that there’s no such thing as 5 pieces eery woman must own. Usually it involves a tailored suit jacket, which, with my apple shaped body, usually makes me look 5 sizes larger and squishes me in all the wrong places, under the arms, around the back and through the tummy. When I see that headline in women’s mags, I just roll my eyes. I have found some beautiful but unstructured jackets, with a short waist, work best for me. I always struggle when I think I have to wear something ‘formal’ as my body shape requires nothing like the traditional shapes associated with this word, however, I get the overall look by choosing ‘formal’ colours, neat shoes and accessories that give the polished look. There is more than one way to dress a body, and that’s what shone through in your article. Thanks, a beautiful piece Lisa, so much time put in to this. Helps us all to focus and re-focus. Cyber hugs xxxx

    1. @Tracey, This, “I get the overall look by choosing ‘formal’ colours, neat shoes and accessories that give the polished look,” is a very thoughtful useful strategy for anyone who prefers unstructured but has to present a formal approach.

    1. @Donna, Only because I find them one step more complex than dress or pants, and harder to wear with flats. But I am sure it’s possible to follow this general approach if you are better at skirts than I am. For example, the skirts I did wear were always pencil silhouette – that’s how I simplified there.

      Note: Skirted suits are a whole different proposition. The reader who asked the question works in academia, so I assumed we were thinking separates.

  8. Once again, you have deconstructed my wardrobe issues. I waver between dresses and pants and between structured and flowy, resulting in a less coherent look and way too many clothes. I suspect there is a conflict between what works best with my body and the image I want to present. No clear solutions, but I know understand the problem.

    1. @DocP, I wholly understand. I think you can start with your body, and then use color, texture, accessories to get to the image you are looking for.

  9. Working in the corporate world is so different than working with special needs students…I would have loved to be able to dress up a bit more. I did wear jangly bangles as they helped my autistic students focus!

    Your advice is spot on…simplicity, form and function.

  10. I love this post-it is great,everything you have to know,highly organized as always,it resonates with me!
    This should be thaught in every school( + engineering part of office clothes :-)),because I could see a lot of young women and men struggling with corporate(or other offices) dress code.
    Marina Rinaldi is great for plus sizes (from US 10,I think)

    1. @dottoressa, Thank you – I suppose if we’re going to have dress codes, even informal ones, it would be only fair to have training for them. And I love Marisa Rinaldi.

  11. You said it and nailed it for me…”Simplification is a harsh mistress…”You have given me a mantra to see me through some (for me) difficult times in culling and disposing…THX

  12. A tech company (rhymes with Schmaypal) moved into our high end downtown Boston office building. So funny to see their employees mingled with the white shoe law and investment fund people.

  13. I think I’ve done this without thinking about it. My work wardrobe (when I’m not working from home) is a heavy jersey or ponte knee-length dress (with some detail at the waist or a faux wrap) and mid height pumps. Easy-peasy and relatively comfortable. I just wish more companies did the dresses with short sleeves for summer and long or 3/4 length for winter.

    1. I partly blame Michelle Obama and partly blame manufacturer cost cutting for the scarcity of sleeves.

  14. I think it’s a brilliant idea to start with shoes as inspiration and limit your wardrobe to only those things that truly work well with your chosen footwear. Seems like the only way to have a pared down wardrobe that functions well.

    Great column even through my work wardrobe days are over. But the concept works for retirement too.

    1. @Carolyn from Oregon, Thank you so much. Here’s a retirement example. I need some waterproof shoes if we are actually going to have rain in California. So, what pants will I wear with them? Alternatively, can I find some waterproof shoes that work with the pants I already have…

      I will say that for some people feet may not be the constraining parameter. It might be they need to start with their silhouette, for example, and work from there. But it always helps in system design to prioritize the tightest constraint:).

  15. I agree wholeheartedly with what you have set down here. It is interesting how one’s wardrobe requirements change with retirement. For me, comfort seems to trump everything else, although I still want to look like I care about fashion. I’ve pared down my wardrobe quite a bit and enjoy finding my way around the new lifestyle needs. Not ready to give up all my beautiful shoes but find I need fewer shoes than before. Looking more for quality over quantity.

  16. This is really excellent. I love to see what other people would do with a “from scratch” kind of a scenario, because it always introduces me to something I would not necessarily have thought of. Like olive shoes. OF COURSE…I love olive, and it wold never occur to me to look for olive shoes. Excellent.

  17. this is one of the most useful posts about this I have ever read! And I have read a lot! Thank you so much for this, for laying all out and giving rationales for your choices! thanks!

  18. So strange, after a year of complete retirement from a life of work, to appreciate your very useful post, yet not study it for validation that I’m dressing well enough for success. I was a pantsuit, two-inch heels, good watch, pearl studs person. I also have a drawerful of gorgeous scarves I struggle to keep from wearing me. I imagine that after I die my nieces will understand, better than I, how to wear their vintage coolness with pizzazz.

  19. Thank you Lisa! I’m behind in my blog reading so couldn’t get to this until today. Excellent advice!

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