Privilege Blog

Starting From Scratch, Or, A Whole New Wardrobe

Imagine you were tasked with purchasing an entirely new wardrobe. Fun, right?

But no. Turns out it’s daunting. Where to start, when anything is possible? As for any large undertaking, you need an anchoring principle. I suggest that you buy clothes you will fact wear. For clothes to be useful, they have to make it out the door. But sometimes I don’t feel like getting myself out the door. Hmm. So my clothes have to encourage me, to ensure that I will feel comfortable, appropriate and attractive. Over the years, helped in no small measure by the writing of this blog, I’ve developed an approach that works.

We’ll communicate in outline format, because, well, outlines help tame all life’s daunting phenomena.

A. Color and Silhouette First

Before you do anything go read Imogen Lamport’s blog Inside Out Style. She’s a style consultant. She’s even got e-books, if you want the advanced course. Here’s what she will sort out.

  1. First, what is your silhouette? Imogen classifies by shapes as letters. Are you an A? V? X? O?
  2. Second, how should you wear color?
    1. If you find all that Spring, Summer, Winter stuff too complex, as I do, just ask yourself, Blue? Or Yellow?
    2. Next understand where you sit on the vivid to muted spectrum. Pastels? Or jewel tones?
    3. Determine how much contrast you can handle in any given outfit. Shades of cream, or blue against orange?
    4. Finally, sort out whether you will wear patterns, and if so, whether you like large-figured or small, i.e. big repeating blocks or eensy.

It is much easier to face down racks of clothes with a logical framework behind your instincts. Kind of like life.

B. The Privilege[d] Secret To Wardrobe Success

No more imaginary wardrobes. No more purchases to compensate for something better addressed in other ways,i.e  fights with loved ones, feelings of deprivation, wishing for whatever. Buy for your real life, and remember that under those clothes lives your psyche. One prone perhaps to hissy fits, crises of confidence, surges of optimism, or virtuous rages. Make sure you have clothes that support you from your worst days to your best.

1. Barely making it out the door

I revert to the clothes of my tomboy girlhood. Foot comfort, blues, grays, and something to keep warm that didn’t belong to my son when he was 15

Going From 0-20mph In 2018

2. Gunning all cylinders

I’ve dedicated large portions of my time to finding low heels that don’t look too Nanny McPhee. Here’s where investing in a classic jacket – Chanel-esque or tailored hunt blazer, or loose and Helmut-Langy, depends on your shape.

From 50-60mph In 2018


3. Rocket Ship

Go for the gold. Find a piece that rocks your world, and wear the bejeezus out of it. For me that might be a dress by Dries van Noten. Add jewelry or accessories that make you blink. In my case, that means anything bigger than my fingernail. Make an impact.

C. The Specific And The Universal

Some principles are universal, some specific. Universally we can and should:

  • Spend on shoes, jackets
  • Find a good scarf for winter
  • Buy pants and tops for fit first, ease of care second, fashion impact third

Specifically, however, I live in Northern California, and work in San Francisco. Here we love our jeans because we can wear them all year round. If you’re in New England, as you already know, you are going to have to add wool trousers to the mix. As for psychic comfort, dresses make me nervous. Perhaps they calm you. Understand your constraints, and adapt.

  • Climate variations
  • What is your clothing fuffy, pants or a dress?
  • And, of course, what’s appropriate to the culture you inhabit?

D. On Beyond The Department Store

Finally, move beyond the stunned, blinking, defeated traverses of large department stores. Perhaps this has never happened to you. I bow. For the rest of us, two last research tasks complete our strategic preparation.

1. Find your designer cohort

This doesn’t mean you have to buy designers, just that studying the best will educate your eye, and help you determine what paradigms you prefer. Invest your time in reviewing the collections.  Look at S/S 2013, even though those shows happened a little while back. You will soon figure out if you like Raf Simons-style asymmetry, Oscar de la Renta effervescent ladyisms, or Miuccia Prada’s intellect. Then you look for similar pieces that cost less than two tickets to Paris.

2. Find your chain boutique of choice

We all need basics. Are you for J. Crew or Anthropologie? Talbots or Ann Taylor? Up a notch, Tory Burch or Karen Millen? If you know, a priori, which small stores are apt to carry goods you enjoy, shopping becomes infinitely more productive.

There you have it.

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59 Responses

  1. My entire wardrobe consists of separates, with the exception of one or two “special occasion” pieces that were bought, well, for special occasions. But even my “little black dress” goes well with different jackets and shoes.

    If I had to build a new wardrobe completely from scratch, it would probably look a lot like my current one.

  2. “The stunned, blinking, defeated traverses of large department stores”–what a fantastic image. They can be their own particular wasteland of Dante-esque hell, can’t they? I sometimes feel there should be a sign above the entry: “Abandon all hope, ye who enter.”

    Today I will forego said wasteland, though I am headed to DSW, where the conveyor belts of ghost feet trudge dispiritedly toward the horizon; Converse has my attention with their Marimekko-print sneakers: comfort, color, and pattern, all on offer in one. Irresistible.

  3. One’s style comfort level obviously depends in part on geographic locale and age group. I, for instance, live in New England and in my early 60’s. I know no one in my age and socio-economic group who owns a pair of jeans or ankle boots. No one.

    1. Perhaps I’m overly sensitive this morning, HHH, but didn’t I say exactly that, in my last paragraphs?

    2. Dear HHH, you know that old saying, never say never! But then I’m sure I’m not in your socio-eco group. However, I am fast approaching 60 and own many pairs of jeans, more pointy toed pumps than I should, and one pair of 3.5″ high heeled Cole Haan booties. I also wear plenty of dresses in the warmer months. I live in and love New England.

    3. I live in the intermountain west, and we’re casual here. I know dozens of women in their 60s, 70s, and 80s, and nearly every one of them wears jeans. Our socio economic group is middle and upper middle class. I’m just short of 60 and I wear jeans daily. I have short boots but they’re more of the outdoor activity type.

    4. Weighing in from the mountains of Vermont, where jeans, boots (heeled, flat and everywhere in between), leggings, etc. are staples in our wardrobes. Moving here 6 yrs. ago with a closet full of corporate clothes and a pair of jeans for weekend gardening was beyond daunting. It took me many (pre-blog reading) years to figure out “me” in a resort area. Some costly mistakes were made and resold at consingment shops, but now, at 59 yrs. young, I have created new rules that suit me. It’s a great feeling. PS – I posted your Chanel-esque jacket to my White Shirt/Blue Shirt group on Polyvore, a site that proved invaluable in figuring it all out. Yes, “itztru”…that’s me.

  4. Great advice. If I may add, the best shopping buddy is one who can tell if something fits properly and understands your objectives and style. There’s not much worse than hearing “oh, not for me but if you love it….” when you ask said buddy how something looks.

    Love that jacket in #2.

  5. This is one for the ages. Really. Not just the Polyvores (which are brilliant), but the getting to the heart of things: “No more purchases to compensate for something better addressed in other ways..”. I’m not sure I want to publicly acknowledge how long it took to cleanse the closet and the house of purchases made for that at-the-time-unrecognized reason.

    One of my favorites now, and I’m coming back to read it again.

    1. Yup. I bookmarked this one. Shopping should never compensate for anything. It should solve a need ( i.e. socks all have holes). A brilliant post!

  6. Great advice…all except the last which can be dangerous. If your shopping buddy has different taste than you she may suggest or approve of things that just don’t suit you, your silhouette, coloring, or style personality. The same can be true of salespersons on commission.
    B- is the gospel truth and fabulous advice!! Thanks.

    1. In answer to the questions about friends, I have a confession. When I said “friend,” I was thinking of my sisters. My sisters and I share taste so closely that it works, and the discussions thread through so seamlessly. But I didn’t want to say “sister,” in case you guys don’t have any. Because I’m very fortunate in mine.

  7. What a brilliant post, Lisa! Could you please consider making an educational post on how to build an essential/basic fine jewelry collection wisely? Thank you.

  8. This is such a great blog post. Barring some kind of disaster, I don’t think I’ll ever have to build a wardrobe from scratch. But I’ll be thinking about this post the next time I go shopping!

    My friends, though in every other way perfectly lovely people, absolutely hate to shop. (Some people…)

  9. You are right, boot cut jeans work very well, and a blazer and a good coat are always good investments, as are scarves.
    Living in The Netherlands I have found that corduroys and an array of turtlenecks in different colors have saved me from getting constant sore throats. I like Karen Millen, specially when they are on sale. Their clothes are always properly structured, modern, cheerful and won’t lose shape over time.
    Cashmere is ideal (being thin and warm). I own a scarf and a sweater, and I hope, I will be able to invest in more pieces over time.
    I do enjoy dresses, it’s how I feel the most comfortable, but the weather does not really allow me to wear them as often as I would like (that is, everyday). Blouses in prints and patterns are my new alternative.

  10. Given the chance to start a wardrobe from scratch, I´d choose clothes of natural fabrics,
    products made in the country they are designed in, clothes I ´d actually use in my everyday life.
    I´d be willing to pay for high quality, not quantity.
    My clothes would have to feel comfortable and please my own eye.

  11. I have loved fashion and style my entire life. My body has never been accommodating to that notion, unfortunately. Before retiring I owned a fashion boutique for women and specialized in “natural fiber clothing.” I have way to many clothes but very few labels. As I do have this unaccommodating physique I tend toward “artful clothing” that is comfortable. I purchase a lot of “Blue Fish Clothing.” I must do this online. Don’t get it confused with Blue Fish sports wear. In the summer I live in FLAX. There is nothing like linen in hot climates and this is a brand that one need not iron – it is meant to be a bit rumpled looking. It can be found all over the Internet. just enter Flax Designs into Google.

  12. Brilliant, brilliant, brilliant.

    I’ve recently had to replace a good bit of my wardrobe due to a size change, but wound up mostly replacing the same kinds of items I’ve been wearing most anyway (jeans, slim ponte knit pants, longer sweaters and cardis) rather than trying to reinvent myself. Finding that silhouette and sticking to it, that’s been the biggest contributor to my own wardrobe cohesion. Most of my mornings are in the 1 and 2 speed zones.

    1. I’m pretty sure I would just replace what I’ve got. But I spent SO MUCH time thinking about Wardrobe 2012-13:).

  13. Such good points! I am definitely an X, sunset tones and jewel tones, mostly small patterns, Brooks Brothers meets Talbots is my personal style but I do enjoy a good moto jacket. GREAT points as always Twitter Mom. I know my Sugar lip balm is always on me if I am rushing to get ready, and the “larger than a fingernail = statement jewelry” is such a good point! Chin chin.

  14. I’m in need of a major wardrobe overhaul in the next six months, one in which I admit I’m a professional and need to move up from 0-2mph to something 35mph+ on most days. I’m plus-size, too, which makes finding the right pieces just that much more difficult. Loved this post, Lisa.

  15. I may find a need for a whole new wardrobe soon. Following your lead, I just let my hair go grey, heaven help us all!

  16. If I had to start from scratch I’d buy basics in black grey and whites…
    keep it simple and separates foe sure.
    Jeans yes I think I’ll wear them forever…
    BTW HHH everyone I know wears jeans.

    It looks like you had some creative fun with this post Lisa!

    1. I think separates in black, gray and white are a great idea. I mostly dress that way now.

  17. Building a wardrobe from scratch has special meaning for me and my daughter because our house burned down in the Oakland Hills (CA) fire in 1991. And the resulting wardrobe re-build had no pre-planning involved! It had to do with buying an entire outfit to go to a business meeting three days afterwards and clothing my daughter so she could go to school. It also meant rummaging through donated clothes to find things to keep us going until we had time to think about clothes again. It took almost a year to re-build our wardrobes and our lives. We’ll do a story about this in our blog in the weeks to come.

  18. I fully favor the idea of “uniforms”, if you will. That way you are always comfortable and can add the pizzazz with accessories. Swapping out accessories is always easier than shopping for clothing that fits well. Great ideas!! Great blog!!

    1. I like uniforms also. I would rather spend my time in ways other than thinking about how I look.

  19. Oh, thank you for this, Lisa. This is so perfect, so wonderful, that I got tears in my eyes reading it. I knew you would have the “logical framework” I was missing. And the next time I head out with my new list, it will be with more of the background work done.

    And my list will have this at the top: “Make sure you have clothes that support you from your worst days to your best.”

    I’m headed out today, to get started (or re-started, after department store defeat). Wish me luck!

  20. Excellent post. Love my varied collection of ankle boots and shoe booties. Love jeans. And agree: jeans, with a classic blouse or T, simple jewelry, and a scarf can make an elegant outfit that allows one to slip in anywhere with appropriate aplomb. I need to venture forth for a new classic jacket. You have inspired me to search with wisdom. I’m generally a small, privately-owned boutique person, but sometimes it can be difficult to get a classic jacket in a boutique, so I try small designer shops or Saks in SF.

  21. Wow, I’m bowled over. Your post might be written for and about me. After retiring two years ago, this January I decided I needed a personal renovation – had my colours done, which was very very helpful, starting reading everything on Imogen Lamport’s site, starting reading several blogs and did a major closet purge. All this helped me to face the facts – my clothes/accessories buying was random and totally disorganized and I had way too much stuff for my fantasy life (artsy cousin) rather than my actual life (sturdy gal). This has all been a shock as I’m a very well organized and capable person in other areas of my life. Why didn’t I see this before? It helps explain why I hated shopping. Anyway, I’ve just started to shop from a list organized around my real life and having some success – makes shopping so much more enjoyable. A phrase used by Christine Scaman (12 Blueprints website) is helping – “Any decision made from doubt, fear, or negativity is a wrong decision.” I really like the idea of my clothes supporting me. Thank you Lisa.

    1. So, the motivator can be life phase change too, new job, children arriving, children leaving, retirement. Thank you for your story.

  22. Due to weight loss, I have actually replaced my entire wardrobe twice over in the past two years and will likely have to replace it once or twice again in the next year or two.

    Because of the transitional nature of these wardrobes and knowing that I’ll only have them a year or less before passing them on to a friend, I’ve developed a list of what I must have and I don’t vary much from it: A few pairs of trousers or crops, one or two pairs of jeans, a couple of classic blouses, some layering tees, and one or two dresses in solid colors.

    At this point, I keep things simple in solids and everything is built around black. Most of my color comes from accessories.

    Luckily, I work at home most days, so it doesn’t matter if my wardrobe is small and mostly casual.

    Later on, once I hit the weight my doctor and I have agreed on, I’ll feel more comfortable investing in a larger wardrobe.

    1. And of course, the shape change. You’re in transition. My best wishes in your project.

  23. Lisa, You have such gifts for communication I would love to replace my entire wardrobe, but I’m also up for the task of facing it in its current state. Your best comment is that we should choose based on what we will wear walking out the door. THAT is the basis on which I buy new things.

  24. Great post. I’m in the “barely making it out the door” category most of the time, but try to throw in a “rocket ship” now and then. I’m trying not to buy anything more in “gunning all cylinder” category, because I just don’t need it, and have plenty. Would love to have a few more “rocket ships” ~ a Balmain jacket, for example.
    This is a great clarification of what has been muddling around in my disorganized head. Thanks!

  25. Fantastic advice! I am sort of doing this now, as I face an international move, and have to figure out what in my wardrobe deserves room in my limited luggage. When you only have two suitcases for a year of clothes, the imaginary self goes by the wayside, and you really have to be honest about what fits, what flatters, and what is consistent with the rest of your clothes.

    I am purging a lot, and planning to buy a number of “wardrobe anchor” garments in Paris when I get there. I’ve realized there are a bunch of gaping holes in my wardrobe, like non-jeans pants in colors other than black. I no longer dress like a raven, but you wouldn’t know it to look at my closet.

  26. I like that dress a lot.

    When I think over times I’ve replaced my wardrobe -after a baby, major lifestyle shift, going off and leaving my clothes in a dryer on vacation- it’s usually been psychologically unbalancing. So I’d say you’re on track staying focused on what you’ll actually wear. It’s easier to shop a little more for something you decide you need than to un-shop something you bought that’s not getting worn.

  27. You’ve given us a wealth of essential wardrobe wisdom. Thanks. One of my favorites that is only on the east coast, but has a great website is J.McLaughlin. They supplement J. Crew and Anthro with styles that endure for years, yet can add that needed extra propulsion and zip. Their customer service is outstanding. No, I don’t work there!

  28. I love every bit of this advice. It’s not your standard list of must-have’s, it’s about looking at what you need and how to shop from a totally different, sensible perspective.

  29. Ah, finally. After over 50 years of loving fashion and shopping, but not really knowing how to put together a wardrobe that would take me from 0-110, now I have everything I need. Thank you, Lisa, for the framework, for the areas of my self that I need to understand, and for the suggestion to find the “go to” designers/stores.

    Also, the wonderful blog The Vivienne Files ( provides the next step by illustrating what such a coordinated wardrobe might look like.

    BTW, “outlines help tame all life’s daunting phenomena.” is going up on my board. :)

  30. What happened that a woman is starting from scratch? A fire? Even if she loses or gains wardrobe-changing weight, or moves to another climate, she still knows her preferences.

    Can you assuage my curiosity here? When might “from scratch” happen?

    The best department stores are like assemblages of boutiques under one roof and can have far better return policies than a boutique. Some are ghastly, but others are great.

  31. One more comment. I never shop with a friend. I do much better on my own.

    Lisa, would you explain why you advise to shop with a friend?

    1. Btw., I too shop alone. Always have. Would feel quite bothered if I had to have someone along. Also dislike the SA giving her opinion.

  32. Fabulous advice, Lisa, every point is spot on! 5 months ago started from scratch a new wardrobe for a new position. Selected mostly from blue, muted, solids. Went with navy, dark grey, light grey, and black suits. Added brown tweed, blue-red, and cobalt blue jackets, worn with “columns” – same color slacks and tops.
    Comfortable shoes took 3 months to find – went with AGL flats in black and beige. Added two lengths of pearl strands, gold and silver chains, with various faux gem stud earrings.
    Looking to add a few cashmere cardigans and lighter weight suits for the warmer months to come. Your tips are right on the money!

  33. I’ve actually had to do this. Car got broken into when moving to Seattle years ago and they cleaned me out of all my clothes. Luckily at the time I didn’t have much “good” stuff, but everything, right down to the underwear had to be replaced. I think I started with an olive cardigan, a black skirt, and a black pair of heeled loafers. So I could go to job interviews. Not exactly stunning sartorial material, but it worked. But daunting? Definitely.

  34. Great post Lisa.. I think my staple most days is a pair of jeans – then you can, as you so rightly point ou,t dress them up or down.. Love a comfy tee and a cashmere jumper – and I could not live without my ankle boots….
    Sometimes I go all out and have a ‘rocket moment’ and that’s usually where my little black lace dress comes in handy.. S x oh and p.s. LOVE that gorgeous bracelet from your previous post.

  35. Very well stated. I had to practically replace my wardrobe last spring when I moved to Tennessee as I came with nothing in terms of warm weather clothing that fit. I had mixed success, mostly because I had not yet sorted myself out after a few years of embattled change. A year later I am much more comfortable in terms of who I am and what I need. This spring will also require substantial restocking as I lost a size or two. The successful basics will simply be replaced and I am better prepared to seek out those special pieces.

  36. Thanks a bunch for this post. I’m nearly thirty and my wardrobe is still largely comprised of hand me downs and bargain bin specials. Some vestiges of my university dumpster diving days still lurk, and I stole some of my favorite shorts from my husband. I’m pretty sure I could use some gasoline and matches in my long overdue wardrobe overhaul. However following the advice in your post seems much more appropriate than arson.

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