Privilege Blog

What If Stacy And Clinton Came Back, Took Your Clothes, And Gave You $5000?

How would you put together a wardrobe on $5000? I saw that Stacy London’s on TV again. Clinton’s been back for a while.  So I thought it might be time to have a What To Wear extravaganza of our own. We don’t do shame here, so we’ll leave out the Not. My take.

Elegant capsule wardrobe


How About A Little Look At The Reasoning?

  • Necessaries. Fancy underwear is great and all, I’ve owned my fair share of fancy Swiss cotton, but at the end of the day Target is my source of choice. As I’m small/medium-busted, they can even supply my bras. I wear flannel PJ bottoms to write – why not zebra stripes?
  • Workout & Swim. Here in California, where one can easily spend successive days by the pool, we need 2 bathing suits. One bikini (Thanks to Stiletto Jungle) for the days when I love the sun, one Land’s End shaper for the days I do not love my midriff. And workout gear is non-negotiable, but I’m OK with cheap Champion from Target. I’m so proud of myself for exercising that I require no image-augmentation from my sweaty clothing.
  • Outerwear. Northern California requirements are clear – we want water resistance and room for layers underneath, we don’t need industrial-class warmth. A field jacket and a lined trench would be my bare minimum.
  • Day Clothes. 95% of the tops I wear are t-shirts from either UNIQLO or J. Crew. The key for extreme casual style is color, color, color. I wear neutrals and blues, sometimes adding a stripe of a complementary or contrasting color with a layer. And I have realized good sweatshirts now get more use than my beloved cashmere sweaters. So I just might splurge on this expensive Kenzo number. (Mater has one of his scarves…)
  • Night Out. There is absolutely no room in a $5000 wardrobe for the kinds of dresses I used to enjoy. No Prada, no Narciso, no Dries. No Lela Rose. What to do? I think I might buy a dress from Siri, in a perfect fabric, in the perfect color, and wear it so often it became my signature. I think I’d be happier with that than multiple cheaper department store dresses. For non-dress dressup, I’d stick to dark wash boot leg jeans, (happily inexpensive!) a black linen-cotton sweater from Brora,  and edgy comfortable shoes a là Une Femme and Duchesse.
  • Accessories. Those who can wear costume jewelry survive this category much better than I do. Needing precious metals, I chose a reasonably priced pair of gold and diamond hoops, and some interesting lavender pearls. The bag is Village England, a brand I learned of via That’s Not My Age. It’s logoless. Booyah! And a pretty colored cashmere beanie from Brora matches the requisite Etro scarf. Another case of picking quality and allowing it to become your signature.
  • Shoes. Turns out, we women buy a lot of shoes not because we are fetishists but because we know instinctively that shoes can make an outfit. I like comfortable modern footwear, with a little attitude. Nikes, Vince, Birkenstocks, Havaianas (lavender!). And, again, no more Louboutin, Caovilla, or Choo. To dress up, I’d go for a pair of generic satin heels, in a fun color, with a bow. Paired with the Siri dress, memorable. And I could buy new pairs of shoes in a different color for future events. At $79/each, doable.

What I Had To Give Up And A Brief Summary Analysis

Technically, Stacy and Clinton never threw away people’s underwear, jewelry, handbags or workout gear. So we could repurpose those budget amounts, stick to the concept, and augment this very sparse list. What would be the next items, or the next upgrades to items on the list? I have a few candidates. You probably have others.

  1. I’d want a casual blazer. Something to wear with jeans for polish.
  2. I’d miss my Comme des Garçons fierce heart tee, would probably replace it.
  3. In making this list, I thought I wanted this Michelle Mason $600 raincoat, but I realize that’s for my pretend, swash-buckling life. In reality, I’d go for a motorcyle jacket, leather or canvas.
  4. Since I’d be keeping my jewelry, I wouldn’t need a 3rd pair of earrings (which would have been semi-precious chandeliers) or a necklace. Or a watch.But those are very necessary parts of my wardrobe.
  5. My beloved Valentino Tangos. With this budget, one has to rely on one’s own creativity for impact – there is little room for extraordinary pieces.
  6. Rain boots. In the California drought, I forget.
  7. More tee shirts. More pajama bottoms. More shoes. Probably even more shoes.

But no new category. Once you find a happy style, (for me, Extreme Casual/Polished Tomboy,) you stick to it, no matter your budget.

And with that, I’m off for the usual Quarterly Privilege Break. See you in a week(ish), with new posts, but I look forward to your thoughts on the $5000 wardrobe and chatting with you below.


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57 Responses

  1. This is a fun and interesting exercise. I’m going to work on it this weekend! Have a good break.

    1. @Susan, If you do the exercise, be not surprised if it’s hard:). This post took me DAYS. I’d love to hear your thoughts, if you feel like sharing.

    2. I will skip the underwear and workout clothes and stick to the other items–thinking $5,000 will be stretched thin.

  2. I love that you, too, feel proud of yourself for exercising that you don’t need the “image-augmentation” of fancy workout gear. I feel exactly the same way.
    I’m already wondering what my retirement wardrobe will look like — suspect that ours will have much in common (I have the Birks, the Vince — mine are moccasins, not sneakers, but close — the boyfriend jeans, etc., etc)

  3. Back to say Thanks for the link — didn’t spot it earlier! LOVE that Kenzo sweatshirt! I think I’m going to keep wearing my cashmere in retirement, but I’ve been expanding the sweatshirt options as well and that one could easily justify its price. Gorgeous!

    1. @Frances/Materfamilias, The link wasn’t there until I read your post this morning and added it;). I can see in your more northern climate cashmere would stay in rotation. I can also see how you would be proud of your exercise – damn girl, a marathon?!?!?!?!

  4. I am with you in the inexpensive workout gear too….I buy mine from Lands End when they have a sale or Costco which is a, great source for workout wear. Target is closing here in Canada and I bought a couple of pretty lacy bras…will miss them.
    $5000 actually does not go very far when starting a wardrobe from scratch and one would think it should!

  5. In my retirement my clothes are relatively similar to yours(and probably a whole lot of your other readers). Mainly,we want to be comfortable in our day to day life, without resorting to what you call the “schlump”.

    Glad I’m not the only one who thinks Target is a lingerie store.

    Your quest here was great, but way too much effort for me to attempt.

  6. In my retirement my clothes are relatively similar to yours(and probably a whole lot of your other readers). Mainly,we want to be comfortable in our day to day life, without resorting to what you call the “schlump”.

    Glad I’m not the only one who thinks Target is a lingerie store.

    Your quest here was great, but way too much effort for me to attempt.

    Hope you enjoy your break, any travel plans?

    1. @Mary Anne, It was SO MUCH WORK;). Seriously, sticking to a rigorous budget without compromising style commitments is way tougher than I knew. And no, no travel, just enjoying the beautiful weather here and trying to forget that we need rain so much.

  7. Stacy and Clinton let people keep wardrobe items that worked and were in good repair. $5000 goes a lot further when augmenting a wardrobe or transitioning to a different lifestyle than it does if one is truly starting from scratch. They posted on their website the breakdown of how the money was spent. About 10% usually went to alterations/tailoring. A good lesson for those of us who aren’t a perfect fit model.

    1. Ah, see I did no research beyond all those episodes I watched:). Had no idea they had a website, or further analysis, but that makes total sense. And I didn’t include alterations in the budget but clearly I should have. Also, the money for shoe soleing, which I always have done.

  8. Oh, I like this post. So far this week we’ve had two days of sun and 80 degree temps and two days in the 40s, one overcast and one heavy rain, so my clothes and what’s good-looking and appropriate are on my mind. I’m hoping to spend part of the day Saturday editing my closet, so this post is a resource I’ll consult again. And thanks for the link to Village England, which is new to me, but I took a quick peek and can’t wait to return. I’m a big fan of no logos!

  9. This is a very interesting exercise, and one that got me thinking about my excesses. Would it be possible to pare things down to only those items that I truly love, and jettison the rest? Could I get by with one Barbour wax jacket, instead of the 6 that I own? Would 6 pair of footwear be enough (clogs, Birkenstock Gizehs, Bean Boots, wellies, running shoes, and a decent pair of loafers)? Would 2 sweaters do me (one heavy wool cable, and one cotton crew neck)? Did I really need that $700 parka that I splurged on this winter? Yes – no regrets with that one here in NYC. And on and on. A quick back-of-the-envelope calculation puts my replacement list at $4,364 so far, and I realize I need to exercise care with my remaining choices. Thinking about this made me wish I could go back and not buy a lot of the stuff I’ve accumulated over the years.

    1. @Sheila, In doing this, I realized that whether or not I actually pared back the wardrobe, understanding what I really wore, and where I wanted to splurge and where I could buy very cheap, was useful. I try not to regret anything, but surely a part of retirement saving should have been self-awareness about the role of luxury spending – in my case at least.

      It’s also true that the more I know about

  10. I cannot recommend Everlane highly enough–both t-shirts and sweatshirts–for being both the softest cotton tops I have ever encountered, and also great values. And because they’re made of “real” cotton, they only get softer with more washings.

    1. I have two Everlane cashmere v neck sweaters. They are quite nice. I am supposedly over their size limit, but their size large fits me well.

  11. I’ve never heard of this TV show? But for this exercise of $5,000 I’d buy a good pair of medium wash jeans, a few white and gray tee shirts, a field jacket, a pair of gray skater shoes, and a very expensive handbag.

    Enjoy your blogger break.

    1. @kathy, I agree with you. A very expensive handbag such as a Celine bag for about $4000? That would be all you’d need with your jeans, t-shirts and field jacket :-)

    2. @kathy, ;). You’d be so stylish. I love the thought. And What Not To Wear was a show where 2 stylists dressed people deemed to be in need due to their poor wardrobe choices…

  12. What a great post! I always loved Stacey and Clinton on WNTW; Stacey’s new show is not nearly as much fun. Phew…can’t imagine letting S and C toss my wardrobe. I get all clutchy just thinking about it. And as for rebuilding with $5000.00…I don’t know if I could do it. I’m going to have to go and think about this. On the other hand, reading all the comments makes me wish that we could all gather at your house, sit around your kitchen table with numerous bottles of wine and discuss this further:)

  13. such a great post. how fun to start from scratch! and buy a uniform that you’d wear over and over again. Much like the French do it – great basics and a dash of style. I wish, so much, that I could ditch my marginal wardrobe and take such a considered approach. Not today but maybe soon. again, thanks for posting – lots of fun!

    1. @Jill, My pleasure – it is a hard exercise. And I did think, as I finally figured out what I could fit in the budget, how French it seemed.

  14. I LOVE this! I’d spend 4K on lingerie and 1K on cashmere :-)

    FWIW, my daughter’s friend’s mother (I know, hard to figure out) went on WNTW Canada. She’s very chic but she wanted 5K worth of new clothing so she got her friend’s to nominate her. (BTW, heard this from the kid, not the mother.)

    1. @K-Line, Hahahahahaha. You’d have quite the fan club, I imagine. I can’t imagine the chutzpah required to fake WNTW out.

  15. I’d never seen them take away anyone’s jewelry. You already have some nice jewelry so you could deduct that from your exercise total and splurge on something else.

    I’ve been looking for a utility jacket in green or blue and haven’t had any success. I guess if I were willing to pay $$$ I’d have no problem (look at Barney’s website for a good laugh). I have a thrifted Eddie Bauer one that is OK.

    BTW, my Patagonia Vosque 3-in-1 was just OK in Anatolia this winter as long as I layered with everything else I brought along. I knew it would be cold, but I didn’t realize just how cold it would feel due to the high humidity.

    1. @AK, Yes, totally, I’d repurpose that part of the budget. Frankly, I should probably have some of my cheesy 80s stuff remade:). Anatolia! What an incredible adventure.

  16. So glad Stacy and Clinton are back – certainly missed them. Although, I never much enjoyed the “throwing out of the old”, which was sometimes emotionally brutal.
    Your selections are totally you in your new relaxed life! The nice thing about inexpensive workout clothing is you can replace them so easily.
    A friend of mine has a navy dress she says she wears so often to luncheons, it can attend by itself!
    Enjoy your much time away! xo

  17. Love this topic!! I just recently purged my entire wardrobe and kept a small core of the things I love. ALSO now working with a very limited color palette, as I have let my hair be its lovely natural gray and my colors now are different. Blue jean based for sure, living is simple now. I also like quality jewelry , earrings mainly and have only 2 pair. I look forward to building a small wardrobe. Too much is like a hindrance!!

    1. Too much unworn just reminds you of those things you thought you were going to do, or ways you were going to look, that never happened. Those things unworn with good memories, I keep:).

  18. I’d happily follow your picks (but would have to ramp up the warmth of the outerwear and tops). But why not shop the resale market (boutique or online) for a good bag and scarves?

    And I’d check back often for those “add ons” like the good blazer, trousers, even shoes? Even thrifts can supply treasures; I just saw a luscious caramel MaxMara coat in one, missing a button but so easy to fix- for $35!

    1. I’ve never gotten comfortable with thrifting. However, if you click through the links, you’ll see that some of these pieces are on sale, the field jacket from Steven Alan, etc. What I would do is hold onto this graphic, and then shop strategically, waiting for sales.

  19. I really like this exercise and think it would be fabulously useful in terms of refining one’s thinking. I might just do something similar, both with and without the jewelry, necessaries etc. I can believe the process would be harder than it would seem, but also incredibly edifying. I am also intrigued, looking at your edit, of the similarities with my own, and the differences.

    1. I found it very useful. Mostly I want to say to myself – no more shoes! Buy another cloth casual jacket instead;).

  20. Hello Lisa, First read of your blog and a thought provoking post indeed…being English I don’t this TV show. It made me rethink purchases over the years and there certainly are some regrets but ebay has come to my rescue recently as a way of recycling. My initial thought was “impossible!” but at a push and if I could keep my jewellery/watches it could be done, if the sales were on, mixing some vintage and secondhand, especially a good handbag, silk scarves etc. A great jacket plus one in leather and camel coat are a must for me, and silk shirts, cashmere…oh lord the budget’s blown already! It would focus the mind on what I really wear and need daily, probably producing a much more succinct edit of what I own already.

    1. Very nice to meet you! The show here was based on a British show with Trinny and Susannah. I came away from this exercised heartened – I feel that I could pretty happily exist on less if I needed to. It also helped me refine, as you say, exactly what I do need in future purchases. I’ve been giving away my old good stuff to the American Cancer Society. For the few pieces with a relationship to the blog, I’ve been thinking of selling them here in the next couple of weeks. I find I am sentimental about beautiful and luxurious stuff.

  21. I like my clothes. I like my style. I’m plus-sized with wide feet that require special insoles. I also have balance issues. If Stacy tried to get me to wear pointy-toed shoes of any height, I’d laugh in her face. My work-out is walking so other than comfortable, supportive shoes, there is no special clothing required. I wear well-made, comfortable bras and underwear, all bought on sale. My bra requirements are unusual. I have sensory issues so I can’t wear anything that bothers my skin and I have to cut the labels out of most things. No wool of any kind, no cashmere. I try to take care of my clothes so they will last. I prefer certain brands but try to buy everything marked down at least 40%. I shop Nordstrom Rack, Ebay, too. I have a Rachel Pally White Label dress that retailed for $260 that I found for $45 on Amazon. It looks amazing on me, fits my lifestyle, and should last forever.

    Although I do perfectly fine on my own, it would be fun to have someone else do my makeup for a change. I love trying new face makeup and lipstick colors, but I can’t wear anything much around my eyes because it makes them itch. I wish I could wear it now that my eyelashes are turning white but mascara is the worst.

    No one is cutting my hair but my own hairdresser. I’d let their guy blow it out. My natural hair is fine and straight, although the white hair coming in is a little wavy. The way I have it cut now gives it shape and movement. I can let it dry naturally most days so it stays undamaged. But other than shampoo and a dab of leave-in conditioner to keep the grays from looking unkempt, I don’t use product on my hair. I dislike the way it feels.

    Everyone who goes on that show ends up fitting into a certain mold because they’re bullied into following the rules (I don’t like that show at all, can you tell?). I’m not that malleable, shall we say. Given all of this, I don’t think anyone who knows me would be foolish enough to refer me for a makeover, not that I think I need one.

    Not this week (Father just out of the hospital, Husband having minor surgery on Thursday) but when I have time, I will look around the web and see what it would cost to buy a minimalist, capsule wardrobe following *my* rules and post it on my Pinterest. It should prove enlightening.

    1. @Wendelah, I think it’s good to be centered in what you know about yourself. The only thing I try to watch out for, is saying things about myself to myself to defend myself. I try to make sure I am open to being wrong, even as I assert that I am right:). Would love it if you shared your Pinterest name here.

  22. It can’t be a coincidence that a post involving a ‘Clinton’ would have a ‘no shame’ provision. Madame Secretary would go all-in on pantsuits and I do give her high marks on style and her hair from the ‘Guernica’ press conference was indeed righteously fab.

    Lisa, I do believe you got this one right although I’d shift a few of those accessories $$$ over to a little peekaboo peignoir in the Necessaries….and hope for one of those Mae West summons of “come up and see me sometime…”

  23. I am with you that workout clothes are non-negotiable. I love that they are #2 on the list — right after underwear. You have your priorities straight! Although I work full-time in day clothes, I probably spend more hours per individual item in my favorite workout clothes than in any other other individual piece of clothing, save, perhaps my favorite pj bottoms. What fun — and food for thought too.

  24. I used to love that show, and once, when we were in a store dressing room, I had my Mom laughing until she required “Depends” with my spoof on Stacy & Clinton’s take on “mom jeans” and how big they make your butt appear. (She bought the midrise bootcuts I recommended, btw!)
    I used to think I’d answer “Yes” in a hot second, but now that I’ve developed a wardrobe of flattering clothing that I really love, I’m not so sure I could do it. Seeing how little there is for $5,000 puts me into panic mode.

  25. @Lisa. Unlike the “What Not to Wear” hosts, I don’t think there is a single right way or a wrong way to dress. They’ve created a very narrow, very conventional set of rules, and figured out how to make a living bullying others into following them. I’ve opted out of justifying my fashion choices to others. Within the limitations of budget, size, and physical disability, I dress however I like, with one exception: I keep my hair shoulder length to please my husband and he keeps his beard to please me. It’s a fair trade off.

    Although I would never allow “What Not to Wear” take away my clothes, I can foresee one circumstance that would require me to recreate my wardrobe virtually from scratch: a natural disaster, like that 8.0 earthquake that’s overdue. So far, I’ve spent a little over $2,100 of virtual cash. Since there’s no television deadline, I’m taking my time, but I probably ought to buy myself some underpants…

    My url on Pinterest:

    I love Pinterest so much.

    1. @Wendelah, Thank you for sharing! So fun to see your Pinterest board and your choices. Makes the idea itself more nuanced to me. Underpants can be useful – the going commando thing that young celebrities like to dare never really appealed;).

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