Eileen exorcises her wardrobe demons [pt 2]

Previously, I interviewed Ms Eileen about her decision to start rebuilding her closet from near-scratch due to life and body changes—and her trust that my BTDT self could be of use as she shopped and evaluated. After sharing how we came up with a baseline color palette for her to use, I also provided detail shots of clothing that she felt communicated her three primary style loves: opulent, rugged, and boho.

Before Eileen and I headed off to shop, I had her do a little homework. She’d already identified herself as a high-hipped Hourglass (8 shape) and read up on proportions that should work well. But that wasn’t enough: before we stepped foot into spaces designed to suck money from her pockets and/or overwhelm as many senses as they could, I needed her to be calmish and clearish on her innate style preferences.

What better method to help her get to the heart of things that that of my eye doctor?

After wandering the internet, I sent her photo sets of gorgeous fuller-figured models and bloggers—chosen to offset her concerns that a 5’5 size 12-14 frame was particularly limiting—and had her choose between 1…or 2. “Bold print or subtle?” “Fitted or unstructured?” “Detailed or streamlined?” “Heavily accessorized or minimalist?” “Color-color or neutral?” “Drape-y or structured?”

Of course she wasn’t ALWAYS choosing one direction over another, but patterns and percentages emerged—mostly that with a bit of this, or when X then Y. And once we got shopping, she found her likes and dislikes of items or pairings were usually in line with her earlier picks.

Q: Here’s what I observed from your homework exercise and shopping with you:

“Whether you’re exploring your love of opulence, ruggedness, or boho two undercurrents are constant:

  • When you choose lots of detailing or print, you like to keep the overall shape relatively simple
  • You like to mix highly practical items with luxurious-feeling, often-natural fabric and/or pieces with ‘special’ detailing

“Agree? Disagree?”

A: “Agree! And if you make me sum things up more I’d say I go for refined practicality (with a leaning towards the sumptuous).”


Clearly this newfound level of confidence deserved a little attention. So on a chilly overcast Saturday my friend Arinna, past Eileen client, current covet-er of Eileen’s new clothes, volunteered to be on the other side of the “beauty maker” reflector. I handled the camera and coached our model on posing.

[As I only have one pose, she quickly overtook me.]

Eileen goes from photographer to star of the show in a lush, colorful print top that ties at the waist plus a textured cardigan

Eileen pairs dark wash skinny jeans, a mildly heeled black bootie, and a textured black cardigan with a lush and colorful silk print top

Q: You say you hate to shop and you dressed in a fairly nondescript way for years. Yet your first two days of shopping you choose a lot of “icing” pieces—very memorable, high-drama items. And what wasn’t icing was quite “cake-y”—detailed, luxurious.

“I had to armtwist you to look at basics when I thought it would be the other way around!”

A: “I think I was more ready to change than I realized. More ready to stand out.

“And I do hate to shop. That’s mainly because most of the things I like don’t fit me. I was the same when I was 17 and quite literally a walking skeleton.

“I should add that I grew up in house full of women who were geniuses with fabric, patterns and sewing machines. They made clothing to fit. So, I naturally have higher expectations of clothing options.

“Fortunately, it seems that bigger sizes are more readily available these days. There could be more, but it’s better. I admit starting off with shoe and bra shopping was a good choice.”

Q: “Things looked brighter after you were in the proper size, right?”

A: “Yes. I carry weight in my stomach, and with the right bra size I had much more of a waist. Just like all the style shows tell you!”

Vintage-inspired jacket with leather trim plus a knit pencil skirt and ready-to-kick-ass knee-high moto boots

L, Buckling the moto boots; R, Eileen teams the boots and knit pencil skirt with a lightweight wool top and deco-tastic belt

Q: “Let’s talk about body proportions and touch on your body insecurities.”

A: “Ugh.”

Q: “I don’t need the worst-day nitpicky stuff, Ms Well-Endowed Hourglass, just some quick context.”

A: “Okay. I mentioned my stomach. I like the way the patterns we found really drew attention away from that area. I am giving up boxy because when I belt or wear things that fit to me I think I look a lot better. Why did I stop that? (I am a little short-waisted for belts to be 100% ideal.)

“The bust area…sometimes I’m self-conscious. Lower necklines are flattering but tough for me. I think I got a range of necklines that feel good for now. I have to ease out of the black crewneck T shirts!”

A seamed wool knit jacket in one of Eileen's best neutrals, grey, tops a print top and dark wash jeans

Q: “I kept reminding you what I remind myself: many things can be altered or it’s the damn clothes that are wrong, not the body. Did that help?”

A: “Sometimes more, sometimes less. I still have to deal with fit issues!”

Q: “Let me switch gears a bit. EM Forster has a line about his conventional heroine and her masterful, passionate piano-playing:

‘If Miss Honeychurch ever takes to live as she plays, it will be very exciting both for us and for her.’ 

“You are super soft-spoken and self-effacing and analytical, and from your ‘before’ style people who don’t know you and your photography—aka your workmates—wouldn’t realize you had this whole bold, creative, drama-loving side. Do you realize it might not be a secret anymore?”

With a layered-sleeve sweaterdress, Eileen finds a way to do Boho Vamp

Next: Part 3 of Eileen exorcises her wardrobe demons, in which outfits and others’ reactions both feature

Eileen exorcises her wardrobe demons [pt 1]

Recently, I’ve watched my pal Ms Eileen go through a lot of changes and hit a milestone or two. She turned 40. She’s taking her personal life in a new direction. And when she’s not at work she’s generally doing something related to building up her new side business, photography.

So when she said, “I’ve been thinking it’s finally time to stop wearing what I’m wearing. Would you be up for a little shopping?” I grabbed water and power bars and got down to cheerleading.

Of course, it wasn’t all pom-pom waving. There was also “Glow or No?” color opining (with a side of closet-building-from-near-scratch advice from the Vix and Fizz BTDT archives). And many a reality-bringing buzzkill of the Do you REALLY need a cocktail dress more than boots? Will you wear that sweater dress with layered short sleeves, or will it sit in your closet because you don’t want to show your arms? variety.

Unsurprisingly to me but somewhat alarmingly for Eileen, the “little bit of shopping” turned into concentrated bouts of buying. By the time we were done, however, my previously limelight-shunning pal had a versatile group of rather attention-getting clothes she could use for her business casual-casual work, for photography jobs, and for play.


Since we’re both suckers for transformation tales, she agreed to share the broad strokes of hers.

Q: We’ve known each other 5 or so years. When we worked together you worn a lot of jeans, boxier T-shirts, and long black skirts. That’s pretty much been your uniform off the clock, too. Is there a story there?”

A: “Kind of a boring way to dress, I know. But practical. And working in a male-dominated field, I fit in better with the guys (and some gals). At the start of my career in the early 90s, I mostly wore long, tailored dresses all the time with heels and sheer hose; some of the dresses had lace and other frills!”

Q: “Hey, I give you lots of credit for at least having a toe in the color/pattern world during your 30s—beats my track record. What finally pushed you to leap into a style/wardrobe overhaul?”

A: “In addition to feeling like I’m at a new place in my life, I’ve adapted some healthier behaviors and lost some weight. Upping my activity has helped me reconnect with the ‘me’ that used to be very fit, even though it’s hard not to compare myself with how I looked when I was younger and very skinny.

“I guess it just felt like time to work my way into more form-fitting clothes again. It’s been too long! Plus, I was also bored with my ‘REI world traveler look.'”

Q: “What sides of your personality did you want to bring out through clothing/accessories? What did you want to explore?”

A: “Clothing that’s fun and practical still appeals to me. But I like a lot of different styles and wanted to mix it up a bit. I mostly wanted/want to look well put together but in a fun and life-loving way. I’d really like my clothes to express:

  • a bit of refinement
  • my love of color and texture
  • my leanings toward the exotic and frilly
  • my goth punk side (it’s there…it never really went away!)

“That sounds all over the place, so I was a little nervous when I started spending money. But I knew from your posts about your “closet evolution” that you’ve become pretty logical about shopping.”

Q: “Ha! You figured if I could learn how to do it, there was hope for you?”

A: “It sounds worse when you put it that way…but yes!”

I knew my former goth-y grrrl would never give up black. But with every non-black item needing to score high on the “Glow or No?” color test, flatter Eileen’s hourglass figure, and meet one or more of her criteria, we left scads of (fairly neatly rehung) possibilities behind. Fortunately, she came away with just what she was looking to find.


Above: Aside from Eileen’s beloved black, her new cool-toned wardrobe colors (core on left, accent on right) all scored high on the “Glow or No?” test

Even better, Eileen’s combinations let her mix and match her three main style sensibilities: opulent, rugged, and boho. Devil, meet the details….

Eileen indulges her love of the full-on feminine by taking a lush, ruffled print and topping it with a textured cardigan's subtle art nouveau vibe

Eileen's vintage-inspired jacket gets a touch of danger with leather-trimmed zippers on sleeves and pockets

Eileen embraces her boho diva side with a bold 70s silhouette (that can be worn short or long) and a braided gold leather belt

Next: Part 2 of Eileen exorcises her wardrobe demons, where some of Eileen’s new outfits are unveiled head-to-toe

The Gilded Lily goes for coffee

When one rolls with The Gilded Lily, it’s best to have lots of stamina for change. Routines? Kept to a minimum. Favorites? Revolving. Styles, events, and surroundings? The fresher the better.

At 70+, friends are about the only thing she tolerates for longer than a season—but if she smells stagnation, watch out.

Since I’m already on notice for preferring to talk versus text, I’ve been trying to step up my game. Luckily, the last time we were planning an outing I had a new extra-funky coffee place to dangle in front of her.

I arrived to find Lily in a little hot-off-the-rack H&M skirt doing what she does best: gilding.

The Gilded Lily doing what she does best: gilding

She’d tossed an outrageously feminine “sweatshirt alternative” over everything, and though I’d encouraged her to buy the topper while she was enabling ME to buy a rouched black satin tamale skirt, I’d forgotten just how much pale beach-glass blue makes Lily’s skin and eyes glow.

Given how gorgeous she looks in soft beachy shades, Lily knows it kills me to see her in brights...

Probably because she is generally trying to express her inner Paris Hilton while I am generally beseeching her to embrace her inner Michelle Pfeiffer.

Just in terms of colors, I swear!

so when she humors me you'd better believe she adds on-trend wedge shooties lest anyone think she's a powderpuff

With lots of soft shades + statement jewelry + trendy wedge “shooties,” her coffeehouse outfit made us both happy. Which no doubt means the topper’s days are numbered.

Forget Little Red: The Gilded Lily proves grandmas can rock a hood like nobody's business

I know I shouldn’t be sad when my favorite Lily pieces end up in the bottom of some bag headed for donation. But then I’m the woman who retreaded 5-year old boots—OF COURSE I’m going to have something in my eye when the topper vanishes during one of Lily’s frequent been there done that clothing purges.

[And if she gives that opal-y ring away without offering me right of first refusal….]

But that’s why I need someone like Lily in my life: to show me how to live with my head pointed forward, not cricked-neck from looking back. To demonstrate an alternative to evoking memories via the security blanket of objects. To remind me that when you travel through life focused on collecting moments instead of things, there’s always room for one more.

What to wear when your Venn Diagram fails you

For some odd reason my professional life routinely comes to a slow-to-screeching halt in the late spring and kicks up again in late summer. During the transition, most of what I do tends to be home-based. While others don crisp summer office wear and hobnob with real live adults, I’m reduced to communicating via phone or keystroke whilst (unwillingly) adorned in never-stylish cat hair and (stupidly) donning clothes that accommodate a little too much snacking.

No offense to people who think the setup sounds like heaven, but: ME NO LIKEY.

So imagine my mega-excitement when an organization recently dangled a life preserver bedazzled with chunks of money in my face. Immediately, I started assembling relevant samples and crafting a presentation and running through answers for some potential “tell me about a time when” queries.

My excitement lasted until I started trying to put together an ensemble that would strike a mellifluous note with the organization’s representatives. Because fiddledeedee, that’s when I:

  • remembered that my recurring bouts of professional seasonitis correlate to an understocked hot temps ahoy! wardrobe
  • realized that my limited number of go-to conservative pieces had (not so) mysteriously become approximately 33.865% tighter
  • recalled that my meeting would involve flying to a very warm, sartorially sharp-yet-relaxed spot for an all-day adventure


Surely after all my quasi-successful efforts in wardrobe management, I couldn’t be in a horrifying Start From Scratch situation, which usually requires a Throw Money at the Problem response?

But I was. And, unless I wanted to risk deep vein thrombosis when airborne and/or post-lunch button malfunctions, I faced both a form AND function challenge.

Clearly, vigorously attacking the former issue before I began my online and in-person shopping would streamline the time-sensitive process. All I had to do was take a look at how it might behoove someone of my age + experience + “position” + personal characteristics to dress when meeting with certain broadly-drawn types during a specific season, right?

After factoring in all the obvious variables, I arrived at the stunningly obvious diagrammatic solution below.

Strategies for First-Impression-Dressing

What to Wear When Your Venn Diagram Suggests You Abandon All Hope

Trying to dress for hoped-for success often takes me to Planet Paradoxical

Note that I didn’t say it was a USEFUL solution.

As I scrambled to assemble options that seemed appropriate—a task made ever more joyful by the fact I was, in fact, often too large for size A and too small-without-dubiously-successful-and/or-astronomically-priced alterations in size B—I resolved to stop reading the angst-inducing Corporette.

Which, given its self-described mission to be a “fashion and lifestyle blog for overachieving chicks,” I have no business reading anyway.

But read I do, since a) in many ways it’s my job to be a voyeur; b) I’m a feminist and appreciate the challenges and triumphs of women seeking lucre and power; and c) the site completely contradicts my mother’s dismissive, now-ancient statement that “No one is looking at your socks.”

However, re-reading discussions on topics like “Skirt Suits vs Pantsuits When Interviewing: Choose Wrong and You’re Doomed,” “Peeptoes in the Courtroom: Empowering or Whorish?” and “Could Feminine Detailing Be Derailing Your Success?”* was starting to give me panic attacks. Obviously I needed to chill, dude.

In the end—and after consulting with a few trusted friends who were roughly familiar with the industry, the area, or both—I went with my patent-pending approach of picking an outfit sure to horrify some and please others.

Winner, Venn Diagram Overlap contest

I hopped the train to hell…er, shinytown…by pairing sedate—and hallelujah lined [thank you for getting your act together, Ann Taylor]—black wool trousers with:

  • a dark grey/faux-sharkskin jacket with a more feminine lapel
  • a sleeveless, ruffled silk charmeuse shell in one of the oft-controversial animal prints
  • my non-subtle vintage shell ring (but hey, at least I skipped the matching bracelet!)
  • my semi-broken in, classic closed-toe and -back shoes in non-classic gleamy pewter
  • that standby of the bless-her-heart brigade: HOSE

To date I’m not quite sure how judgments of my work or appearance** shook out. I DO know that my shiny, 3.5″ pewter heels and I have advanced to the next stage of evaluation…the one where I remember that scrutinizing THEM is a key part of the equation. The stage where I can wear whatever my heart desires, as long as I make sure my nerves are clad in steel.

* Paraphrasing, but not particularly exaggerating

** Having been looking at tons of luscious fall shades lately, I admit I’m a little crushed that I had to purchase more items that will grey my anatomy.

The Gilded Lily gets a headshot

The Gilded Lily (“my dress of choice is so young that I look like a contrast of opposites…a grape and a prune”) CLAIMS it was only a coincidence that she was wearing her new feathered earrings—the ones she bought in a body-piercing parlor*—the day her company was redoing their internal headshots.

She also swears she wasn’t the first to think about using a fan “on set,” just the first to shed her self-consciousness:

Someone was talking about using a fan, but no one did. When they asked me if I wanted the fan I said YES!!!!

They said REALLY?

I said YES I am not joking I want the FAN!!!!!!!”

And what Ms Lily wants, Ms Lily gets. Though unfortunately she didn’t ask the photo team to paint the wall a more flattering color.

Obviously I can’t swear that Lily is the ONLY post-post menopausal woman who would pair below-the-shoulder feather earrings with a heavily encrusted top and a tailored blazer…

but around here she’s definitely in the minority.

And since I rarely remember to bring my camera along when we’re out and about, I’m both happy and highly amused that she has this moment immortalized—and that she let me share it! So if she’s a little more of a diva from now on, I guess I’ll learn to deal.


Especially since now I know just what to get her for her 70th.

* As I said in another post: She hasn’t mentioned if the feathers were her only purchase, and I haven’t asked.