what does $95 worth of tailoring get you?

three perfect skirts and a lesson in letting go.

Happy weekend sweet peas. Some quick news:

• SF Chronicle restaurant critic MacKenzie Chung Fegan wrote this article on being asked to leave the French Laundry, and it quickly became the center of local food scene *discourse.* It reads like an A24 gourmet-horror short film…my favorite bit was the description of her disguise, which featured “extra-large, celeb-off-duty sunglasses.” So if you’ve ever wanted to know what sunglasses a food critic should wear to stay incognito at a Michelin star restaurant, Fegan told me hers are from Steven Alan. This is what they look like in a different colorway.

• I was nervous to make my first Japanese eBay order since the tariffs, but my recent order arrived smoothly and without any surprise fees. A few readers messaged me as well reporting their orders were delivered without a hitch—just keep it under $800 and you’ll probably be fine. I ordered a pair of $40 mint condition yellow Martiniano glove flats that were too good to pass up.

• Are you interested in sponsoring a Molehill event in San Francisco? Fill out this form. I’d like to bring back the fragrance swap that sold out last fall!

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In today’s newsletter, I bring you along into the tailor’s dressing room with me.

I had a pile of summer clothes (mostly skirts, let’s be real) that needed some alterations. So I stuffed them into a frayed Monterey Market grocery tote bag and brought them to my tailor, Thanh, who I trust with my most precious vintage pieces because she made my Uptown Girls birthday dress dream a reality.

Tailoring comes up a lot in the Substack fashion discussions, especially in the chats. Whenever someone chimes in with a fit conundrum, a helpful reader or two will offer advice, often recommending a trip to the tailor.

I think this is wonderful: tailoring is a skill that should be valued more in our society, and it unlocks major potential in your closet. However. I find that “tailoring” is often thrown around as a panacea for all our fit concerns (I am guilty of doing this too), as if it could magically fix every single little thing we find unsatisfactory about a $50 dress we ordered off eBay. When we talk about tailors as if they were fairy godmothers with wands (yes, sometimes they can pull off the seemingly impossible!), we run the risk of placing their profession on an idealized pedestal.

This can lead to unrealistic expectations of what a tailor can and cannot do.

This also skims over the very real experience of awkwardness or anxiety around body image/dysphoria that can be arise when someone is perceiving the size of your body relative to a piece of clothing!!! Getting clothes tailored is not always easy. In fact, it’s emotionally exhausting at times…even if you know it’s something you want to get done.

I am lucky to have developed a warm, trusting relationship with my tailor. I can tell she loves beautiful clothes, and wants her clients to feel the most beautiful girl in the room. But it was a process getting here. I spent months bringing low-stakes alteration jobs (pants hemming lol) to various local Bay Area shops until I found her. It’s like finding a therapist or dentist…you should try a few and figure out what makes someone the best fit for your needs.

So here’s to sharing realistic stories about tailoring, in all its highs and lows.

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I brought a total of three skirts and one dress to the tailor. These were the fit problems, my ask, and the end result for each item.

My total bill was $95, which takes into account that every skirt I brought in was double-lined, and thus extra labor to tailor, as opposed to unlined skirts.

Item: Vivienne Tam Dark Floral Mesh Skirt

Fit Problem: Too loose in width, and too long. I ordered this on Poshmark and the tag says “2” but that doesn’t mean very much because Vivienne Tam mesh is something of a miracle material that can shrink and expand by enormous margins.

It is the stretchiest mesh I have ever come across, and I personally think it looks best when it pulls a wee bit across the hips to reveal a whisper of the butt shelf from the rearview. But there’s too much fabric here for me to achieve that effect, and it drags on the floor. Also, the waistband was totally stretched out from age, so the skirt would sag down my hips when I walked.

My Ask: Trim the excess length, take in the sides, and get the waistband functional again so there is more “hold” around the waist. My tailor said she could replace the interior elastic with a new one, but that it would be a thicker band, and I thought about it for a second and decided I didn’t like the idea of that. My imagination went to images of 2010s American Apparel skirts with the thick cummerbund waistbands and bumpy ruching…it just seemed aesthetically risky so we decided on sewing in a nifty little clasp system. It has notches placed one inch apart.

The Result:

My tailor said out of all the pieces I brought in, this one was her favorite. The length is great, but the notch system was not actually as useful as I expected. It didn’t hold well because of the way the mesh falls on the body and kept getting un-clipped. Ultimately, I realized I should have just used a brooch to clasp it all along, it’s more secure and I like how it looks. In hindsight, I would have skipped the waist alteration and saved some $.

old prada sunglasses / bikini top / green silk slip / MNZ wedge / silver brooch

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Item: Vivienne Tam Patchwork Mesh Skirt (another one, yes)

Fit Problem: Similar as above—this one ran smaller than the dark floral one around the hips and waist, but it was still too long. I had been wearing this skirt with tall boots to mitigate the sensation of puddling fabric around my feet, but it wasn’t comfortable. And with summer here I plan to wear this with all kinds of flat sandals and bare strappy heels, so yeah—the extra length needed to go.

My Ask: Trim the excess length, take in the sides a smidge. I always find it amusingly awkward when I try on pieces and walk out into the “big mirror” for the tailor to see. How quickly I feel the need to seek her approval….sometimes I feel embarrassed when I gather the fabric around the hips, pull it taut against my butt, and say “I want this to look a lot tighter!”

This is probably due to the inevitable fact that she is an older Asian woman, and even though she has done nothing to make me feel judged at all, the sensation of her eyes perceiving me brings me STRAIGHT to being 13 and coming out of the Hollister fitting room in a cami and miniskirt to see my mother’s restrained frown of disapproval. All I can do is laugh and try to stand still like a mannequin as I get pinned and measured.

The Result: A small tweak made a big difference! Fabric is less lumpy, and hits around my ankles.

old prada sunglasses / bean necklace / ozma silk scarf / red leather pouch / prada platforms

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Item: Moschino Cheap & Chic Doll Skirt (a version of this piece is famously worn in Uptown Girls, one of my top fashion movies of all time).

Fit Problem: God, I want it to be a true miniskirt sooooo bad. But because of the size of the appliques, I can’t just hack off 1/3 of the skirt unless I’m ok with beheading three cutie little dolls. How much length can I take off the top without it looking botched?

My Ask: Cut as much as fabric off the top as you can without getting TOO close to the doll heads. The answer turned out to be 1 inch.

The Result: It’s really subtle, but I notice the difference and that is what matters. I still wish it were shorter, but ultimately with elaborate vintage pieces like this we can’t have it all. It would be criminal to cut off the doll heads or legs. Thanh told me the handiwork on the dolls was very impressive, and that they simply do not make clothes like this anymore. It’s true!!!!!

old prada sunglasses / old t shirt / old prada kitten heels / old miu miu bag

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Item: Vintage Silk Floral Dress. I saw this on eBay and was immediately smitten with the pale blue, the delicate daisy print, and I could tell it would have a gorgeous bias cut shape. I’m a hoe for 100% silk I bought it for $50. I figured that it was worth the risk because the measurements seemed about right, and tailoring could solve the margin of error.

Fit Problem: Hah, I was soooo wrong. It fit perfectly from the bust down, but too tight in the armpit/shoulder/lat area. I really wanted this dress to work out.

My Ask: I assumed I could just ask to have the armpit hole enlarged, taken down lower, and make the straps thinner so the back felt more open. Thanh let me finish my rambling, and said in a serious tone—”if you want my honest opinion, don’t spend any more money or work on the dress.”

I was in denial at this point. “Are you sure? Well, what if you just cut it deeper here, or reconstruct the neckline….” I trailed off, stared at my reflection and felt my cheeks grow hot.

She explained that sure, she could technically do what I was asking, but that it would severely distort the way the fabric would sit across my chest; it probably wouldn’t feel comfortable. This was the first time she had ever told me no when it came to an alterations project.

I knew she was right. I just didn’t want to hear it.

But we had built enough trust over time that I knew she was speaking with my best interests in mind, so I retreated back into the dressing room to wiggle out of the dress, straining to pull it over the bottleneck of my shoulders. Was this what it felt like to get honest but critical feedback from Tim Gunn on Project Runway??

I tried not to let my disappointment show, but as I bagged up my clothes and prepared to leave, Thanh kept reassuring me that trying to tailor the blue silk dress wasn’t “worth it.” I nodded, knowing that I’d have to emotionally let go—but in this moment, I wasn’t ready. It would take time.

The Result: It took me 2 weeks to come to peace with the fact that the dress did not fit, and it was a disservice to my closet and my mental health to hang onto it. I decided to mail it to my sister—a wonderful fate for the dress, the second best outcome I could hope for.

Before I packed it in the USPS box, a little voice in my head whispered “just try it on once last time. Maybe it will magically fit.”

I held it up against my body in the full length mirror. It was a beautiful dress.

But I no longer saw myself as the person who was meant to wear it.

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xoxo viv

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Thanks for being here. You can find me on IG and TT. My wardrobe pieces and recs are saved here—unless it’s vintage, of course ;)

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