dressy styles for a 60-something fashion-averse lady

April 4, 2014 5:56 PM

I have a relative who needs to get dressed up for her kid's wedding. She's asked me for advice, and I'm not sure where to look. Snowflakes, people, there are so many snowflakes.

So my relative has terrible self-image/body image, has lived most of her life in second hand jeans and Birkenstocks, feels strange and masquerade-y in makeup. The only time I've seen her look comfortable in her skin was a brief period when she was a bit lighter than she is now (she still talked about wanting to lose more weight). Loooong standing weirdness around food, dieting, fatness, etc. Also no real interest in fashion. BUT she wants and needs to look dressy and be comfortable at an upcoming country (well, rural-ish) wedding for her child. She's in her 60's and has a pretty narrow window of approval for clothing, especially clothing that takes her out of her aforementioned jeans & sandals comfort zone. Here's the pie-in-the-sky list of what I'm looking for to better help her find something she'll be comfortable in:

1. online retailer from whom she can order and return with minimal hassle in Canada
2. natural fibers wherever possible
3. styles that are flattering and appropriate for a 60-something lady who is of a healthy weight for her height
4. no bold graphic prints (subtle is better).
5. clothing modeled on older women would be ideal.

Gah. Anybody?

posted by lizifer to Clothing, Beauty, & Fashion (14 answers total)

Can we start with examples of what you think works for #3 before trying to hit the other criteria? Because my mother is your mother's demographic, along with a very healthy serving of "don't give a fuck" and she would wear this and this as shown as an outfit to a wedding. With lipstick because it's a wedding.

There's also this amazing dress but if she likes jeans, she probably wouldn't go there.

So my question is if she would be interested in that kind of boho style or if she wants something dressier.
posted by DarlingBri at 6:20 PM on April 4, 2014 [3 favorites]

Best answer: This sounds like a job for Flax (which I see suggested above) which has one mail-order/storefront retailer in Canada, that I can see:
RITSI
Montreal, Canada
tel: [phone]
email: [e-mail]

and some online retailers, which may or may not ship easily to Canada (I did not check each retailer!)
posted by crush-onastick at 6:22 PM on April 4, 2014 [1 favorite]

Eileen Fisher is expensive, but has some nice silk pieces. You mention her weight several times. Is she in Misses or Plus Size?
posted by Houstonian at 6:22 PM on April 4, 2014 [3 favorites]

I was just coming in here to suggest Flax.

If she is in southern Ontario, it might be worth a road trip to their "barn sale" in Ithaca NY the last week of April, where the clothes are on steep discount.
posted by LobsterMitten at 6:27 PM on April 4, 2014

J.Jill
posted by effigy at 6:36 PM on April 4, 2014 [2 favorites]

Also wanted to say, keep the Birkenstocks (or get some slightly 'nicer' leather sandles) long floral dress, white blazer over it, kind of like this.

The hat is also a nice touch! Could totally see a 60s mom wearing this outfit at a wedding.
posted by effigy at 6:55 PM on April 4, 2014

Best answer: Agree with Flax! She is their ideal demographic! Something like this would work.
posted by raisingsand at 8:14 PM on April 4, 2014

What about eShakti? The customizable options available may help her get more engaged in the clothing process.
posted by samthemander at 10:06 PM on April 4, 2014

Gudrun Sjoden - Fun comfy clothes, lots of beautiful older models wearing pretty wedding appropriate outfits with or without pants.
posted by steinwald at 5:17 AM on April 5, 2014

Diane Kennedy makes lovely, modest, classic natural fiber clothes in Canada. It's bamboo jersey and they have plus sizes. The owner is a doll and will photograph somebody of any age/size wearing the dress. She'll also answer fit questions with long emails. I am tempted to buy one of her dresses but the shipping to the US is just too much! They'd look good on people of all ages. I would say that the I Want It dress is pretty great for an older lady.
posted by sweltering at 5:22 AM on April 5, 2014

This is pretty much what the traditional Mother Of The Bride attire was made for. It's dressy, but sort of costumey, and much more about signalling one's role in this particular rite of passage than really about looking super attractive or comfortable.

That said, if she wanted to go with something more versatile, Eileen Fisher is the obvious choice assuming they ship to Canada.
posted by Sara C. at 9:25 AM on April 5, 2014

Advanced Style is a pretty famous blog full of fabulously dressed elderlies.
posted by oceanjesse at 9:36 AM on April 5, 2014

i would also say check out jessica london and woman within. it has plus size stuff. nothing amazing, but your mom isn't looking for amazing.
posted by misanthropicsarah at 10:21 AM on April 5, 2014

I'm guessing that because she wears Birkenstocks, she'd be comfortable in danskos. What about danskos, opaque tights, and some kind of flowy Eileen Fischer or J.jill dress that falls at or above the knee? This is what my mom wears to weddings and I think it is pretty flattering. It shows of her legs without baring too much and the length doesn't make her look frumpy. I would AVOID those mid length dresses that hit between the knee and ankles, they can look not great.
Here are some options:
if it's winter
if she has a smallish bust

posted by pintapicasso at 3:50 PM on April 5, 2014