What would Peggy Olson wear in her '40s?

May 22, 2015 8:55 AM

I am a mid-thirties woman whose professional style is currently somewhat girlish (think this, this, this, this). As I move into my '40s, are there looks that keep this "feel" but in more age-appropriate ways?

I've never been especially fashionable, but to the extent that I have a personal style, it's fitted somewhere between Princess Kate, Allison Brie in Community, and Mad Men's Peggy-- ladylike, demure, classic, and a bit fussy/schoolgirly. Lots of sweaters with full above-the-knee skirts, shortish fit-and-flare-style dresses, jumpers with blouses, trousers with scarves and little vests, etc.

This is partly a matter of taste, and partly what I've got to work with: I'm shorter, slightly built and straight-shaped, with a thick, short waist and small bust but nice legs, so I work "girlish" far more easily than "womanly" or "dramatic". Cheerful, nondescript, cuteish-at-at-best facial features. Personality-wise, I tend to default to a friendly, ingratiating, but somewhat uptight/ formal/ slightly-awkward presentation style (again, a la Allison Brie in Community), so either hip, earthy or high-impact looks are hard to pull off.

My concern is that this seems like a persona that works best in someone young(er). The fussy little collars, puffed-sleeve blouses, short flared skirts, Mary Jane shoes, etc., all pretty clearly go to a cute-feminine vs. a cougar-feminine place, and in the absence of cute, "ladylike" seems like it'd shade pretty quickly into "dowdy" or "secretary." As the years roll by and I have to phase out some of the inappropriately youthful elements of this look, I wonder where this personal vibe can evolve in its '40s and '50s. Thus, Metafilter, I'm wondering:

(a) At what age do looks like these start to read as pathetic or mutton-dressed-as-lamb?

(b) At that point, is there a midlife cousin of this style that I can adopt, keeping the classic femininity, prissiness and boy-body-friendliness but without the requirement for youthful cute? Either direct suggestions or style role models would be most welcome, and I'm happy to keep going back to the vintage well if that's the best place to find something like this. Thanks!

posted by Bardolph to Clothing, Beauty, & Fashion (12 answers total)

Check out Shabby Apple and Boden, especially the " wear to work" lines.
posted by veery at 9:11 AM on May 22, 2015 [1 favorite]

Swapping the flared skirts for pencil skirts will get you most of the way there, even if you change nothing else.
posted by Metroid Baby at 9:46 AM on May 22, 2015 [6 favorites]

I think you should check out all the "mature" lines, because most of them have outlier pieces - I have a modest amount of Eileen Fisher, for example, because their fall/winter lines tend to have a few interesting, shaped pieces in good fabrics.

Everything there is summer right now, so "loud and godawful" describes a lot of it, but Talbots tends to have occasional adult yet charming pieces like (to my mind, anyway) this contrast swiss-dot blouse. Talbots tends to have about 1/2 very blah button-fronts and 1/2 very early-seventies structured-mod stuff, especially in fall/winter.

I was just noticing a woman who had entirely grey hair and was probably in her late fifties - she was wearing a rather nineties floaty knee-length skirt and had a cute little bob with very short bangs. What I noticed about her look was not that it was too "cute" but that her clothes didn't fit quite right - the skirt was a little too long, as was her jacket. It seemed to me that since she was petite, she was probably having trouble getting pieces that really fit per proportions. The outfit on the whole was charming, but it looked a little off because of the proportions.

I think that if you keep a lot of the "cute" stuff but in slightly more subdued colors/patterns (and no tight vests!) and keep the fit right and keep your hair contemporary, you can continue to work a lot of those looks. Maybe make sure you have only one "cute" detail per outfit - full skirt and sleek sweater, bow blouse and classic pants.

In terms of shoes, I think directional shoes with few details are probably the best way to go - what I notice on women my own age and older is a tendency to rather blah shoes from five years ago. Also, nothing puffy unless you're wearing trainers. Puffy leather shoes with "fun" details don't look good on anyone - ie, no Clarks. Everlane has been making some sleek flats that look good to me. Also Repetto makes a nice ballet flat.

(Could you not use "secretary" as a pejorative implying ugly, inferior, badly-dressed, etc? Some of us are secretaries - and when you're working class, a secretary gig with benefits is a good gig.)

(I assume that you make more than I do based on the secretary comment - so I have no qualms about the cost on these. I tend to get my stuff used.)
posted by Frowner at 9:47 AM on May 22, 2015 [8 favorites]

I think it's easier to keep more girly/cute elements in your wardrobe if you make a real effort at being perfectly groomed (i.e. eyebrows, makeup, jewelry, nails, etc.) and the clothes themselves are very good quality and don't feel like fast fashion. However, if you want my honest opinion, I would probably ditch puffed sleeves, fitted sweater vests, Peter Pan collars, and girlish Mary Janes over the next few years. (I'm a little older than you and have not felt comfortable with any of that since my 20s, but that's me, not you.)

How do you feel about taking this in a sort of Junior League direction? It requires some simplifying compared to your current style but seems like a reasonable "grown up" next step. You could do a lot of cardigans, sheath dresses, shirtdresses with full skirts. A sort of grown-up 50s lady vibe.
posted by chocotaco at 10:21 AM on May 22, 2015 [2 favorites]

A full skirt that hits at knee-length or lower reads more grown-up and classy than a short one. I think the second dress you posted (the houndstooth), as well as anything that Kate wears, would look good on a woman of any age.
posted by noxperpetua at 10:32 AM on May 22, 2015 [1 favorite]

Response by poster: (Sorry about that "secretary" line, Frowner-- all the people I've known who sit at those desks nowadays have been "admins" with greatly expanded responsibilities (and for the most part beautifully dressed, I should add), so I meant to refer to the dowdy 60s-70s maiden typist archetype, not to anyone who now works any analogous job. I will, in any case, avoid references like that in the future.)
posted by Bardolph at 10:41 AM on May 22, 2015 [5 favorites]

How about keeping the general shapes but going for simpler silhouettes? A solid colored fit-and-flare dress is feminine and timeless; go for knits, e.g. ponte, if you don't have a defined waist. Same goes for skirts: wear a full skirt that hits at your knee or very slightly higher (but not lower if you want to avoid navigating possible frumpiness), and avoid frills but add interest through color or pattern. Pair with a simple top like J.Crew's Tippi sweater (or a peplum style works well to create the illusion of a smaller waist). Materials like lace and sheer overlays read feminine without being girlish.

Alternatively, keep a few of the girly details that you love but on classic/conservative silhouettes. For instance, puffed sleeves on a plain and unembellished blouse worn with trousers could work. You don't have to say goodbye to Peter Pan collars forever, but make them the only "young-girl" element in your outfit.

I second the recommendation of looking to Boden for pieces to purchase. Anthropologie might have been a good style inspiration in the past, but recently it's gone off the boho/trendy deep end. If you like the Junior League direction suggested above, here are some fit tips for a straight figure (I have a very similar body type):

- sheath dresses will usually fit better than a pencil skirt + tucked top

- don't be afraid to buy a dress one size up to fit your waist and get both the bust and hips tailored (more than 1 size up and the tailoring gets trickier)

- I think the full-skirted shirtdress is a great look for you, but personally I've found it hard to fit since vintage/vintage-inspired shirtdresses are often cut for a small waist; if you like trapeze/swing styles, the Anthro Tillie Shirtdress is awesome for a small bust/thick waist/nice legs kind of figure

- try eShakti for vintage styling and custom-to-measurements sizing
posted by serelliya at 11:14 AM on May 22, 2015 [1 favorite]

I am also in my mid-thirties and dress in a similar style to yours (although I am taller and pear shaped, FWIW). I find that Modcloth (sorry, can't ever manage to do links correctly) has some great dresses that aren't totally cutesy (although obviously they also have cutesy). For instance, the Day After Day dress is feminine and "classic" looking, but if you get one of the more sedate prints, I think it would be perfectly reasonable as you age (I hope anyway, since I love those dresses and plan to keep wearing them). Also, Anthropologie has been skewing away from the kind of styles I like, but still has some decent dresses and skirts.

As for general style, I find as I get older that the shape matters less than things like length, print, and details. I no longer feel comfortable in mary janes, but will wear regular flats. I like things closer to knee length than mid-thigh. I like simpler prints or solids. Part of it is just comfort level, but I agree with others that fit matters most.
posted by odayoday at 11:15 AM on May 22, 2015

I am also comfortable on the more serious side of the spectrum. Recently for the first time ever (I'm 31) I felt it was the right time for me to ditch my usual work clothes shop (Express) and ended up going to Talbot's (this is their "work shop"). I was pleasantly surprised. Their stuff is feminine enough without being "girly", and the quality of the clothes is actually pretty good. Their clearance section had gorgeous skirts that were made of luxurious fabrics in a way that all the luxuries of the design were very subtle. I can't seem to find those skirts online, probably because they were more appropriate for winter.

I also went to Jane Bryant, Ann Taylor, Coldwater creek and at least to me the clothes there seemed quite bland and a little too frumpy.
posted by Tarumba at 11:59 AM on May 22, 2015

You could do a lot of cardigans, sheath dresses, shirtdresses with full skirts.

Sounds like Michelle Obama. Some of her outfits have come from Talbots, including the gray and black wool cape-like jacket and the turquoise and print combo two-piece dress she wore (not together!) a few years back. (Both of these often on eBay.)
posted by jgirl at 12:12 PM on May 22, 2015 [1 favorite]

My boss, in her fifties, is also petite with a boyish figure and she rocks the Mod look. So shift dresses, ballet flats or knee boots, A-line or pencil skirts, cropped trousers, lots of little twinsets and cardigans and Chanel-style jackets. Mostly designer or high-end High Street (Hobbs, Jaegar, Browns). Very simple lines, expensive accessories, interesting or quirky accent colours and jewellery.

Very cute, very stylish, definitely age-appropriate and authoritative. She gets a lot of compliments (from other women, not sleazy compliments from men).
posted by tinkletown at 1:23 PM on May 22, 2015 [1 favorite]

I agree, Talbots is kind of a surprising secret for decent-quality, decent-looking well-made work clothes. I have also had good luck being selective with Lands End. From both these places I've found sheath dresses with interesting colors/patterns that pair well with a tailored jacket or cardigan - my uniform these days.
posted by Miko at 7:32 PM on May 22, 2015