Need to Sharpen My Casual Look
May 12, 2018 5:06 PM   Subscribe

I'm a 40-ish lady and look great when I'm dressed in business attire, but my casual clothes don't look sharp or stylish or quality. What under-$125 pieces will trick the eye enough to convey I'm classy or something?

For un-trashy weekend activities (coffee shop, brunch w the dudes), I'd love to have comfortable (stretchy, elastic, soft) casual clothes (sweat pants-type stuff l can wear with tennis shoes).
Recommendations for all types of clothes welcome: jackets, shirts, pants, shoes, eyeglasses -- as long as they're not "stiff" and uncomfortable.

BTW - I don't look stellar in black, so I avoid it.

Thanks for your help! :D
posted by alice_curiouse to Clothing, Beauty, & Fashion (27 answers total) 76 users marked this as a favorite
This is an interesting question and I'm looking forward to other answers.

My take on this is that sharp or stylish or quality and sweat pants-type stuff l can wear with tennis shoes are a hard match. I'm not sure if "tennis shoes" means fashion sneakers like Converse or old-school Adidas or if it means more like trainers/running shoes.

If it is the latter, the way I see a lot of women our age square this circle is by wearing nice workout clothes as casual clothes - lululemon or Athleta or similar. You can stay under $125 per piece with this strategy.

If you want something that isn't workout wear, Eileen Fisher is a go to for soft, flowy clothes for Women of a Certain Age. They will tend to be a little more expensive, but you could look at sales. Something else you might look at is Lands End. They have a lot of pants that are soft and stretchy but still try to look like pants.
posted by jeoc at 5:28 PM on May 12 [2 favorites]

Depending on your style, J. Jill is an option.
posted by MexicanYenta at 5:38 PM on May 12 [4 favorites]

Ureshii is colorful and soft, stretchy, comfy. Good quality and made to measure. Betabrand also does stretchy and comfy, but usually with a little more structure to the cuts than Ureshii, so it falls on the sharper end of casual. I find Betabrand fit is weird on most things though.
posted by crush at 5:50 PM on May 12 [2 favorites]

Noctex if you're comfortable running a little gothy. The skinny joggers are really excellently flattering.
posted by snaw at 5:59 PM on May 12 [9 favorites]

Also, I like Nordstrom's house brands for casual wear--though a lot of it is wovens or things with traditional waistbands and other sorts of clothes which will fall outside the stretchy parameters.
posted by crush at 6:00 PM on May 12 [1 favorite]

I love Smoking Lily for soft, stretchy, comfy but nice looking clothing. Their stuff is handmade and lasts.
posted by hurdy gurdy girl at 6:05 PM on May 12 [3 favorites]

I’m around your age and have recently been working on the same issue. In my case it has to do with looking better in clothes that are more tailored/structured — I’m short and somewhat broad shouldered so anything boxy or shapeless makes me look frumpy.

I’ve found things I like at Athletica, Title 9, Lululemom, Eddie Bauer and Outdoor Voices. For me the key is bottoms with wide waistbands and t-shirts that narrow at the waist or are high/low or have front twists. I also find jogger style pants (which now come in a number of weights/fabrics) to be more flattering and versatile than leggings or other styles of casual pants.

Finally, it might be worth downloading the Nordstrom app — they have a pretty good shopping interface, you can go to the “activewear” dept and then filter a bunch from there. Plus shipping/returns are free.
posted by mrmurbles at 6:12 PM on May 12 [1 favorite]

Uniqlo has very comfortable and very affordable pieces that look great. You very much have to try some of them on though- not everything will fit right. It's sort of a well made but casual look- I have several of their summer dresses, and I'm not a dress person but they are so comfy I make excuses to wear them when the weather is right. Their pants are also very comfy, in a wide variety of styles (sweat/jean/slacks etc) They have nice comfy print tees now that look very upscale but very soft. In the fall you should be able to find casual blazers as well.
posted by Homo neanderthalensis at 6:22 PM on May 12 [7 favorites]

Betabrand makes "dress yoga pants" and well as other clothing. The Soft Surroundings catalog is very much a cozy, unstructured, grown-woman-in-Santa-Fe-having-brunch aesthetic. (Both will send coupons and discount codes if you surrender an email address.)

Though I also think you should shop, in person, at like a Nordstrom-type place. There's been such an upswing in retailers adding stretchy fibers to their wares, offering a 'performance wear' element to clothing -- a lot of what you might be consigning to the mental rubbish bin as 'stiff' would be a pleasant surprise, once it was tried on. 'Sharper' generally means more structured. It's hard to 'sharpen up' activewear and sneakers, but softening up dark-wash jeans and euro-style flats has already been done.
posted by Iris Gambol at 6:29 PM on May 12 [3 favorites]

Are swing dresses an options for this? With leggings underneath. Can do short sleeve or sleeveless swing dresses with capri leggings. Super comfortable and looks like you tried.
posted by Kalmya at 6:34 PM on May 12 [1 favorite]

Almost 50 here, and I swear by Girls of a Certain Age. Some of their featured products are too expensive, but not all.
posted by frumiousb at 6:50 PM on May 12 [1 favorite]

I love Stitch Fix for problems like this. I'm awful at looking like a grownup on weekends if left to my own devices, but they send me stuff that is not what I'd choose for myself yet perfect.

I've also tried to do nicer athleisure stuff and tbh it's ok for very casual outings but it really doesn't look good, it's just Better Than Sweats, which is not much of a standard.
posted by gatorae at 6:53 PM on May 12 [2 favorites]

All the pants I have like that come from Athleta.

Try a pair of linen pants with sandals and a cute top for a comfortable, casual, and summery vibe.

I'm partial to joggers with on trend sneakers and a slightly structured shirt, but it's a somewhat younger looking style so ymmv.
posted by asphericalcow at 7:06 PM on May 12 [1 favorite]

If you look great in business attire, then you must already have a good understanding of what works for you in terms of cut and color, etc. So I think the reason you're stumbling a bit here is that, well, "sharp or stylish or quality" is hard to square with "sweatpant-type" if you no longer have the build of a woman in her 20s. One can argue the pros and cons of athleisure, but there's no doubt that it works better on a slender and perky physique. 40s is tough because you're having to decide at what point you're going to give up and just do Eileen Fisher-style, and that's a very personal and idiosyncratic transition. You can get "quality" and "comfortable" once you travel down the EF path, but sharp or stylish become very elusive. Call it the patriarchy, but there we are. A more casual dress may help you reconcile the competing imperatives; that Kapow dress at Smoking Lily looks good, or Boden has some lighter jersey dresses that would also work for the casual weekends. (I'm a life-long resister of dresses but in recent years have been forced to concede that they can be an okay casual option.) Accessorizing helps a lot here, too--good-quality but not excessively serious longer necklaces or stacked bracelets or playful scarves will tighten the look without making it too uncomfortable. For shoes, good ballet flats for dresses, or classic low-cuts like Supergas for jean-type outfits. And don't forget how much of a role makeup can play. You probably have a nice standard subdued professional makeup look. I am not saying go sparkly-crazy on weekends with it, but instead of just skipping it, try doing something a little more interesting. A good manicure helps, too. There are so many more interesting colors that you can get away with even at work these days...
posted by praemunire at 8:04 PM on May 12 [2 favorites]

I'm not sure if "tennis shoes" means fashion sneakers like Converse or old-school Adidas or if it means more like trainers/running shoes.

I'm of a similar demographic, and when I say "tennis shoes" I mean something along the line of Keds.
posted by The Underpants Monster at 8:11 PM on May 12

Sperry topsiders.

Basic cotton t shirt dresses from old navy with 3/4 length sleeves. Multiple because on sale they are like $12-30.

Pair the above with your nice work handbag or a decent longchamp style tote and a cute necklace.

Talbots has gotten way cuter. So much cuter. I don’t think it is just because I’m getting old.

Shirt dresses are great for this. Pair with flip flops. Nice ones.

A nice pair of skinny jeans. Pair with graphic tee. Cardigan.
posted by slateyness at 8:37 PM on May 12 [2 favorites]

An easy way to update a casual outfit these days is to wear white sneakers. Even future royal family members are getting in on it.
posted by BusyBusyBusy at 4:38 AM on May 13

A nice pair of skinny jeans. Pair with graphic tee. Cardigan

Popping back in to note that this is my casual uniform. I’m 42. I think the keys here are well designed graphics tees and an interesting cardigan. I like Cotton Bureau for tees. My latest cardigan is a bomber jacket shaped wool zipper cardigan from Mountain Hardware.

In the summer I wear hiking shorts with my graphic tees.
posted by jeoc at 7:03 AM on May 13 [3 favorites]

Another nearly 40-something woman here reporting that she feels both comfortable and classy in an outfit that includes stretch jean leggings (seriously, those ones are cheap, but I love them), soft t-shirts or tunics (honestly, I just pick out what I like at places like Gap or Old Navy), a drapey open front or cocoon cardigan (like this), and a pair of sneaker-ballet flat shoes (like these).
posted by pinkacademic at 8:28 AM on May 13

Noctex if you're comfortable running a little gothy

OP said they avoid black because they don’t look good in it.
posted by MexicanYenta at 8:35 AM on May 13

Noctex if you're comfortable running a little gothy

OP said they avoid black because they don’t look good in it.

They carry plenty of non-black items.
posted by thegreatfleecircus at 9:10 AM on May 13 [1 favorite]

*gasp* Goth stereotyping!

I know I was talking up dresses further up-thread, but personally I usually wear jeans (the cut that suits me, which is not skinny jeans, but thank God is not so crazily out of style as to permanently date me--this is a fine line to walk, between that which best flatters you and that which is most up-to-date-looking) and a very slightly obscure t-shirt ("H*ck the system," anyone?) and a cashmere hoodie. A hoodie in a nicer knit is a bit more adventurous than a cardigan, which drifts you back towards officewear. Supergas. A scarf if more color or warmth is needed, which it often is.
posted by praemunire at 9:39 AM on May 13

Leggings, jeggings or capri-length leggings, long tank top and a drapey cardigan or hoodie. Uggs, ballet flats, cute sneakers or flip-flops. Swing dresses in the summer. Jewelry or bag to emphasize formality level.
posted by Pax at 10:02 AM on May 13

I'm 41, and count me in on the dress + cardigan and/or leggings depending on the weather bandwagon. Sneakers (Chucks are super cute with dresses!) or flip flops or nicer sandals or boots, depending on the formality level. Scarf if I'm going to be in aggressive AC or it's going to be colder, either matchy matchy with everything else if I need to look nicer or deliberately pattern matching but complimentary colors if I'm looking more casual. Jewelry if I actually need to look like an adult. Knit dresses will take you 90% of anywhere you need to go on a weekend (or weekday, for that matter) anymore.
posted by joycehealy at 2:51 PM on May 13

I just got a pair of great jeans, not super skinny, not very low in the waist, from Eddie Bauer. They are comfortable but look good. I tried on @ 30 pairs of pants, bought 2 pairs of jeans. Wear nice shoes or sandals that are well-maintained. I have a pair of turquoise keen sandals that are as comfortable as sneakers but just a bit nicer looking. Shop hard for great footwear, as it's a subtle but important indicator of status. Buy plain, nicely cut t-shirts. I have some from J.Jill that look great and are comfortable. The typical crew neck isn't universally flattering.
posted by theora55 at 5:43 AM on May 14

I agree, this is an interesting question!

So I have a pair of Starfish trousers (elasticated waist -- ooooh yeah) by Lands End that work very well for casual but not too casual when paired with a jersey top.

I love stripey tops - they're just a smidge more interesting than solid block colours, more grown-up than a slogan tee (not that you need to look grown up!), and depending on colour combination they can be either fun and wacky or sedate and classic.

I also favour a nice jegging with a longer drapey t-shirt. But I don't find jeans/jeggings as comfy as my Starfish trousers.

And seconding the recommendation of superga or another brand of low cut trainers.
posted by Ziggy500 at 7:40 AM on May 14 [1 favorite]

Original poster did not mention size, but I am here to recommend Universal Standard to anyone and everyone (sizes from 6 to 32). I recently got two of their "kits," the Essentials (tank top, leggings, skirt, long-sleeve t) and the Loungewear (cardi, pants, "nightie," slouchy top) kits.

Fantastic quality, true to size, so easy to shop for! The loungewear stuff is SO soft; literally the softest, most comfortable stuff I've ever worn. Everything is well-made, and it washes well (I machine wash in cold water and then hang to dry), so I know I'll get years of use out of these pieces. Can't recommend highly enough!
posted by Groovymomma at 9:59 AM on May 14 [3 favorites]

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