Weekend Wednesday: What Are Your Weekend Sneakers — and Why?

what sneakers do you wear and why

For today’s Weekend Wednesday, let’s talk about sneakers…specifically, which sneakers do you wear, and why?  Obviously sneakers are not appropriate at most offices unless you’ve got a very casual office. But almost everyone needs a pair of sneakers for the weekend (whether you’re canvassing for office, hitting an outlet mall, or just having brunch). And I’m always interested by how many women, myself included, sort of have a base sneaker that you choose again and again for “fashion” more than any athletic purpose. For me it’s Converse, which as I’ve noted, I’ve always associated with a wacky, outsider, sarcastic kind of persona — the kind of persona that I really identified with in my youth. I’ve stuck with Chucks, even though they don’t feel 100% me anymore, in part because the other sneaker brands feel even less like me since I have associations with those, too. Keds = My Grandmother. Vans = My friend J. (Nothing against J; they look great on him — they’re just not me.) (And today’s question honestly has nothing to do with judging other people — it’s more like the Amy Poehler idea of “good for you, not for me” — there is no right answer because obviously all of the different sneakers are hugely popular. I just think it’s interesting how we identify different personality traits or style personas with different sneakers, sometimes very strongly.)

On the flip side, there are newer, more fashionista-y sneakers coming down the pike every day — these days it seems like everyone wants a blush-colored sneaker from brands like AllBirds, Everlane, and Eytys. (If you definitely consider yourself more of a fashionista/sneaker-purchaser I’d check out Net-a-Porter, ShopBop, or possibly J.Crew (lots of trendier, exclusive colors for Tretorns, SeaVees, and New Balance particularly) — but I’m curious to hear what other shops and brands you love for fresh sneakers also.)


So, readers do tell, which are your favorite sneakers for the weekend? What do they signify to you? How do they play into your weekend persona when you’re not at the office? What are your associations with different sneaker brands? Have you ever changed your “base” sneaker and started wearing another brand (or do you own several of these sneakers and move among the brands)?

Pictured above (by color), Row 1: black / gray / gray / white; Row 2: white / white / green / black
Pictured above (by brand name): Row 1:  Converse / Vans / Superga / adidas Stan Smith; Row 2Keds / SeaVees / Tretorns / New Balance

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What sneakers do you wear -- and why? Even women lawyers, bankers, and others want to look fashionable but be comfortable over the weekend, and Kat thought it was interesting how LOYAL people were to different brands -- you're a Chucks girl, or you only wear Keds or Superga, or you're always seen in your Vans. Fun discussion with the readers about what sneakers they wear on the weekends -- and why?



  1. I love my slim Vans. I get a new color every year, this year is gray, last year was navy, the year before had a galaxy pattern on them. I’m allowed to wear them to work too which is just so awesome.

    • Slim vans :

      are slim Vans different than regular ones? having trouble finding them with that description, but it is exactly what my narrow foot needs. TIA!

      • AnotherAnon :

        If K is referring to the Lo Pro’s yes! I have Lo Pro’s and the sole is about half the thickness of the original. Width is about the same.

  2. Anonymous :

    Er… my running sneakers. I have a pair that just did not work as running sneakers (they give me terrible blisters when I have orthotics in, but are otherwise fine). Rather than just throwing money away on them, they are weekend footwear.

  3. m gemi cerchio :

    I’ve been looking at the M Gemi Cerchio. Anyone have a pair? They are spendy, but look lovely…..

  4. Anonymous :

    Adore my Allbirds.

  5. Anonymous :

    I love my Skechers Go-Walks. I have a lot of foot issues and they are the only sneakers I can wear comfortably because the sole is so heavily padded and cushioned.

  6. Gucci Ace sneakers with the bee. Unbelievably comfortable. Cost an arm and a leg but since they are my only sneaker, I got the cost per wear down very quickly. (I used to wear them also on casual friday if no interviews)

  7. My current favorites (for the past year or so) are Tretorns, because:
    1. I’ve discovered that Swedish brands fit my feet (narrow heel, less narrow ball) well–I blame the genetics of my Swedish-heritage grandmother.
    2. The insoles are a bit cushier than a lot of other “fashion” sneaker brands
    3. The price point seems reasonable to me

    • Anonymous :

      I love Tretorns, mainly b/c I grew up in the 80s in a vaguely preppy part of NJ (or solidly working class with preppy aspirations). I actually played tennis in them (while wearing a headband).

      So glad they are coolish again — may pencil these in for the summer since the Natives that look like these didn’t work on my feet.

    • Thanks for the recommendation! I’d never thought of trying Swedish brands, but that’s a great idea.

    • Anonymous :

      Tretorns were the preppy thing when I was in middle school (a really long time ago). They make me nostalgic, but I’m not sure I could wear them again. Funny how these things cycle.

  8. I have these in “Warm Grey Leather” and love them.


    • Senior Attorney :

      LOVE those! My husband has a pair of black Eccos that I love and for some reason it never occurred to me that they had them for women, too!

    • Anonymous :

      Ooo I really like those. Do we think the blush trend is going to be around for a while? I’m seriously considering getting this shoe in blush but it’s a little spendy for a trend.

      • The blush pair is amazing. Even if it goes out, it’s relatively neutral enough that you could still get a lot of wear out of them. Personally, I hope blush stays around for awhile. It mixes so nicely with grays, navy, and black, all of which are the foundations of my wardrobe!

  9. The JCrew New Balances – relatively sleek but still supportive. They fit well with my tailored personal style.

    • Baconpancakes :

      Me too. I don’t always get the J.Crew collab ones though – New Balance makes the same 620 sneaker in different colors, and those are usually more muted and neutral, and go with everything. It’s definitely NOT a running sneaker, though – the one time I forgot to bring my running sneakers, and figured I’d just work out in my 620’s, I got terrible shin splints.

  10. The Roxy Bayshore sneaker in beige canvas. When my dog ate my first pair, I liked them so much I got another pair.


    And Keds Crashbacks in brown.


  11. Chucks. Always Chucks.

    • Not that Anne, the other Anne :

      Seconded, with the specification that they must be something other than black or white. I have had black and white polka-dots, sky blue, green, etc.

  12. Do my Toms count?

  13. Anonymous :

    I have had a pair of leather Eccos for a couple of years. Great for running around town, but am getting something with more support for upcoming trip to Europe — they were not great on my last trip there three years ago.

  14. slip on style leather sneakers usually steve madden, I have black perforated leather, millenial pink suede perforated leather, metallic leather, a pair of high top side zip navy booties(sam edelman), ecco sneakers that slip on but zip in a matte suede, I have adidas sambas, and red stretchy converse, white converse that do not get much wear. I can wear sneakers to work, so I have alot, I like dark straight jeans, plus stripey tee, and knit blazer, or scarf. Plenty dressy for my hoodie acceptable office. Some of the sneakers go well with dresses without tights.

    • I also have Adidas Sambas! I onley wear them on weekend’s b/c they do NOT look good with a dress on. I have NIKEs that I walk to work with. Men like me in Nike’s for some reason, but I prefer the Sambas! YAY!!!!

  15. Anonymous :

    I got a pair of Naturalizers from Nordstrom and they are incredibly comfortable. I’m considering getting another pair.

  16. Various pairs of Toms, a pair of all ivory (leather on patent) pumas, and ivory quilted new balance with a rose gold N, palm-print bucketfeet slides….I have no idea how I’ve collected all of these.

  17. Anonymous :

    My sister moved to my city recently, and like she has my entire life, she has stolen all my friends.

    Thank you. I have to vent but am not allowed to complain anymore. Yes, I realize all this is dumb.

    • Frau Anon. Y. Maus :

      You should complain! I feel your pain, lady. Wasn’t there a movie with Malin Akermann being that lucky sister and taking everything that Katherine Heigl ever wanted?

      Curious- did you keep your sister away from your friends, knowing your history, or was it unavoidable? I can’t imagine my friend group all latching on to one of our sisters so quickly.

      In any case, commiserations and chocolate aplenty from us!

      • Anonymous :

        I really cannot complain anout anything (my mother being ridiculous, normal spousal whining, etc) anymore. Trust me when I say, not an option without me coming across as a jerk.

        And no, didn’t block her because I’m a kind, supportive sister. Part of it is that she is child-free, as are they, and works more normal work hours- so she’s like the more available version of me.

    • Elegant Giraffe :

      ohhh super annoying! not dumb to want to vent.

    • It’s not dumb! That sounds like a tricky and difficult dynamic.

  18. Related question- what do you wear with your sneakers on the weekends? I wear jeans on the weekends, but jeans and sneakers (even, or maybe especially, fashion sneakers) reads high school to me. Am I wearing the wrong jeans? Most of mine are dark wash straight leg. The wrong sneakers? I’ve tried with low top converse and some patterned Keds. Or is this a mental block that I’m being crazy about and my jeans and sneakers actually look fine.

    • The only way I wear sneakers with jeans is during warmer weather when I roll up the ankles of my jeans a bit for that boyfriend look. I’m like you and can’t do sneakers with just plain jeans down.

    • Anonymous :

      You’re being crazy.

    • S in Chicago :

      I like straight leg jeans with something a little fancier like the oxford-sneaker hybrids around (Cole Haan, Munro–I know there’s some others). But maybe that’s just because I’m more inclined to do a straight leg jean at work vs. weekend/tighter jeans on casual days?

    • If I wear sneakers, it would be with sundresses or otherwise feminine outfits to balance it out a bit. Think riviera style subbing espadrilles for sneakers. I never wear sneakers with jeans because it makes me look younger than I’d like to be perceived.

    • I do them with skinny jeans rolled up a little (although I know it’s been said on this board that rolling jeans is out) and I also like them with barely boot jeans. Super flared jeans, which I still own, would read high school to me, but my dark wash, barely boot jeans seem a little more sophisticated. I hope.

    • I don’t think you are crazy, and I think it depends on where you live. Some areas are little more dressy, even on weekends, and one might feel out of place in jeans and sneakers. I prefer jeans with short boots, but where I live, I don’t wear jeans when it gets much warmer than maybe 70 degrees, because it’s usually also humid enough to make jeans unpleasant.

      And some of us just aren’t sneaker people. A few years ago I did find a pair of Jambus that are black leather with perforations that I like and feel relatively comfortable wearing, physically and psychologically. But otherwise, I don’t love sneakers.

    • Pretty Primadonna :

      I wear my sneakers (Chuck Taylors or low profile Sauconys (ies?) (I love these so much, I am on pair two and considering buying pair three–all black)) with leggings and tunics, or athleisure, or casual dresses. I prefer booties or sandals or heels with jeans.

    • I don’t like to wear sneakers on the weekends during the winter unless I am going to the gym. I just feel like long jeans and sneakers look sloppy, even if they are skinny jeans. Instead I wear flat ankle boots. But I wear sneakers all the time when it is a bit warmer and I can show some ankle. I think it looks more stylish and intentional.

      I do wear sneakers for commuting to work every day though. I really don’t care how it looks – I need to be comfortable to commute in NYC. The color and material change depending on the season. Right now I am wearing grey leather Nikes that are more street shoe then gym shoe.

      I bought the light grey Adidas courtside sneakers for spring. In the summer, I will switch to canvas sneakers.

  19. Anonymous :

    Taos Star. I now have three colors. It has the best arch support of any fashion sneaker I have ever tried and I can wear them for hours with no issues. And I have lots of foot issues, including high arches and a delightful hammertoe. Worth every penny.

    • Oh, these look promising. I’ve got a slightly narrow heel, slightly wider forefoot, and a tendency towards plantar fascitis so arch support is a must. Did you size up- reviews say they run a bit small? For running shoes, I go up a full size, but maybe a half size on these?

      • S in Chicago :

        Try Vionic, too, Mascot. Your feet sound a lot like mine. A day of wearing Chucks or Vans and a lot of walking would leave me with weeks of heel pain. Vionic has some fashion options that are truly walkable–they’re my go-to for travel.

    • L in Sacramento :

      Just bought my first pair. In orange. Hope they feel good cuz they look fantastic.

  20. Ehh I gave up on the hunt for cute weekend footwear. Now I just wear my hiking boots. I’m debating buying hiking shoes to wear on the weekends even though they’re kinda dorky. For me #momlife means caring more about being comfy than looking cool. It’s not like I go to brunch anymore anyway, ha!

    • Frau Anon. Y. Maus :

      I love hiking shoes for uh… hiking and general walkaboutery on grass, pavement etc but find them heavy, especially on hard floorings such as airports and malls. I also never wore them between April to December because they (to me) looked stupidly unseasonal and I thought they might be super warm and sweaty. What brand do you wear?

      • They are North Face hiking boots that I bought in 2006 for a trip to Big Bend. They look kind of like this: https://www.zappos.com/p/the-north-face-hedgehog-fastpack-mid-gtx-dune-beige-deep-garnet-red/product/8711451/color/663259
        They are kinda heavy TBH, but I’ve only worn them in the Winter so far; they would be way too sweaty in the summer. I’ll probably go back to Nike running shoes when Spring rolls around.

  21. Housecounsel :

    I don’t wear sneakers with jeans, unless you count the slip-on Toms sort of style. I might throw those on to go pick up the kids. I do love my New Balance 247 in this amazing shade of burgundy, purchased from Athleta. However, I only wear them with yoga pants. In the winter, I wear my jeans with Sorel lace-up boots most of the time.

  22. I love the Reef Rovers for more casual sneakers and ColeHaan zerogrand for a touch nicer

  23. Metallica :

    I love my Supergas with a slight platform–took a bit to break in, but worth it, and they look nice in leather. I have occasionally worn them to work if I’m only doing administrative stuff that day.

  24. My weekend sneakers are leather flats. Sorry not sorry

  25. I have an embarrassingly large number of weekend/dog walking sneakers . . .

    I rotate through three different pairs of Shoreline Converse (oatmeal, teal, and grey), two pairs of Toms (natural with black polka dots and grey), and a pair of NB 574s that are hot pink, orange, and purple (they are kids shoes).

  26. Anonymous :

    Can someone clue me in – when did fashionable sneakers become a thing? I thought we were all about ankle boots? I totally missed the memo on this one.

  27. I have a pair of keens that look like chuck taylors that I love. I also love the look of the new balance 574s but I don’t really need another pair of non work out sneakers at the moment. But it might be those when I do.

  28. Anonymous :

    But what do you wear with sneakers and jeans? What kind of top do you need to make this a cute outfit? I have this dilemma every time we go on vacation because I want to wear sneakers if we’re walking a lot, but then I feel like I have absolutely nothing to go with them. HELP!

    • Usually, I am wearing skinny jeans and a loose, flowy top for balance. Depending on the temperature, that means either a 3/4 sleeve scoop neck (I have it in several colors) or a racer back tank and one of my loose Bobeau cardigan-type things.

      If I am being lazy, I wear them under my flare jeans and one of my zip up fleeces or “fancy” sweatshirts. Note, this is not the stylish look.

    • Senior Attorney :

      It sounds silly to say it, but… a cute top! It also helps to throw on a third piece like a vest, a jacket, a scarf, or even a necklace. I am all about striped sailor tops by YMMV.

  29. Can anyone speak to the Everlane street shoe? I have wanted to buy them and like the look.

  30. Lana Del Raygun :

    I really like Keds! I used to think of them as grandma sneakers and then I discovered that they are (also) swing-dancer shoes, partly because of the soles and partly because they look cute with dresses.

    • I’ve worn keds since grade school, which I obviously attended with someone’s grandmother. About 3rd grade allegiances had to be decided – Keds or PF Flyers. I chose Keds. I keep them in black, red and navy.

  31. I love my Rockport/ Cobb Hill leather sneakers. Model is the Willa. So comfortable, lots of arch support and pretty darn on trend for rockport… link to follow.

  32. https://m.shop.nordstrom.com/s/rockport-cobb-hill-willa-sneaker-women/4664798

    Mine are black leather. Love!

  33. Yeah. I guess that I’m someone’s grandmother too. <3 my keds. The white reads granny-ish to me. I have a black and navy pairs. I've been thinking about getting red.

  34. Love Reading corporette, it’s a culture shock everytime. I’m from tretorn country (ie Sweden). I’m 40+, in finance and I wear a black blazer, jeans, silk t-shirt everyday. Meetings, interviews, events. And sneakers. Everyday. Eytys or Nike cortez in black suede, or vans style in black or burgundy. Snowy days = black mini uggs. On the rare occasions I wear high heels or ankle boots I wear a distressed cotton t-shirt under the blazer to balance it out. It amazes me how swedes are so uptight with manners and etiquette, and so low key in fashion. While most americans I’ve met are open and easy going but US Corporate dressing is a complete puzzle for me to understand!

    • I was just running through this thread again for ideas and saw this. Welcome and hope you will post more!

  35. I love my grey Pumas. I used to never wear sneakers – except to the gym – but, after rupturing my Achilles’ tendon, I am looking for cute AND comfortable. And these are it for me: http://us.puma.com/en_US/pd/vikky-softfoam-womens-sneakers/pna190274405295.html

    I also dig my Chucks.

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