Posted on 42 Comments

Fashion victim


Ok, who wants to help me be a little less winter-fashion-inept?

I am reasonably comfortable dressing myself in the warmer months, or pulling together an outfit around a pair of jeans, but in the winter, anything not jeans-based throws me for a loop.  I always end up feeling like I’ve chosen the wrong footwear and “frumpified” the whole outfit.

So here’s the challenge: Neil bought me the most comfortable pants ever for Christmas.  And when I say comfortable, I mean that I wore them for several days until Neil made me wash them. That comfortable.  I ordered a second (ok, and a third) pair last week so now in addition to my original charcoal gray pair, I have two black ones.  Here’s what they look like:


These are great flip-flop-wearing pants in my opinion, but that kind of weather is still several months off.  What do I do right now? It’s too cold to be without socks.  What kind of shoes work best here?

I could see dressing them up with some nice heels, a cotton blouse, a fine-gauge sweater, and a linen scarf for a night on the town, but that’s not what I’m after at the moment.  I want to wear them with a t-shirt, a nice hoodie, and… what? sneakers and tube socks? mary janes and argyle socks? black flats and gray socks?

The goal here is to be comfortable and casual without looking too dressed-up, too dressed-down, or 20 years older than I am.  Especially that last one.

Please educate me 🙂

Posted on 42 Comments

42 thoughts on “Fashion victim

  1. my vote is for some cute Danskos or Sanitas.

    1. Ooh, I have a pair of Danskos! I wasn’t sure what I thought of the brown shoes with the black pants, though, and I’m still not sure about socks… what do you think?

  2. Boots!

    1. Boots never occurred to me… inside or outside the pants?

  3. Some short boots or ballerina flats would work well.

    1. I definitely can see them with ballerina flats, but I’ll have to wait for spring, I think. I definitely need socks for winter around here.

  4. I would wear those with my heavy duty Mary Janes for cold but zero precipitation days (with cute socks..but I’m a sock addict) or Doc Martins (or my knockoff Doc’s as it were) for snowy days.

    1. My heavy-duty maryjanes are brown… think I need a black pair?

      1. yes I think black! There is nothing better than the perfect pair of super comfy pants…I have one pair, they no longer make them anymore. I’m eying me some of them you’re wearing now 😉

        1. I’m perusing eBay as we speak 🙂
          These pants are sooooo nice. And they’re marked down from $50 to $15, which is a bonus!

  5. What style/type of pants were they? They look uber comfy!

    1. They’re stretch pants from Lands End. There’s a link in the post – they’re on clearance right now and marked way down!

  6. I love Toms with all of my casual outfits. They are comfy, come in lots of fun colors, & look cool without beimg too fussy. Red ones would be great with them & a neutral sweater & scarf!

    1. I was toying with the idea of red shoes… I love the Toms philosophy. Wish I wasn’t such a cheapskate about shoe-buying, though. I have a mental block about spending $50 on canvas shoes, even though the cause is a good one.

  7. Oh heavens, I’m not a fashion plate either, but I am a shoe junkie! Here are some suggestions:

    On a Lands End kick, how about these?

    A little higher in price, but so, so cute & comfy (and sparkly !)

    These are nice all-purpose booties with good soles for weather (if we ever get any)|so0005|2052&prev=hp!sf!2052

    1. I’ve had my eye on Lands End clogs for some time. Have you seen the deep orange suede ones? Yum!

      And those patent leather ones? *love* Wish I could stomach that price!

      1. I’ve bought Lands End shoes before, and they’re pretty good. If they had those gunmetal clogs in my size, I’d have ordered them right away!
        The patent ones are on my wishlist, as they would go as well with jeans as with dress pants.
        I bought a nice pair of BOC clogs at DSW that look a lot like the plain Danskos, but at a much lower price.

        1. Those look just like the Sanitas I bought on eBay last night. I hope they get here before the weekend 🙂

          I have several pairs of Lands End shoes, and they have served me well. I wear a pair just like these a lot.

      2. Go ahead and spend some money on Land’s End shoes; they are well made and worth the money. I have a pair of loafers I bought as seconds in 1980 and I am still wearing them. They are my favorite running around shoes. They have been resoled twice, and the body of the shoe is holding up well.

        1. Oh, I agree. I’ve been buying Land’s End shoes for a few years and I love them – they’re as nice as the day I bought them. The ones I was moaning about price on were $134 patent leather clogs at Nordstrom. Just can’t make myself spend that!

          P.S. 1980? Wow! I have a brother younger than those shoes, LOL!

  8. If socks are a must, i would say either short boots or long boots over the top.

    1. Thanks. I think they’re too baggy for long boots over the top, but short boots would work.

  9. In Montana, winter clothes are jeans, boots or tennis shoes, a sweater with possibly a tee underneath. That’s it-the uniform.

    1. Yeah, that’s pretty much my look most times. But I find jeans so uncomfortable lately – they just aren’t made for my shape – so I’ve been exploring other options 🙂

  10. Lisa, I have 4 pair of Skechers slip ons. I love them. They can be dressy or casual and I can walk forever in them.

    1. Worth exploring – thanks! 🙂

  11. Ok Lisa here’s my input 😉 Mary Janes with cute “knitted” socks, Cowboy boots with pants over them, and of course Ugg boots or something similar, pants in or out depending on how “baggie” they look tucked in. Can’t wait to see what you decide.

    1. Love that knitted sock/maryjane look. You put knitted in quotes, but I really want to get my act together enough to knit a pair of socks to go with my maryjanes. I’ve started twice, but never gotten more than 2 inches done. Someday!!

      I think my feet would sweat to death in Uggs 😉

  12. Wanted to put my two cents in early this morning but had to research and then order a pair of the pants and a top to go with them first! By the time I looked at all of the sale items and made my decision, it was time for me to run ( figuratively ). Anyway, I like the little flats the model was wearing with the pants and just happened to have purchased a pair of retro styled Sam and Libbys a week or two ago….perfect. I also think they will look great with a pair of grey suede Clarks that I own. They are a slip on with elastic lacing – very comfortable for walking. Love the clogs with handmade knit socks idea too. No lack of options.

    1. How funny! I hope you like the pants as much as I do! I think the ballet flats on the model are nice, too, and I’d go that route except I really need something warmer at this time of year.

  13. Good Morning Lisa,
    I think you should get a pair of Keen Harvest II Mary Janes. The sofest,stylish, and most comfortable shoes.(better than house slippers) Get them a size smaller if you wear thin socks, or none at all. Half size smaller for thick socks. These shoes run large.
    I am new to your website. Love it!!! I really love your polymer clay work.
    Keep up the good work.

    1. Those are really interesting shoes – very artsy! Thanks for the complement re: my claythings. Thanks for dropping by!

  14. harder soled “ballet-style” flats, Toms, Rocket Dog or Born mary Janes, converse (always in style no matter how “old” you are), Slip on Keds…

    1. I have a pair of red converse that I was thinking of trying with these. Thanks for reminding me! I thought about ballet flats from the beginning, but I prefer to wear those without socks, and right now it’s too chilly for that. In the spring, though, definitely.

  15. These are very nice pants, which can be easily dressed up or down. I love versatility! Mary Janes would be my choice for dressing up; low heeled boots (pants outside) for dressing down.

  16. Are you opposed to all heels on principle? I know lots of people are, but I’d be inclined to wear those with boots or cute heeled oxfords (lace-up shoes).

    I also live farther north than you and would be unopposed to wearing them with heels or flats (Mary Janes or otherwise) without socks; as long as the rest of me was appropriately warm, the two inches of skin I would be showing wouldn’t bother me. But based on the length, I’d go with something taller (either chunkier, like Docs, or higher, like heels), rather than a ballet flat — you don’t want to wear out the hem.

  17. Sometimes, I should click the link before responding. I didn’t realize they were stretch pants. I take back everything I said except for the “taller” business and now recommend sneakers or Danskos.

    1. Gotcha 🙂 I just bought a pair of black shoes, very similar to the Danskos I’ve seen and they are doing quite nicely, I think.

  18. FREE SHIPPING! I went to the site and ordered a pair of the pants, and then googled for a promo code and lo and behold, free ship for the next day or so at least. (But the pants are backordered until 3/01. I will remain in jeans until then.) Thanks for the link.

    1. That’s great! I got free shipping on my order, too, but I needed a minimum order of $50. Not that it was much of a hardship to load a few more items into the cart… 🙂

  19. Clogs.Definitely.

    1. Agreed. I got a pair and am liking them a lot.

Leave a comment!

This site uses Akismet to reduce spam. Learn how your comment data is processed.