Outfits STYLE // Winter

What about the ‘shoulds’?

March 9, 2017

[ merino turtleneck, Goodwill (similar in cotton, similar in wool) | skirt, Steven Alan via Crossroads (similar, made in NYC) | tights (similar) | boots, Everlane | bag, Cuyana | cuff, FashionABLE ]

Don’t let the smile fool you. I don’t love this outfit. But instead of scrapping this post, I realized it sent me down a line of thinking that I should share here on the blog.

Sometimes I wear things because I feel like I ‘should.’ I don’t mean in the sense that I should for the blog, but more like I should in my daily life for reasons like: ‘variety’s sake.’ I’ve donned dresses and skirts a fair amount over the winter, but I really have to push myself to do it. And most of the time it’s to assuage some vague feeling of obligation. Like I should be wearing my skirts and dresses more because they’re just collecting dust in my closet all winter.

But maybe that’s a faulty line of thinking. Perhaps it’s better to stick with what I love and wear pants to my heart’s content all winter. When do we say ‘yes’ to pushing ourselves outside our comfort zones? And when do we say ‘no’? 

I realize I said that dresses and tights were part of my winter uniform, but I am starting to wonder if that was more wishful thinking.

Overall I’d rate this look a B. I think the green tights are fun, and bring a subtle variety to the color palette. But would I reach for this outfit for an important day event? Probably not. Would I be quick to pack the outfit if I was headed out of town? Not so much. I love the pieces, especially this skirt, it’s a favorite of mine in the summer. But something isn’t quite working for me.

Do you wear things because you feel like you ‘should?’ Where do we draw the line on what we wear because we feel like we ‘should?’


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  • Rebecca March 9, 2017 at 10:15 am

    Hey Andrea!

    I hear ya, up through this year, I wore dresses 98% of the time during the summer… and 0% of the time in the winter. I think that’s fine. But this year, I started wearing dresses in the winter! And I really liked it.

    I found that, for me, two things were preventing me from wearing more dresses in the winter:
    1) things that I loved to wear under them (I am not a tights person — I need comfy, thick leggings)
    2) the idea that my summer dresses can (and should) pull double duty in the winter

    After (finally) finding the right underlayer for me, I pushed myself to wear a few of my summer dresses this winter, in addition to the two I added to my closet specifically for winter. What I found: I always felt meh about wearing my summer dresses for daily use — but my new winter dresses got a TON of wear.

    My lesson: I love things that pull double duty. I want my wardrobe to be versatile. But, when the seasons are 80 and sunny versus 40 and raining (also a PDXer) — it’s a rare dress that does daily wear well for both. Rationally, that makes sense.

    For me, I’ve accepted that it’s asking too much of my clothing to do both.

    Thanks for sharing! Rebecca

    • Andrea March 12, 2017 at 11:03 pm

      Hi Rebecca! Thanks for weighing in! Did you get colored leggings? I find that another obstacle for me is the ‘all black’ problem.

      You make a great point about summer dresses! I think too often I am trying to make things work year-round, and there are some things just better left for their respective seasons. Thanks for reminding me! You’re right, we do have a pretty wide range of temps.

  • T March 9, 2017 at 10:36 am

    I pushed myself to wear dresses this winter and I’ve been loving it! I’m also in the PNW and I’ve found dresses to be wayyyy warmer than jeans. I have thick cotton tights and warm ish waterproof ankle boots. I haven’t even tried to wear my summer dresses in the winter. Instead, I wear sweaters over my fall dresses and I have some thick quilted dresses that I love! I’ve basically been wearing the same six outfits on repeat for three months now and am looking forward to spring to switch it up.

    I’ve been really struggling with sweaters this winter though with how much colder it has been than usual. I’m allergic to cashmere and wool so it is quite frustrating trying to find sweaters!

    • Andrea March 12, 2017 at 11:05 pm

      Yes, wool tights does equal super duper warm! I think I just feel too fancy in tights sometimes. Maybe if I had some clog boots it’d be different…. ;) Six outfits, I love it! Must make getting dressed a breeze! Hearing you say that almost makes me miss capsules. It’s a good reminder to keep distilling my closet!

  • Heather March 9, 2017 at 12:05 pm

    I loved a few of your winter dress looks, but I think you should just skip dresses and skirts in the winter if you’re not feeling it. There may be the occasional day when you want something different than the usual pants, which would be the perfect time to pull out a dress. I think it’s all about doing what makes you feel good!

    Also, I totally agree with Rebecca–leggings >tights under a dress!

    • Andrea March 12, 2017 at 11:07 pm

      Thanks for the feedback Heather – it’s a good reminder to stick to our instincts when it comes to clothing, and maybe not overthink it too much! ;)

  • Lindsey Kubly March 9, 2017 at 1:30 pm

    For me, this is the huge difference between capsules (variety and mixing is key) -‘and uniforms (repetition is key). More and more I’m leaning towards uniform dressing.

    • Andrea March 12, 2017 at 11:09 pm

      What a profound statement Lindsey – great point!!! Hmmm….. that really makes me think. Sometimes I miss dressing out the of the small feel of a capsule, but I agree, uniforms are appealing on an entirely different front.

  • monica March 9, 2017 at 1:53 pm

    it all boils down to smarter buying choices than i’m slowly learning to make. i have ‘should’ outfits days because i have ‘nice’ clothes in my wardrobe that are just there… waiting and i feel bad about having them and not wearing them… it feels like a waste…

    BUT sometimes i wear them in a different combination and then i fall in love with them again.. you go figure.. we’re so fickle…

    • Andrea March 12, 2017 at 11:14 pm

      Ha – so true on both counts! I agree, smarter choices is key, and I wish my learning curve was faster too. I *still* am finding some of my choices don’t pan out like I expected. AND sometimes I fall in love again too after a time. I guess the takeaway is to be also be slow and smart about what we subtract from our wardrobe.

  • Tawny March 9, 2017 at 3:15 pm

    I often think I ‘should’ wear dresses in the winter but I think I’ve finally accepted that I just don’t like tights and am overall too cold in dresses in the winters. I would still like to find a cozy cashmere dress I could wear with leggings to replace the thin sweater dress I have that I never wear. But even giving that a shot I think I’d stick to one winter dress.

    • Andrea March 12, 2017 at 11:15 pm

      A cashmere dress sounds like a dream! But wouldn’t it stick to your legs if you wore it with leggings? That’s the problem with winter, too many logistics to concern ourselves with.

      • Tawny March 13, 2017 at 7:16 am

        That’s a good point. Yeah way to many logistics and layers to deal with during winter, and one wrong item (like the wrong socks, aaahhh) and suddenly I’ll be cold the whole day. This is one of the reasons I hope to find a cashmere dress used since I’d hate to spend a ton on it then not really wear it!

  • Leah March 9, 2017 at 3:43 pm

    Yeah, I came to terms with the fact that I’m unhappy all day if I wear a skirt in cold weather. Too many layers to stay warm. I don’t like feeling constricted.

    • Andrea March 12, 2017 at 11:16 pm

      I wonder if a long-sleeved dress is the answer for us??

  • Paige March 9, 2017 at 6:33 pm

    I am definitely a ‘should’ dresser. That was a big push for me to make the jump to capsule wardrobes because I was skipping over my fave items because I felt I should try to wear everything in my closet. It’s much easier to avoid now, but I still sometimes wear things because they haven’t seen any love lately and I ‘should’.
    I try to wear dresses in winter, but I wait for the milder days. I always love your dress and denim layers!

    • Andrea March 12, 2017 at 11:17 pm

      I think if I had a job (like you, my smart friend) it would be easier for me to wear dresses. Sometimes it just feels silly for schlepping kids all over town. And thank you! Dress + denim = winning!! ><

  • MICHELLE March 9, 2017 at 8:30 pm

    I have a few “should” things left over. Two fancy formal dresses but they are tucked away in the drawer and some pieces that I love, except for the fabric. I may need to just cut them out soon. I agree that outfit isn’t your best. I keep wondering what it would look like if the denim were darker and just 2.5 inches shorter. I like that you are brave enough to post outfits that you aren’t too happy about. Perfection in the blog world feels so fake so this is refreshing.

    • Andrea March 12, 2017 at 11:18 pm

      Thank you Michelle for your honesty!! I really appreciate it! And I agree, perfection in the blog world feels fake, and it is also frustrating because it’s unattainable. Thank you for weighing in here! xo (And per the skirt, I think I need to just stop trying to make it work in the winter.)

  • Addie March 9, 2017 at 8:42 pm

    I appreciate your post today. I used to wear skirts and dresses in winter often when I lived in the SF Bay Area. But since moving to the East Coast, I have hardly choosen those items during the cold 6-months of the year. Although I love tights, skirts especially are much less appealing. This year though, I got an idea to sew up my favorite tunic dress in a Japanese brushed cotton fabric, with long sleeves and a slightly longer below-knee length: it was what I always wanted in a winter dress, comfy, warm, easily layered, and pretty. I still wear pants mostly but I am glad to welcome back a dress or two into my winter wardrobe. I say give the ‘shoulds’ a rest for a while and reevaluate later. It might help define what you are really needing instead.

    • Andrea March 12, 2017 at 11:20 pm

      Thanks for this comment Addie! I think that is excellent advice. You dress sounds amazing. I think a long-sleeved dress is a much smarter winter option that trying to deal with the logistics of a skirt. Some day maybe I’ll commit to one. I love that you made your own!!

  • Johanne March 9, 2017 at 10:56 pm

    I hear you 100% – just saw your outfit on Instagram, which I also think is so much more interesting.
    I sometimes think I should wear things that are traditionally flattering, but I usually don’t like them – more into oversize, weird shapes etc.
    Another one was skinny jeans in winter. Just didn’t feel right, however I know I’ll love them again come summer and sandals.

    • Andrea March 12, 2017 at 11:21 pm

      Isn’t that funny how our styles shift a bit? I’ll be curious to hear if you fall back into your skinny jeans in the summer. I find them too hot that time of year! But I wonder if your temps are milder?

  • Holly J March 10, 2017 at 6:17 pm

    Oh yeah! I know EXACTLY what you mean–I used to make myself wear skirts. For me, they are more effort (somehow, they are more effort…you have to be more ladylike in them! or something….:) ) and in the winter, they seem cold (even with cozy fleece tights….I was making myself wear them). I finally gave away most of my work skirts–they were so cute and beautiful, but I had to MAKE myself wear them. I have one or maybe two skirts per season now. At least I figured it out though! After…a while…lol.

    Great idea, asking yourself if you’d pack it for a trip! I never thought of that! Love your jodphur/chelsea boots!

    • Andrea March 12, 2017 at 11:23 pm

      Glad I could help on the asking yourself a question bit – that truly helps me!
      And I think I’m with you, I’m just not a skirt person, overall! Feels weird to say that because I love dresses. I only own a total of 3 skirts, one being pictured here. That’s a good reminder of something I probably don’t need to by. Thanks for the perspective Holly!

  • Lindsey March 11, 2017 at 7:54 am

    Oh my gosh, so I looked on Instagram at the outfit you love, and that Only Child Tunic looks amazing on you! Can I ask what size it is? As for the should – I do it all the time with pieces I spent “good money” on…pieces I have collected for some reason or another and don’t really like, but feel like I should wear. Some of those pieces I even get the most compliments on, but they just don’t feel like “me”. Part of my wardrobe / 2017 journey – blocking out the noise of what is “popular” and what I “should” wear. So what if I like all shades of navy blue all the time? One doesn’t need to diversify just because they “should”. Nothing wrong with the ole’ uniform. Thanks for being real, Andrea!

    • Andrea March 12, 2017 at 11:25 pm

      Ah, thanks so much for the great comment Lindsey! Your 2017 journey sounds very respectable, I hope you share more of it here!

      As for the Only Child Tunic – gosh, it’s a fabulous piece!!! I got the S/M, and it fits great. I’m 5’7″ and normally wear a size 6, or 28 in pants. I seriously want to wear the tunic every day. :)

      • Lindsey March 13, 2017 at 4:44 pm

        Thank you for the size info – so helpful! I can’t wait to see how you style it when the sun returns for longer than just yesterday 😀

        • Andrea March 13, 2017 at 9:21 pm

          You’re welcome! I hope you get it! And blech to today’s weather!!!!!