Shopping Help: Basic Shoes 101

I can’t keep track anymore of how many people have asked me for help with shoes over the last few years.  The two main questions are, “What are comfy shoes I could wear that are not heels but are not sneakers?” and the more frequent question which goes something like, “I need help with shoes!  I have no idea what to do with them or where to start!”  So, not really a question, but a general plea for help.
I haven’t really know how to help with the latter because I don’t have clarity on what’s confusing for those in need of help.  While I love a pop of color in my shoes, at least 75% of the time I’m wearing cognac/tan shoes.  My advice would simply be to start there.
Otherwise I’ve rounded up a few types of shoes that are basic building blocks to start with.  All from Old Navy and Target.  If you need shoes that have more padding or cushioning you should still be able to find similar styles at stores with more expensive shoes since these are all pretty basic.

Simple Heels:  Option 1  |  Option 2  |  Option 3
Most basic options for workwear OR for going out and special occasions.  I own pair #1, and there’s a small platform in the toe box which makes them a lot more comfortable than a normal pump–the heel doesn’t feel so high and doesn’t put as much weight on your toes.

Options 2 and 3 are classic, sleek styles.  Instead of having that shiny, patent leather look, these look more like suede, which I personally love for pumps.  Something about the matte look works well for office type looks but also works really well with jeans without me feeling too dressy or fancy.

I love #3 and am considering ordering them but I’m waiting to see how my feet are after birth until I buy anymore shoes!  I LOOOOVE that color though!

NOTE: These all come in black and other colors, even some leopard and snakeskin prints.

Solid Flats:  Option 4  |  Option 5  |  Option 6
This group addresses shoes that aren’t heels or sneakers.  Any type of ballet flat is the easiest place to start if shoes confuse you.  I own #4 and wear them as my go-to shoe.  When all else fails, when I have to walk around a lot, when I don’t want to think about shoes, I step into these and head out the door.  (See them in action here.)

There are also pointy toed flats like #5 and #6 that can elongate your leg line, whether you’re wearing jeans of any cut, straight legged slacks for work, or a skirt.  Great alternative to a heel!

NOTE: All come in different colors.

Flats with Details:  Option 7  |  Option 8  |  Option 9
Finally, flats that are neutrals and still somewhat basics but offer a little more than a plain flat.  Details like quilted textures or small bow ties give more interest to the shoes without being anywhere near too much.

NOTE: All come in different colors.  Option 6 comes in a two-toned white with black cap toe, kind of like Option 9 but with the quilted detail.

What’s your favorite basic type of shoe?  (Like the tan flats for me!)

Also, if you have specific shoe questions please leave them in the comments.  I would love to help the people who’ve asked for shoe help, but I really need more clarity on what is confusing.  The more specific the questions the more helpful I can be.

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  • Reply
    August 15, 2014 at 7:52 pm

    I am one of the people that follow your outfits verbatim… when you have on tan flats in the picture i wear my tan flats as well. Could you show some of the outfits you have worn with tan flats with other shoes. I LOVE wedges as well but find that sometimes the outfit doesn't come together the same if you finish it off with wedges instead of flats.

  • Reply
    Sabrina Nooruddin
    August 15, 2014 at 8:31 pm

    #6 is my favorite, I love those styled black flats!

    x. Sabrina | Simply Sabrina

  • Reply
    Domesticated Working Woman
    August 15, 2014 at 8:50 pm

    I'm a flats girl. I would also recommend TOMs to anyone who is looking for cute shoes that aren't sneakers and aren't necessarily workwear.

  • Reply
    August 15, 2014 at 9:21 pm

    These are all super cute options. The problem I have with flats, though, is that when it gets even a little chilly (say, in an air conditioned work space), I want to wear socks. Just normal socks, not special tiny socks I have to set aside to wear with flats. Do you have suggestions for non-athletic shoes that can be worn with normal socks that would still look cute with a skinny pants outfit without looking clunky?

    • Reply
      August 15, 2014 at 9:34 pm

      what about brogue? They are HUGE now, can be worn with socks, and look great with skinny pants, skirts, etc

  • Reply
    August 15, 2014 at 9:23 pm

    I recommend genuine leather for people who don't know where to go with shoes. It tends to break in better (more comfy, less blisters) and last longer than synthetic materials. It took me many years and countless band-aids to figure this out. Nine West is a great for affordable leather flats and I often find them at discount stores like Marshals.

  • Reply
    August 15, 2014 at 9:32 pm

    I love these options, but wanted to give out a shout for 6pm. My feet can't handle from target or Old Navy anymore, and I have found fantastic shoes from 6pm at a fraction of their usual price. I got Cole Hana nude heels for $50, their ballet flats for $30, etc. Cole Hana is normally out of my price range at other retailers, so it's been awesome! I look stylish AND my feet are comfy.

  • Reply
    August 15, 2014 at 10:55 pm

    I have a maryjane addiction. Are those even remotely instyle or is it just me wearing them these days?

  • Reply
    Rachael K
    August 16, 2014 at 1:00 am

    oxfords and mules are a totally overlooked basic shoe style. I think they're more versatile than people give them credit for, and also a bit unexpected… and still classy!

  • Reply
    August 16, 2014 at 1:29 am

    I am definitely gonna be checking out number 6 at my local Old Navy soon. Those are so cute! I hope they are comfy.

  • Reply
    August 16, 2014 at 1:35 am

    omg #7!!!!!!!!

  • Reply
    Jeanne Brunner
    August 16, 2014 at 2:34 am

    Payless has absolutely amazingly comfortable heels. They're the Karmen Comfort Plus. I danced in them all night long with no problem because they have such great cushioning! I own the black and nude.

  • Reply
    August 16, 2014 at 4:02 am

    I'm someone who has asked about shoes. I have no idea what to wear with a skirt besides sandals. Basically I wear various sneakers (sports or casual) and either chaco or mephisto sandals. This mostly because I have foot issues; I have to wear orthotics or a footbed with arch support, or I end up with painful tingly feet, or pain in my big toe joint. I couldn't wear any of the shoes above because the soles are too thin. There's lots of fun, more "substantial" flats out there (I love Camper!) but I have no idea how to wear them. Basically cheap shoes aren't an option for me- I invest in a few more expensive ones that keep the feet happy. I just wish they weren't all sneakery!

  • Reply
    August 16, 2014 at 4:14 am

    You can get Dr. Scholl's inserts (or another brand) that have arch support. Dr. S calls them orthotics. I've used them and they've helped with arch and heel pain. If you get hip pain, you could also check out the stretches and strengthening exercises in Runner's World. I just had physio for hip pain caused by a muscle imbalance- stretch & strength really worked. Runner's World has a "Where does it hurt?" section which can help you figure out what the problem might be, how to fix it and when to see your MD. Don't let it go. Joint pain often get worse, and the longer it goes on the harder it can be to treat.

  • Reply
    August 16, 2014 at 10:56 am

    I can't wear anything slip-on as I have narrow heels and they wreck the back of my heels. I also have short legs so mary-jane style or ankle straps look terrible! I wear boots with a wedge or low chunky heel in winter (I walk a lot, so need comfortable). Any suggestions for summer options that might work? Thanks!

  • Reply
    Reggie Moon
    August 16, 2014 at 12:41 pm

    I can't wear Target or Old Navy shoes because I work on my feet for nine hours and they just don't cut it. Wow they're cute though! Me Too, Merrel, and Birkenstock are the brands I have the most luck with. I try to find them discounted at DSW, Marshalls or TJMaxx.

  • Reply
    August 16, 2014 at 2:10 pm

    I have weak arches, long narrow feet and I'm prone to blistering. I swear by my Easy Spirit heels. I also like Clarks brand, they also sell cute flats. A lot of the "comfort" brands are starting to put out nicer shoes that don't look like something your great-grandmother would wear.

    That and I've stopped buying cheap Target or Old Navy shoes. It's just not worth the pain and at 29, I'd like to avoid having bunions like my mom and my sisters.

  • Reply
    Ireland Headrick
    August 16, 2014 at 2:57 pm

    My favorite basic type of shoe… hmm, for now I'm going to have to go with Chucks. I'm a high school student, so there's no need for me to own "professional" shoes, but I do love a fun pair of heels. Every couple months or so I find a great pair secondhand. One of my favorite ways to shop!

    Please check out my blog if you're so inclined: Ireland Rhea

  • Reply
    August 16, 2014 at 6:36 pm

    I have a few pairs of flared-leg pants (not bellbottoms, just flared). They're really too short to wear boots, and since I'm a teacher I'd rather not wear heels all day at work anyway. Any suggestions? I do have a suede "driving moccasin" type shoe, but is it a faux pas to show a little foot skin between the pants and where the shoe starts?? haha
    Flats just don't seem to look right with a flared leg. (Or maybe flared leg pants are totally out and I should get rid of them?? :/ )

    • Reply
      Miss Hot Couture
      August 16, 2014 at 10:00 pm

      Hi Kristen and Audrey – I hope this is not rude to reply but I used to have the same dilemma like Kristen with the flared pants and not wearing heels. I hope you don't mind me sharing my two cents, but I used to wear heels with the tiniest wedge, like 1.4 to 1/2 an inch so it was super comfy and I could walk all over the place with them. This would work really well if the pants are hemmed at the right length so the shoes would not drag on the floor and ruin your slacks. However, now I just wear ankle length skinny pants. 🙂 Hope this helps!

  • Reply
    August 16, 2014 at 8:23 pm

    Happy due date girl!!! So excited to see when she makes her debut into the world. Eden started coming at 3am on my due date, so basically right on time. So happy for you and B! Love all these flats, they're my favorite! -♥- Rachel (For the Birds)

  • Reply
    Rebekah Daphne
    August 17, 2014 at 12:33 am

    I want one of these so much 🙂 and you look adorable!

  • Reply
    August 17, 2014 at 2:02 am

    I have the same preference.
    I am super in love with oxfords for this purpose. I just picked up a pair of these, for example:

  • Reply
    August 17, 2014 at 3:25 am

    Wow! That's a fan-freaking-tastic diaper bag! I'd love to own one. What a gorgeous color…

  • Reply
    Lauren @ Exploring My Style
    August 17, 2014 at 4:52 am

    Yes, flats and sandals are my go-to for sure. I am SUPER picky about my shoes so unless they are comfy from day one and have plenty of padding, I don't even bother. Ain't nobody got time for angry feet! I tried on a pair exactly like your cognac ones from Lucky Brand that are super comfy and will be getting as soon as I can find them on sale. I am having the hardest time finding the perfect pair of leopard flats though!

  • Reply
    August 17, 2014 at 5:33 am

    I'm not sure what you need shoes to go with (are you a stay-at-home mom? work in an office? college student?), but two general recommendations.
    Ankle boots, or booties, are surprisingly versatile and should have plenty of room to accommodate the top of your foot. Two cute options: and, and honestly searching "ankle boots" or "ankle booties" should get you some results at pretty much any big store. 🙂
    If you need something a little more office-appropriate, there's a type of flat called a "d'Orsay flat" that's shaped a little different and might be more comfortable for your foot type. Like so: or Hope this helps!

  • Reply
    August 17, 2014 at 3:42 pm

    I can't wear skinny jeans, most of my bottoms are bootcut or straight. What type of flats do I wear them with and still look stylish?

  • Reply
    Laurie Bolduc-Cadieux
    August 17, 2014 at 11:10 pm

    What an amazing bag! You look beautiful!! Best wishes when the big day arrives! To health and happiness!

  • Reply
    August 18, 2014 at 1:47 pm

    Those are cute! Oxfords never even occurred to me because I always thought they were…what's the word? Costumey? Or maybe I'm thinking of saddle shoes. In any case, the ones you linked are nice and really would go with anything! Thanks for the tip!

  • Reply
    August 21, 2014 at 8:23 pm

    First I have to say that I love your blog and I love that your style is so accessible:)
    One question about shoes is during the winter especially when it is snowing I always am not sure what shoes to wear under my flared or not so skinny jeans.

  • Reply
    August 25, 2014 at 3:12 pm

    How will you announce the winner of this contest?

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