Shoes for fall?
September 27, 2015 6:25 AM   Subscribe

I need a new pair of shoes for fall, but I'm not quite sure what I'm looking for.

For years, I've gotten by wearing ballet-type flats most of the time and then big heavy winter boots when it's too cold for the ballet flats. However, what I'm missing are the in-between shoes: shoes that can be worn with socks, that will keep my feet warm, but aren't enormous snow boots.

- Must look good (or not-horrible) with socks
- Have good cushioning and some arch support (I will be traveling a lot in these and just generally walking a lot and I have low arches).
- Ideally costing under $100, will stretch to $150 if necessary.

The big problem I'm having is that there are several kinds of shoes that fit these criteria that I don't like for one reason or another:

- Riding boots: I have a pair of these but I don't feel they're super-flattering on me.
- Clogs: the ones that are built for comfort all seem frumpy to me.
- Oxfords: The women I've seen who pull these off either have a very polished preppy look going on or more of an eclectic "90s throwback" look. My look is more "jeans and cardigans" and I don't see that going well with oxfords, though I'm willing to be persuaded!
- Booties: I really hate these for some reason! Sorry.

I've seen some short lace-up boots that I like and will try out. What else should I be looking at? I'm looking for either general style recommendations OR specific products/brands (especially if they are known for comfort).
posted by lunasol to Clothing, Beauty, & Fashion (15 answers total) 17 users marked this as a favorite
Some general recommendations: Clarks, Sofft, Trotters and New Balance are brands I like. I shop at Nordstrom's, DSW, Ebay, and Joe's New Balance Outlet. I do a lot of online shopping because I have peasant feet that need wide width shoes, but if you wear between 7 and 9 medium, you should have a decent selection in brick and mortar stores as well.
posted by Rosie M. Banks at 6:54 AM on September 27, 2015 [1 favorite]

I'm a big fan of the short lace up boots that go above your ankle but not up to your calf (as opposed to booties which go below your ankle bones). Last winter I got a pair of Lucky lace up boots that I love the look of, and I think they're comfortable. They aren't the absolute most comfortable shoe ever, but I have very sensitive problem feet, so I can't even wear most shoes. The ones I have are in the bottom right hand corner of this picture. (I couldn't find an actual link to them, but that picture also gives you an idea of some other lace up boot styles.)

I also have a black pair of Steve Madden lace up boots that go up a tiny bit higher than the Lucky's. I believe it's these ones.

For a slightly more casual look, I also have these sneakers (in black) by Ecco. They're quite comfortable, and they have a removable sole if you want to use an orthotic.

Oh, all of these shoes should be in the $100-$150 range, maybe less depending on sales, etc.

In terms of brands, I've found Born shoes to be the most comfortable brand for me, but I tend to prefer their tall boots (and ballet flats). I haven't found a fall shoe that I'm a fan of from them, though. Clark's are another brand that are known to be comfortable, but I haven't found a shoe by them that I like the style of.

I'm also a jeans and cardigan kind of person for every day wear, fwiw.
posted by litera scripta manet at 7:01 AM on September 27, 2015

One other thing: Zappos as a category called "comfort" that may give you some ideas to sort through. In general, Zappos has a good selection, and a great return policy, but they tend not to have very many sales.
posted by litera scripta manet at 7:04 AM on September 27, 2015

I usually go with a "bootie" sort of like this. There are many more styles in that same page.
posted by CrazyLemonade at 7:05 AM on September 27, 2015

Re: Oxfords and being convinced - I don't know that you have to go polished/preppy or 90's throw back, but I do think they look the most stylish with straight leg trousers or jeans. Even the looser boyfriend style jeans that are rolled/cuffed at the end can look great with oxfords.

Do you tend to wear straight leg/skinny style pants? It may sound a bit duh but I feel it's worth pointing out that the style of pants (or dress/skirts) you wear most often should be taken into consideration, so that your shoes pair well and you feel 'right' in them.

Like you, I tend to be either in ballet flats or boots, but I have found that oxfords (with or without dress socks, styled appropriately) are the best shoes for me in the fall because they can be casual as well as workplace appropriate.

However, I would argue that wedge style heels are the next best alternative. They cover the foot more than a ballet flat, they're easier (and arguably more comfortable) to walk in than high heels, and they also do well as day to night shoes. I think they're also more versatile and easier to style. I do think you could wear them with a quality pair of dress socks.
posted by nightrecordings at 7:20 AM on September 27, 2015

I've had the same issue myself! I've been wearing lace up boots (UGG Kesey boots, which are not the typical UGG boots and are on the heavy/warm side), Keds-style sneakers with no-show socks (Grasshoppers actually, which have padding and some arch support, unlike Keds), and .... booties?

You say you hate booties but you don't say why? Or what exactly you consider a bootie. Is it the popular look with skirts/dresses and skinny pants you hate, or do you find them uncomfortable? I'm personally not a fan of the look with skirts and skinny pants on me, but I do find I like them under bootcut pants! I like chelsea style boots, like Bogs Kristina and Trotters Leah boots. Not sure if you consider those booties so I thought I'd throw those out there :)
posted by geeky at 7:57 AM on September 27, 2015

Ankle boots are probably what you're looking for. Sounds like you're digging the lace-up boots (you can find more by searching "combat boots"). "Chelsea boots" are back in a big way right now. "Moto boots" are my personal favorite in the ankle-high category -- I find them very comfortable and versatile, and the ones with the more almond-shaped toes look good both with jeans and with skirts + leggings. Here are some examples.
posted by ourobouros at 8:11 AM on September 27, 2015

Seconding Chelsea boots! Great with any style of jeans, classic, and apparently on trend now? Plus, they're super comfy and different brands do slightly different takes on the style, so you can find a shape/color/look that suits you.
posted by Meg_Murry at 8:19 AM on September 27, 2015 [1 favorite]

Soft oxfords? Would look great with jeans and cardigans.
posted by ellieBOA at 9:17 AM on September 27, 2015

I have two pairs of Cobb Hill's Sheila. They're incredibly comfortable (even for someone not usually wearing heels). Might be too preppy and probably looks better with trouser socks rather than "heavy" socks. But so comfortable!! And they look fantastic with jeans!!
posted by yonglin at 9:52 AM on September 27, 2015 [2 favorites]

I'm a big fan of any loafer, particularly with a sweater + jeans look (like this).
Also, don't count out sneakers -- they are everywhere right now and can definitely look chic like so. Plus they're comfortable and inexpensive.
posted by thebots at 10:19 AM on September 27, 2015 [1 favorite]

Response by poster: nightrecordings: good question - I wear straight-legged/skinny jeans, usually in dark-wash or black.

geeky: I don't have any particular reason for hating them, just not my style.

thebots: I like loafers too, but I feel like you have to do socks with them juuuuust right for it to work.

Everyone: thanks for all the great recs so far. I'm on my way to being convinced about oxfords, and loving all the lace-up boots!
posted by lunasol at 11:38 AM on September 27, 2015

Cobb Hill Petra is my recommendation; I've worn some variant of these Mary Janes for several years, since I first set up a standing desk. They look great with or without socks. Check out the rest of the Cobb Hill line for other cushy and supportive but good-looking options.
posted by limeonaire at 11:40 AM on September 27, 2015

My fall/winter uniform is straight leg jeans with cardigans with my Frye Carson oxfords. Super comfortable and I've gotten lots of compliments.
posted by gatorae at 11:58 AM on September 27, 2015

I forgot to add, the Fryes go on crazy sales all the time, so don't be put off by the $250 retail price. I regularly see them on sale for under $150 if you are willing to pricewatch a bit.
posted by gatorae at 12:07 PM on September 27, 2015

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