AMA: The Fall Boot Edit
Let's keep those toesies warm.
Hi Jess! I’m in desperate need of boots. Budget isn’t my issue, I work hard and can afford to buy what I want. But when I get on these big websites like Net-a-Porter with a million options, I get decision paralysis. Could you do a boot roundup with some styles you recommend? I live in New York and it’s getting too cold to get away with my commuter sneakers much longer. I see all the cool girls walking around with boots that zip up the front and feel frustrated that I don’t even know where to look online for the stuff I want. Shoe shopping at the department stores is just too stressful here. I want to invest in two or three really nice pairs that I can have for a long time that are high-quality enough that with good care, I won’t have to think about this again for a few winters. I’m overwhelmed! Sorry for the long message! I’m a premium subscriber and I opted in to be able to ask you questions like this. Thanks! - Sarah, via IG DM
Hi Sarah!
First of all, congrats on being a boss-ass bitch! We love to see a girlie thrive and get her monies. Second of all, thank you for being a premium subscriber! This is a great back-to-basics question that I think lots of people struggle with. It’s very brass tacks. The moment when you need to buy something for practicality’s sake: you know you’re going to have to sink some money into it, but you have no idea where to start and don’t want to waste your coins on something that you end up hating.
And I totally feel you, I get overwhelmed shopping online too! How can you not when there are 20+ pages in any single category?
MyTheresa is (as y’all may know) my favorite sweet spot for fashion procurement. They ship quickly, they have a new, streamlined return process that’s a breeze, and their buy is unmatched. The edit’s sort of already been done for you. I always find something killer that everyone asks me about (right now, that’s this delightfully fuzzy sweater and this luxe-feeling coat).
Plus, isn’t it so nice to try things on at home, with your own stuff?
Boot Fit Tips:
When you’re boot shopping, the fit is so important. This isn’t really the moment you can fudge a half-size for vanity’s sake. Check the toe box — is your big toe too close? Try a half-size-up. And make sure the boot flexes where your foot naturally bends, otherwise, it’s going to rub
It’s worth it to order several sizes of the styles you like. If you work with a personal shopper, usually they will ship your items on consignment so you only have to pay for what you keep.
Try your boots on near the end of your day! Your foot swells a bit as the day goes by. A boot that feels good on your morning foot could feel uncomfortable by EOD.
An everyday boot is a hard-working shoe in a city like New York (or anywhere cold, honestly), so make sure above all, it’s comfortable and stable. The runway trend of death spiral shoes is to be ignored as seriously as this season’s thin eyebrows!
When your order arrives, try on your boots with the socks you intend to wear with them. You’ll want to make sure they aren’t too tight with that extra layer.
If it’s a knee-high style, make sure they pull up over the pants you’d like to wear with them if that’s a look you want.
Make sure the heel height works with your favorite pants and jeans, too. You don’t want the back of your favorite trousers dragging on those soggy, salty sidewalks.
It’s okay if they feel stiff at first! Most nice leather does right out of the box. Give yourself time to break them in.
Caring for boots is simple. If they’re leather, condition them every so often with a bit of mink oil. In the summer when you’re not using them, take them to your cobbler if repairs need to be made, and stay on top of re-soling them every few years.
So what are we buying, then?
A classic riding boot is a super safe bet here, and they’ve re-entered the fashion conversation after a few quiet years, so jump on that lack of dormancy and invest now while there’s a good selection to be had this season. I own these by Toteme — they are my most-worn boot. I also think these Prozenas are absolutely timeless.
You can have a little more fun with dressier styles. Given New York is such a walking city, I’d still opt for a lower heel for most situations (this other Toteme pair checks that box perfectly), but investing in one sexy higher pair (with a wedge, even! or at the very least, a sturdy heel!) for those curb-to-cab nights is worth it as well.
If you want to mash up a variety of needs — a little heel, a goes-with-most-things color, a style that looks great under or over pants — opt for these by Khaite. She makes them every single season, they aren’t going out of style anytime soon.
As for those boots with the zippers you’re referring to — the ones that all the cool girls are wearing? They’re by The Row, and they’re an enduring style. Trendsetters like Zoe Kravitz and Hailey Bieber are spotted in them perenially. That elevated rubber sole makes them a really good option for the city — practical and comfy, but still gives you a little height boost! They look great under denim and trousers, with a skirt, or over a legging. And they come in a variety of materials and colorways (yes of course black! brown!), so you can find something that works with your closet.
In the same vein, these by Loewe are a more classic Chelsea style, but equally as appealing. Or if you want something that you can pull up over your leg, maybe this style by The Row instead.
Any of the aforementioned styles will be with you for many, many years. They’re well-made enough that I’d venture to say you’ll tire of them before they’ll tire of you. Boots like this don’t really give out.
Hope this helps in your shopping endeavors. As always, I’m here to help!