Posts Categorized: shoes

Reader Request: Styling Flares

how to style flare jeans

left | right

Reader Sarah emailed me this question:

I wondered if you could do a post or a question in your column or something on styling flares. I love that flares are back in style (great for balancing hips), but I am having trouble with the silhouette. Fitted on top or not? Long or cropped tops?, etc. Also, what shoes?

Oh flares, my old friends. I wore you throughout college, and well after … even when the rest of the world had switched to skinnies. And now I can’t quite believe you’re back. Already. Although, in my mind, 1990 is only 10 years ago

ANYWAY. Flares are the silhouette of the season, and I imagine Sarah isn’t the only one who’s thrilled to see them on the racks once more. But they are a bit of an exaggerated silhouette, so they can feel challenging to style. Here are my tips:

Hem them

It’s always a good idea to have your pants and jeans hemmed for the style and height of footwear you intend to wear with them, but it’s especially important for flares. There’s a lot of fabric down there by your feet, and cultivating a ragged, dirty hem will only distract from your overall look. If you are long-waisted and short-legged, consider seeking petite flares since hacking off more than a couple of inches may affect the flare silhouette and balance of the jean. (It’s true that some folks are wearing cropped flares, but that trend is still on the fringes. And not terribly practical for cold weather.)

To avoid the no-feet look, consider having your flares hemmed slightly higher in front. And remember that pants hemmed for heels shouldn’t be worn with flats and vice versa. Speaking of shoes …

Try heels

You certainly can do flats with flares, but to my eye a heel makes the silhouette more fluid and graceful. Even a small heel, platform, or a wedge will work – something to give you a little boost of height and elongate your legs. Flares only make your legs look long and your silhouette look hourglass-y if there’s some distance between your hips and the flared hem. Heels can help. It’s a matter of preference, of course, but my preference is for heels with this cut.

Short or fitted tops

Flares can be worn with loose or boxy tops and jackets, but opting for something that shows at least half of your hip height and is somewhat fitted reduces the risk of swamping your figure. This is especially true if you want to wear flares either to elongate your leg line (a shorter top will do this) or create balanced curves (a fitted top will do this). For length, think three or four fingers’ width above your crotch point. And if you’re not too keen on clingy tops, try a fitted top in a relatively heavy material like ponte or a mid-weight sweater then add a looser jacket on top.

Or blouses … though consider tucking

Button-fronts and blouses are a great way to dress up your flares. In fact, some fashion experts and editors advise against going too casual with your flares-based looks to avoid an overly 90s feel. Since many blouses add volume, try tucking or half-tucking with your flares. It’s another great way to elongate your legs and keep the silhouette tidy, and allows you to add a belt to your look. You can also do a loose, floaty blouse and then bring in the float with a fitted, structured jacket.

Avoid tunics

What makes flares flares is the out-in-out shape they create on your body. A tunic-length top will cover most of your thighs, and unless you’ve got a pair of super-fitted flares that cling to your knees, that tunic top will obscure the curve inward from your hips to knees. Even if you opt for a longish top, make sure it tops above the crotch point so you can reap maximum curve benefit. Or if you want to play with proportion and use a longer line up top, try a fitted underlayer and longer jacket or duster.

As always, none of my figure flattery advice posts should be considered gospel, including this one, and I fully expect you to read them with a grain of salt. Style “rules” are merely guidelines, no matter who is dispensing them. I trust you to use your judgment. And I trust you to take what applies to you, discard the rest, and assume positive intent.

Hope this helps! And have fun flaring it up this season!

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details. Sustainable options are either used, handmade, made in the U.S., artisan made in non-sweatshop conditions, or made using sustainable/fair trade practices.

Related Posts

This Week I Love …

Freebird by Steven.

So Steve Madden, right? I remember the 90s and how having a pair of his shoes was a BIG DEAL back then. (At least to teenagers such as myself.) And then the brand shifted out of favor for a while, and now it’s just a mainstream, accessible, solid brand. (My most worn pair of shoes is by Steve Madden.)

But Freebird by Steven – a newish offshoot of the parent brand – is a different story. For one thing, it’s WAY more expensive, so always poke around Amazon and eBay before pulling the trigger. But for another, the designs are edgy and tough, made from gorgeously distressed leathers, and adorned with subtle details and creative hardware. I am so very smitten with this brand.

Here are a few pairs you can nab right now:


Bolo, $275

I used some magical combination of coupons and got these from Amazon for around half off a month or so ago. (They’re cheaper there now, too, and 6pm has a few pairs at half off.) They are even more gorgeous in person, though that 3″ wood block heel isn’t exactly the comfiest. Still can’t wait to pair them with dresses or tees and jeans for summer. Also love the similar Hustle style.

freebird dakota boot

Dakota, $166.21 – $231.90

Love the detailing on this boot, from the wrapped strap to the x-stitched front panel to the back zipper. These also come in black or tan, but this dusty gray will be fantastic for spring and summer wear.

freebird sandals

Wing, $195

Some of the sandal styles are a little too clunky for my taste, but this strappy heel is stunning. More on the casual end of the spectrum so perhaps not ideal for dressy nights out, but perfect for edgy warm-weather looks. More sizes and black version at Bloomingdale’s.


Boulder, $285

I’ve sworn off mid-calf engineer boots, but the combination of medium height and chunky heel on this boot intrigues me. This rich tan is another versatile spring/summer shade for boots, but the Boulder also comes in stone, a dark red-brown, and weathered black.

freebird by steven coal

Coal, $350

So much money, but SO AMAZING. This pair is quite tall at 17″, but would be equally amazing with Boho and rocker chic looks. Fold over the top of the boot shaft to mix it up. This burnished cognac is breathtaking, but these also come in black.

freebird phoenix

Phoenix Low, $275

I know the crusty, weathered, post-apocalyptic look isn’t for everyone, but it gets me every time. And that distressed finish has just a hint of metallic sparkle to it. SWOON. The tan and gray suede versions of this low boot have smoother finishes.

Other sources to check include Nordstrom Rack,, Nordstrom, Shopbop,, Onlineshoes, and Zappos some of which carry exclusive or past-season styles.

Anyone else tracking Freebird by Steven? Thoughts on the styles?

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details.

Related Posts

Reader Request: Shoe Alterations

getting shoes altered

Hayley popped this question into the suggestion box:

I’d be interested in knowing if you’ve ever had any pair of shoes altered in any way, and if you have any tips. I’m considering getting a pair of leather boots taken in a bit at the top around the calf area.

Why yes, I have! Here in the Twin Cities we have two leather shops both owned by various members of the George family – George’s Hockey Repair in St. Paul, and George’s Shoes & Repair in Arden Hills. The latter is now my go-to – and the shop that helped with my fringe bag – since they do great work and aren’t as mobbed as the St. Paul shop. But I’ve had one pair altered at each shop. This first pair was done at the St. Paul shop.

tall boots shortened

These olive green Coclico boots were just a couple of inches taller than I’d have liked. The photos aren’t the greatest, but you can see how much more real estate that zipper takes up on the right (post-alteration) than it does on the left. And speaking of that zipper, its length and placement made these boots ideal for shortening: Since it doesn’t run the length of the boot, the zipper itself didn’t need to be lopped off at all.

boot alteration

Here you can see that the boot is lined with a different color/texture of leather. The original finish was fancy, with rolled edges on both liner and outer. I was happy to have a slightly raw-er finish for the alteration since very few people get super close-up to my feet. I believe this alteration cost about $30. These boots have been languishing in the closet for ages now, but I’m not quite ready to part with them now that I’ve shifted to a more neutral, subdued palette. We shall see.

mmm work mocs

These are a pair of Maison Martin Margiela Work Mocs that I stalked on eBay for YEARS and finally nabbed for a fraction of retail. When I ordered them they were tan. I swear they were more of a yellow tan than this, but I never remember to do “before” photos, so who knows?

work moc brown

I got them, drooled on them, and then spent several hours trying to build an outfit around them. And that’s when I remembered that tan shoes really, really don’t work for me. (Unless they are sandals. And these are definitely not sandals.) So I took them out to Arden Hills and asked if they could be dyed black. This shoe style was actually made in black, but the pair I found in my size and price range was tan and I was so excited that I bid before really considering the color. And, as it turns out, dyeing them was fairly straightforward.

can you dye leather shoes

But imperfect. I wanted the interior black, too, but with that raw, unfinished leather the experts told me I’d just end up with black dye rubbing off on my socks. And I was warned that the dye process was messy and some might end up on the soles. It did. No big, in my opinion. This alteration cost $45.

And these shoes, too, haven’t gotten much love. That heel is chunky but feels incredibly high, and I’m still tinkering with the proportions of these booties. And honestly? I’m starting to find that although I can generally get clothes and accessories altered more or less to my personal specifications, many of the ones that need drastic changes end up going unworn. Aside from a few simple shortened hems, I’ve ended up donating an awful lot of things that I’ve bought and had altered. Which isn’t to say that YOU will be the same way. Just something I’ve noticed about myself and am still mulling.

Now. In terms of having a tall boot taken in at the calf? It is possible, especially if you have a relationship with a truly skilled leather worker, but it will be costly and potentially imperfect-looking. I’ve asked for this specific change on several pairs of boots and been told they’ll look quite odd afterwards. I’ve also had leather workers just refuse to even attempt it. Curious to know if any of you have had tall boots slimmed in the calf. I imagine it will be easier on styles with lots of built-in seaming.

I also know that, in some cases, heels can be slightly shortened by a shoe repairperson. You can’t turn towering stilettos into kitten heels, but you might be able to make a 2″ heel into a 1.75″ heel.

Most of the rest fall under “maintenance and repair,” in my mind. Heel tips, resoling, replacement of buckles or eyelets, getting shoes stretched to fit, reinforcing worn-out bits of leather. But I’m sure there are things I haven’t even dreamed were possible! Have any of you gotten shoes altered in significant ways? How did they look in the end? Was it costly? What would you recommend and warn against?

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details.

Related Posts