Wearing dresses with slouch boots

September 29th, 2009

Eighties inspired slouch boots make my “must haves” list for the season because they’re a simple way to update your existing Autumn and Winter wardrobe. They’re available in all sorts of vibes: heeled, flat, platform, ankle, mid-calf, knee-high, cowboy, biker, bedazzled, distressed, suede, canvas, plastic and leather. You name it and you’ll find it.

At first, you might not fancy the slouchy volume around the calf and ankle, but it has its advantages. It tends to balance out ensemble proportions so that you don’t look like you’re going to topple over (boot cut pants achieve a similar sense of proportion with their wider hem). Slouch boots are often easier to fit than regular knee-high boots because they don’t need to fit precisely around the calf area. They can either gape on narrow calves, of fit snugly under a wider calf. And slouch boots do a great job of dressing down a dressy outfit.

You can wear slouch boots over skinnies and cigarette pants, with skirts and shorts, or under dresses. Paired with shorter frocks, with or without hose, is my favourite way of wearing them at the moment because the outfit transitions into Autumn so perfectly, especially if your weather is mild.

Pinstripe PinaforeOmbre SheathWaterfall Sheath
Click pictures to enlarge

It’s important to raise the hemline of the skirt or dress with slouch boots. Somehow the proportions are off when the hemline finishes on or below the knee making you look dumpy and short-legged. Wearing my frocks this short is one of the ways I’ve evolved my style this season. I haven’t exposed my knee caps and the top part of my thighs for fifteen years! But the boots provide extra coverage and hose helps too.

I’ve paired the look with sleeveless dresses because that’s my style preference, but most frocks and skirts will work with slouch boots as long as the hemline is shorter. I add a boyfriend jacket, cascading cardigan, biker jacket, denim jacket or boxy Chanel-esque jacket on top when it’s chilly, and peel off that layer when it’s warm. You don’t have to stick to heeled styles with this look either. Both my grey and black boots are flat because I also love to wear frocks with flats.

Remember that you can substitute dress and slouch boot styles that are more to your taste to make this look work for you. Lasses of all ages and sizes are wearing this combination in downtown Seattle recently and it’s fun to see different takes on the same outfit formula. So do you think you’ll wear frocks with slouch boots?



54 Replies

Posted on Tuesday, September 29th, 2009 at 7:39 am

I sort of doubt it, since I absolutely do not have the legs/confidence to wear shorter-length skirts. I have one pair of sloutch boots that finish a few inches above the ankle, and I may experiment with tucking (with forum guidance, of course), but I suspect that’s as far as I can go with this trend.

Posted on September 29th, 2009 at 7:43 am

I love this trend and will be wearing it through out the season. I have switched to wearing tights already due to the recent drop in temperature in the UK. Permission to steal the last look Angie?

Posted on September 29th, 2009 at 7:46 am

Thank you so much for this article Angie! I love when you model for us, these are my favorite posts! You look amazing in this look! I love the apricot earls and envy your ability to wear drop-waist dresses, like the gorgeous first grey one.
I have tried this combo for the first time last weekend and loved it. I will be wearing it more, as long as the weather permits it.

Posted on September 29th, 2009 at 7:46 am
Phoebe

You look great in these frocks. Especially the first one is yummy. I like the boots (with a hose, of course;) very much. The higher ones are elegant and trendy. <although I usually stay away from mid-calf boots (proportion!), these look fine to me. And they must be very comfortable. Definitely on my shopping list!!

Posted on September 29th, 2009 at 7:49 am

I like this look on you, Angie. I want to like it for me too, but I have a hard time wrapping my brain around shorter skirts and shorter boots on my tree trunk legs. I tried shorter boots a few weeks ago, and didn’t love it. Even my regular “dress” boots from last season are shorter (hit right at mid calf) and I wore it with a shorter dress and black tights and it didn’t look good.
I’ll keep trying as always, but I’m not convinced it’s the best look for me.

Posted on September 29th, 2009 at 8:04 am

I love the look. The only thing that would hold me back from the look is my budget. This would require the addition of both new boots and new dresses. We shall see.

Angie, explain to me how the first boots qualify as slouchy. I definitely get the other two.

Posted on September 29th, 2009 at 8:07 am
redhead

I like some of the looks. Seems to be a smart and classy way to look current and fresh without falling for the younger trends. I also love boots! One question for Angie: When you pose for example pictures–are all the clothes and accessories yours or are you borrowing from a favorite store?

Posted on September 29th, 2009 at 8:11 am

YEAY!!! Thank you Angie for a wonderful post. I love when you post your outfits. You look amazing, as usual. The grey boots are beautiful. I would never think of wearing the other two pairs of boots to work because I deem them too casual, but when you pair them like that with beautiful dresses and accessories, it makes me think twice. So now I need to go back to my closet and rethink my boot strategy, which unlike my shoe strategy, is full of confusion. :-) I’ll report back on the forum.

Posted on September 29th, 2009 at 8:16 am

I agree with Tanya- my favorite posts are when Angie models a look for us. So cute! Every dress is gorgeous, every look fab. I’m glad you showed this because in all the discussions I just couldn’t see it working well. Now I get it!

Posted on September 29th, 2009 at 8:17 am

I love my new slouchy boots! I have “chicken ankles,” so it helps add a little balance on the lower half of my body. :) They are easy and comfortable.

Posted on September 29th, 2009 at 8:20 am
missrobin

Sorry, but the look evokes winter childhood memories of school girls who forgot their shoes and had to schluff around all day in their boots. IMHO, a fun look for some, but not elegant or classy–and at this point in my life, the slouchy boot look would be mutton dressed up as lamb.

Posted on September 29th, 2009 at 8:38 am

Gorgeous, Angie! Love the slouchy cowboy boots and apricot pearls. You look completely pulled together AND comfortable at the same time.

Posted on September 29th, 2009 at 8:40 am

As others have said, I love when you model your outfits! This is a look I’d need new frocks, boots, and lots of shopping guidance to pull off. The short frock length is scary but the stockings help. What especially appeals is that the boots can be loose around the calf and that it makes a dress more casual. I especially like your second outfit.

Posted on September 29th, 2009 at 8:50 am
Audrey

Angie, do you mind telling us about those fabulous gray boots? I have been looking for a pair in that color but have had a hard time tracking any down. Thanks!

Posted on September 29th, 2009 at 8:51 am
Antje

So fabulous! The look is very you; I love all the boots and adore especially the dress on the very left – soooo fab. I’d definitely wear the look, although I think I’m lacking the dress for it! My dresses are knee length and I’m not buying new things at the moment. But I’ll try this with my black shift dress.

Posted on September 29th, 2009 at 8:53 am

You’re beautiful Angie! I love seeing your outfit posts. That first look is to die for!

Posted on September 29th, 2009 at 8:54 am

I love your black slouchy moto boots. Paired with such a ladylike dress, it makes for a unique and very chic look.
Not sure how dresses fit into my new work wardrobe (well, they don’t) so that leaves two days a week and I would be more likely to do a slouchy boot with straight leg denim. I like the overall look though!

Posted on September 29th, 2009 at 8:58 am

You look adorable in this combo. You have a sharp eye. I love the apricot pearls with the chestnut colored boots. Actually, I love all 3 of your outfits equally.

I do have the same frock as you in the second picture, and the same boots as you have in the last picture. I could play with this look, with tights, for me.

I don’t want to shorten my dress to above the knee. Do you have dresses that you have shortened just for this purpose?

Posted on September 29th, 2009 at 9:01 am

No permission needed Rose and Joan. I’m flattered. Sinead, glad the penny dropped with this look!

Michelle, “short” is relative. With the exception of the frock on the far left, all I’m doing is lifting my hemline to show the knee cap. Trust me when I tell you that I am not one to wear short hemlines at all. I like skirts and dresses over my knee best, but that length doesn’t work with slouch boots, or any mid-calf boot for that matter.

Super you’re trying the look too,Tanya. It’s a fun way to dress especially when you’re sick of jeans like I am.

Sarah, I’ll write a post on how to wear mid-calf boots. It’s tricky but not impossible. There are a few variables you need to get right. Also, you don’t need to wear your skirt THAT short. Perhaps that was one of the missing variables.

Alecia, the grey boots clearly slouch at the ankles, just in a more subtle way than the other two styles. You can’t see the back of those grey boots but they slouch there too. Also, the frocks you wore with leggings are automatically shorter so remember that you have those to pair with slouch boots. It’s a great new look for your climate.

Hah! Redhead, everything that you see me wear and sport in the blog posts is mine (clothing, accessories and footwear). What made you think differently? I do have a huge collection of handbags that grows each year. I shall need a shrine for them soon. We all have our weaknesses.

Danja! I’m excited that I inspired your boot strategy. Like you, I err on the dressy side of dressy and how I like to wear slouch boots is with a smarter look. Also, my slouch boots are quite casual and flat, or low heeled. But you can go for dressier versions with higher heels. The devil is always in the detail!

Laura, it’s a style prerequisite to be practical and comfortable which is why two pairs of my slouch boots are flat! It’s the only way I can charge around town with clients.

Joy I can totally see you pull off the middle look because you’re a straight sheath gal like me.

Sandy, I haven’t had anything shortened for this look. Most frocks are shorter these days. It’s actually been hard getting frocks ay my usual knee length.

Good point Boof, and I’m blushing LOP and Antje.

Posted on September 29th, 2009 at 9:13 am

I’m looking forward to the “how to” post, Angie. Thanks!

Posted on September 29th, 2009 at 9:15 am

I am looking forward to the mid-calf boot how-to post too.

But what you hear right now is the sound of the penny dropping. :) I was immediately drawn to the first look on the left; I am in fact wearing a variation of it right now. The tall slouch boot and dress = the dressier look I need/prefer for work (although my hem is a bit shorter but still above the knee).

I adore the look of the mid-calf, but the slouch on that just reads as ‘too casual’ for work to my eye. Maybe if I paired it with a dressier, more structured dress (like the Classiques Entier neck-bow sheath) instead of one of my ‘canvas’ sheath… oooooohhhhhh. NOW I get it! LOL!

Posted on September 29th, 2009 at 9:26 am

I’m *very* drawn to the look, but am so scared to wear it at the same time. I just bought some slouch boots so I may experiment but am not sure I can pull off this look! But if you say that lasses of all sizes can wear this, I’ll try it. ;)

Posted on September 29th, 2009 at 10:02 am

Love this look, Angie, and you modeled it to perfection. I would be all over it this fall if I weren’t a) nearly 8 months pregnant and b) not an owner of slouchy boots.

Both of those will change in not too long! I just ordered the Frye look-alike boots that ChewySpaghetti found at Target (they restocked!!!) and am looking forward to trying them with jeans before baby and dresses and tights after (by December in Ottawa it’s far too cold to go bare-legged). I know they are not slouchy per se, but I love the look of them with dresses.

And then I plan to scour the post-Christmas sales for slouchy boots, hopefully in grey, which would be so useful in my wardrobe. I have a couple of dresses that would be perfect for this and I’m hoping that I will be able to fit them by early spring, in time for this look again!

Thank you for the photos. I always find the way you combine and wear your clothes to be aesthetically inspiring and enjoyable to to see!

Posted on September 29th, 2009 at 10:08 am

Wearing this look today!! I love it so far. Thanks so much for the how to for this! Sorry to be a broken record, but these posts are also my favorite as well. I love seeing how you make the looks work with items in your wardrobe!

Posted on September 29th, 2009 at 10:14 am
PalmFronds

Angie you look fantastic in those outfits, what an inspiration :-)

I have been dying to try out the slouch boots and have actually been looking for a wine-colored pair for almost a year now.When I tried them on in stores I always looked somewhat dumpy, but after reading your post I think the problem was atleast partially the length of dress I was wearing at the time so I’ll give it another whirl.

Posted on September 29th, 2009 at 10:23 am
klauren

Love this look – and now that I’ve seen it on you, going to try it! I want, need and desire those grey boots – been looking all over for just those – who/where?? Do tell Angie, please! And I agree with all the posters, when we see it on your lovely self, we get such an “ah-ha” moment, a picture sometimes worth a thousand words.

Posted on September 29th, 2009 at 10:37 am

Angie, your post yesterday inspired me to try boots without hose again and it just so happened I wore slouch boots with a short dress. I was worried the outfit would appear a little schizo. I was wearing a little cotton sundress with a wrap shirt, a leather jacket and slouch boots with no hose. As I knew would be her reaction, my grandmother was shocked I would wear a short dress with boots in fall weather. While it was a cool 60 degrees and windy in Minneapolis, it was nowhere near frigid! This post let’s me know I was indeed on the right track.

Angie, you always have your pulse on what I’m thinking. As always, I love the looks you’ve created above. Thanks!

Posted on September 29th, 2009 at 10:45 am
Debbie

Love the last look. I just don’t know if I can pull it off.

You by the way are beautiful.

Posted on September 29th, 2009 at 10:51 am

I won’t be wearing this look because I do not have the necessary components (and no money to obtain them), but that doesn’t mean I don’t like it.

Posted on September 29th, 2009 at 11:12 am

For sure! My favorite pair are my Diesel boots from last season, and they’ve got a chunky heel. I love pairing them with flirty frocks.

Posted on September 29th, 2009 at 11:13 am

YES! Slouch boots are definitely one of my very favorite trends this season! LOVE!

Posted on September 29th, 2009 at 11:13 am

It’s so great to see Angie modelling the looks it makes them seem more real. I love the look. think i need to post piccies cause i’ve got a couple of pairs of boots which i had got in my head to discard becuse they are too big round the calf but it looks as though they might work as slouch boots x

Posted on September 29th, 2009 at 11:18 am

I love the look of slouchy boots. I cant’ wait to find a pair. I particularly like how you paired them with structured, more conservative dresses.

Posted on September 29th, 2009 at 11:46 am

Angie–YOU LOOK FAB!!! (sorry for shouting)

Love it when you model looks for us. All three looks are so beautiful, and so you. I shall attempt to do a mom-on-the-go version soon.
However, won’t you agree that this is a look that suits those with slim legs?

Posted on September 29th, 2009 at 12:26 pm

Thank you for the visuals, Angie! All three dresses are so beautiful, and you have a great boot collection. I love this look, and though I own very few dresses, I am and will be sporting it this fall. It’s very comfortable and fun.
Oh yes, and these posts are my favorite, too! :)

Posted on September 29th, 2009 at 12:28 pm
Johanna

I think all three looks are winners, and the first one, though is more “traditional” so it’s not so surprisingly new. I guess I’m used to dresses with higher boots so far.

I am very short, 5′ 1/2′, so I know that I can get away with the first one, but the second and third? I am not so sure.

Posted on September 29th, 2009 at 12:35 pm
Johanna

I mean: 5′ 1/2″ hehe.

Posted on September 29th, 2009 at 12:38 pm

I love this look. Your photos are great! I have a few slouchy boots, but I haven’t paired them dresses yet, mainly b/c my selection of dresses is limited and I haven’t found a combo that I like yet. But I’m still trying.

Posted on September 29th, 2009 at 12:43 pm

I wish I can rock this look in my little tropical country. Unfortunately, I’d get weird looks.

-meream

Posted on September 29th, 2009 at 1:17 pm
Inge

I can’t write, I’m overcome by the fabulousness of that first dress!!!!-)

(but the answer is yes: I’m definitely into this look and as soon as I get myself a pair of slouch boots, I’m going to experiment with some outfits)

Posted on September 29th, 2009 at 1:35 pm
Mac

looks brilliant on you, Angie, but not sure I’d love it for myself. Will happily try on the look in the stores but not sure if I’m up for trying to master such a different silhouette…

Posted on September 29th, 2009 at 2:08 pm
Joelle

I have always thought slouch boots as a little messy looking so I do not own a pair, but you have shown that with tailored dresses the overall look can be very pulled together! I do have a few dresses that are just above the knee, so yes, I would try this look, if I find a pair of slouch boots that appeal to me.

Posted on September 29th, 2009 at 2:24 pm
Tiffany

I love all the dresses, but I’m afraid the look doesn’t really appeal to me.

Posted on September 29th, 2009 at 3:35 pm

That’s a great look, Angie. I can’t wait to give it a shot. But I think all my dresses are either too long or too short!

Posted on September 29th, 2009 at 4:02 pm

Indeed, Angie, you are a perfect role model. I am tempted to give it a try. I have the boots, but, like Antje, not quite sure I have the dress. I always try to keep an open mind.

Posted on September 29th, 2009 at 5:30 pm

I love the look! It’s my favorite, in fact I have some super soft Coclico boots I got a couple years ago that I like both slouched down and tall. They’re black, and I’m so fond of them that I’m thinking of getting these gray Coclico ones, too (not exactly the same style but with similar slouch-ability): http://www.pedshoes.com/coclic.....lorID=1548

Posted on September 29th, 2009 at 11:24 pm

Angie looks great but I can’t see myself doing this. My boots need to last for years, so I won’t be buying trendy and I have a strong suspicion this is not a good look for my short legged body.

Posted on September 30th, 2009 at 12:53 am
Iris

Those grey boots are gorgeous – such a nice, subtle muted palette. Where did you find them?

Posted on September 30th, 2009 at 1:54 am
Patience

This formula is wonderful. And Angie rocks it! I’ll be doing the best that I can with what I’ve got and I’m going to try it with skirts too.

Posted on September 30th, 2009 at 7:16 am

For those of you who liked the looks I modeled, thank you for the compliments.

Anne, you could sport the formula with a shorter leg line if you get the proportions and the dress and boots right.

I’m afraid you won’t be able to duplicate my grey boots! I bought them in an Italian shoe boutique in Hong Kong last year. They were my splurge of the season but worth every penny because they are so, so, so comfortable. The cost per wear has already whittled down to nothing :-)

Posted on September 30th, 2009 at 7:36 am

If my budget allows, I would love a pair of grey suede slouch boots. And if I had them I would wear them like crazy. We’ll just have to see. Charlotte Russe had a pair for $30, but now they only have them in brown, and I already have brown boots.

Posted on September 30th, 2009 at 11:01 am
fathenry

Ilove this look and will give it a try.that grey drop waist dress is so beautiful!

Posted on October 1st, 2009 at 6:43 pm

Angie, you have the most amazing dress (frock to you) and handbag collection. I’m marveling at that gray drop-waisted dress.
I love the tall gray boots, too.

Always such a treat to see you model a variety of concepts for us. I’m joining the chorus of readers who LOVE these posts, so please know that the effort on your & Greg’s part is greatly appreciated.

Posted on October 1st, 2009 at 7:02 pm

[...] the knee cap: As with mid-calf boots, shortening the hemline just a tad is important. Remember that you can cover up with hosiery if you prefer more leg [...]

Posted on December 17th, 2009 at 8:37 pm

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