Do you struggle to find the right tops and shoes to wear with your skirts? It can be really tricky! In general, skirts can just be difficult to style. Getting the top, shoes, and accessories just right takes some strategic thinking. Today I’m going to breakdown all the dos and don’ts to help you nail your skirt outfits every.single.time. You’ll see how to breathe life into the skirts you might already have hanging in your closet by pairing them with some classic, very intentional wardrobe basics.
If you’re looking for ways to take your timeless, classic outfits to a new level, with trendy updates, I shared my tips here.
How To Style A Skirt
Truth be told, I really don’t wear skirts all that often. As a work from home mom, you’ll most often find me in cozy loungewear, jeans, or more casual clothes. But…I know many of you do wear skirts. Maybe you work in an office, or you have a holiday party coming up and you want to bust out a pretty skirt. I know from working one-on-one with woman over the years as a stylist, that skirts in particular are among the toughest wardrobe pieces to style in a way that looks modern, on-trend AND flattering. These tips will take all the guesswork out of styling your skirts. Let’s jump right in…
Tip #1 – DO Choose Tops Carefully
My first tip is DO choose your tops carefully. When you want to tuck your top into your skirt, it can be very challenging…much like it would be with tucking in a shirt to a pair of pleated trousers. You don’t want to add bulk or extra fabric around the middle that accentuates a tummy. I think we can all agree that’s not a great look! Here are a few tops you can always rely on, that DO work with your skirts.
Silky Top
The most fail-safe top to wear with your skirts is going to be a silky top or blouse. The fabric is so paper thin and lightweight so when you tuck it in, there’s absolutely no bulk. Now, pleats will naturally add a little volume to your lower half. So, the last thing you want is to add even more volume to that lower tummy area by wearing a bulky shirt tucked into your skirt.
Above I’m wearing a pleated skirt with 2 silk tops. On the left, I’m wearing a sleeveless, washable (yay!) stretch silk blouse by Quince. It comes in 3 colors and is great quality…especially when you consider the $50 price tag. On the right, I’m wearing a long-sleeved blouse, also by Quince, also washable silk, and it comes in 18 colors! Both are so easy to tuck into the beautiful pleated chiffon skirt.
Note on sizing with Quince. If you want more of a tailored fit or if you’re between sizes, you’ll want to size down. But, if you’re looking for a slightly looser fit, go with your regular size. I’m wearing an XS across the board in all the Quince pieces featured in this post
White Cotton Poplin Top
Another really great option is to pair your skirts with a lightweight cotton poplin top. Again, the material is super lighweight so it’s easy to tuck into your skirts without adding volume. On the left I’m wearing a classic, white cropped button-down by Alice & Olivia with the same pleated chiffon skirt from the previous look. You’ll feel like you’re channeling your inner Carolina Herrera with this beautiful, sophisticated combination! Any cropped button-down will have less fabric to tuck in, making it a great option. On the right, I have on a super feminine high neck, ruffle, sleeveless top that’s a little more modern and feminine. You can’t go wrong with either!
Denim Top
Here’s an example of a top that might be a little tricker to tuck in. But, we can still make it a “do” versus a “don’t”! This is actually one of my favorite button-downs from Frank & Eileen. It’s made from a thicker denim material. I love how you can pop the collar and it stays up since the material is heavier! In this case, what you can do is wear a wide belt and tuck the volume of the shirt into the belt. OR you can even fold your shirt hem under and into your bra or bralette. This is a great hack to use when you are working with a top that has a bit of heaviness to it.
Sleeveless Cashmere Sweater
Sweaters can look great with your skirts…when you get it right. When in doubt, go with a lightweight sweater (cotton or cashmere are great!) that is shorter or cropped. This sleeveless mock neck cashmere sweater from Quince covers all those bases. But the distinction I really want to make about this sleeveless sweater is not only is it made from a super high-quality grade A cashmere, it also has an intentional finished bottom. So, you can wear the sweater out and over your skirt if you don’t want to tuck it in. This is a great option if you’re concerned about a lower tummy or have that menopause middle going on. Having that finished bottom also makes it easy to tuck it under and…it will stay put!
Can we take a minute for the accessories too? The leather handbag looks high-end designer, right? It’s actually super affordable at under $120. And the necklace I’m wearing with all of these looks is an amazing statement piece. I’ll link them both below…
Slimming Vest
This next look is little trendier. You might not have thought of wearing your vest with a skirt but because vests are fitted and tailored, they pair beautifully with skirts. A vest can look very chic and will highlight the waist perfectly. In this look, I swapped the black slingbacks for a pair of Veronica Beard pointed toe booties…I’ll get into the best shoes to pair with your skirts a bit more below!
Tip # 2 – DO Consider Proportion
This is a super easy concept, but it carries a huge impact when it comes to looking the most flattering in your outfits. Essentially, if you’re wearing something with more fabric or volume on top then go with a more streamlined bottom. If you’re wearing a baggier bottom, go with a streamlined top. Are there ways to look amazing with an all form-fitting or all baggy outfit? Of course there are (stay tuned for an example!) But contrasting volume proportion is a quick and easy tip to keep in your back pocket when you want an easy, reliable outfit combination. And it works great with skirts. Let me show you…
Silky Skirt & Sweater
In this look I’m wearing a slim fitting silk midi skirt with a looser fitting cashmere sweater. The skirt is SO comfortable and flattering. It comes in 17 colors (I own it in 2!) and it’s washable. Since it is more body-skimming, I paired it with the relaxed fit sweater which I did not tuck in. It has a finished bottom just like the sleeveless cashmere sweater I highlighted in Tip #1, so it looks very streamlined and chic…and it’s more tummy-forgiving!
Silky Skirt & Silk Top
Here I’m wearing the same midi skirt from the previous look, but this time a super thin and lightweight silk, tie neck top. This top is GOR….geous! It comes in 7 beautiful colors but the burgundy is so on-trend and perfect for the holidays. If you want to tuck a top into a silk skirt, you’ll want something like this. Since both the skirt and blouse fabrics are thin, you won’t get any lumps and bumps.
OK, speaking of lumps…a silk skirt like this one can sometimes show every imperfection so I’ll just throw on a shapewear skirt underneath to keep everything nice and smooth. You can even tuck your silky top INTO your shapewear to really guarantee no extra bulk around the middle! If this is a concern for you, wearing a darker color silk skirt will always be more forgiving.
Silky Skirt & Bodysuit
Ok so while I said it might be easiest to go with contrasting volumes on top and bottom, wearing more body-skimming pieces together can also work. Basically, wearing fitted with fitted isn’t a DON’T….it’s just not as easy to pull off. I wanted to share two looks to provide some inspo. First up, this open back bodysuit by Thistle and Spire. A bodysuit is going to be another top you can easily wear with your skirts whether your skirt is more voluminous on bottom or body-skimming. And this one really cranks up the sexy! You won’t have to worry about any bulky fabric to tuck in whatsoever. The sheer details and lace are truly beautiful…perfect for date night!
Silky Sirt & Mesh Top
Here’s one more top and midi skirt combo that falls into this fitted category. This Cinq a Sept top will work beautifully with skirts that are fuller and have more volume or skirts that are more streamlined like the silk midi skirt I paired it with. It’s super sheer and paper thin, but you still get great coverage. It has flattering ruching at the tummy and a cool, Parisian-inspired print. LOVE the bell sleeves too.
Tip #3 – Flattering 3rd Layer
Cropped Third Layer
When it comes to adding a third layer over your skirt, DO go for a cropped blazer, jacket or cardigan. The cropped hemline will give you that defined waist you want and a much more figure flattering shape. This blazer by Gray Lab is super affordable and gives this look a really cool vibe. The fit is wonderful, and I love the on-trend strong shoulders too.
Oversized Third Layer
Now for a third layer “don’t” when it comes to styling your skirts. I don’t recommend adding a bulky third layer. A long duster with your skirt is really going to just add volume all over. You might be warm and snuggly, but the proportions aren’t the most flattering!
Tip #4 – DO Add a Belt
9 times out of 10 your skirt isn’t going to have traditional belt loops like a pair of trousers would. This leaves you kind of in belt limbo…do you go with a thick belt, wide belt, medium belt, skinny belt? It opens up a whole can or worms. So, let’s simplify things. With many of the looks in this post, I’m wearing a thick, elasticized belt by Dior. First off, there is no excess to try to tuck into the front or back so a belt like this creates a clean, streamlined look. And, since it’s wider, you don’t need to worry about the skirt waistband coming below the belt. A 2’-3” wide belt that easily covers the waistband of the skirt will be a great option. It adds a modern interest that really elevates the overall look.
Bonus – you can also tuck some of the fabric of your top or sweater into a thicker belt to really minimize bulk AND create a more defined waist. So, the don’t here? Avoid a really skinny belt if you don’t have belt loops because it probably won’t stay put and you’ll be fussing with it all day.
Tip #5 – Make Strategic Shoe Choices
Pointed To Pumps & Skirts
If you’re getting frustrated trying to style your skirt, I’m going to bet that it’s because of 1 of 2 things. It’s either the top is too bulky and doesn’t work with the skirt OR the shoes aren’t quite right. Your first fail-safe shoe option is…pumps. Every.single.time. Just wear a pair of pointed toe pumps and you’ll create a long, lean, and flattering line. You don’t have to wear sky-high heels, kitten heels are super on-trend right now and they look lovely with skirts.
Dressy Booties & Skirts
Throughout this post, I’ve shown you a few different boot styles to wear with your skirts. While not as much of a slam dunk as the pumps, dressy booties can look really elegant with your skirts. When in doubt, a stiletto heel or on-trend kitten heel bootie is going to look better than a block heel. It’s just more feminine and refined. The other tip is to wear a bootie with your skirt that is fitted to the leg. This could be a sock bootie or side-zip bootie that hugs the calf. So, you can wear a shorter ankle bootie, a mid-calf bootie or a tall boot. All will work beautifully with skirts. Your fail-safe bootie option is going to be an ankle bootie or knee-high boot that meets the hemline of the skirt.
Tip #6 – DO Wear Tights
Our final tip for how to style a skirt is DO wear tights in a similar color as your skirt. This will be leg-lengthening and chic. Tights are also warm, which let’s face it, we are getting to that time of year when tights are a must in many climates. Does anyone else have horrible circulation and feel like their hands and feet are ALWAYS cold? I will just wear a pair of socks over my tights and under my booties for some added warmth.
I prefer a subtle pattern with my black tights like houndstooth, dots, or stripes. And I personally think it looks more elegant and refined to wear a sheer tight. It also helps create more of a contrast between the skirt and the shoe. Just remember that if you’re wearing tights with your skirt, you’ll want some type of slip in between otherwise you’ll build up static. The don’t here would be not to wear the old school, skin-colored panty hose. It can be done, but it’s tough to pull off! So, I’d tread carefully there and when it doubt, I’d go for black tights.
How To Choose The Right Skirt
Lastly, I wanted to leave you with a few tips for finding the right skirt for your body type.
- Triangle and Inverted Triangle Body Types – If you have a triangle or pear-shaped body type an A-line skirt will slim your hips, butt and thighs. If you have an inverted triangle body shape an A-line skirt can help create volume on your lower half to balance out the width at your shoulders.
2. Hourglass Body Type – If you have an hourglass shape, I’d recommend a pencil skirt or a fitted skirt to really accentuate your curves.
3. Apple Shape – if you have an apple shape, that’s where you really want to focus on making sure you have a sweater with a finished bottom that is untucked or maybe try a crop jacket over a longer sweater to give you that tummy forgiveness.
4. Length– For all body types, a safe bet when it comes to length is to go with a skirt that is in the knee zone. Either 2 inches above or below the knee is the most universally flattering hemline. Maxi and mini skirts can work too, but for that easy fail-safe skirt that works every time, then go with a knee zone hemline.
By the way, if you’re not sure what body type you have, this post is an excellent resource and the perfect place to get started!
Still have questions about how to style skirts? Leave a comment below. We’re always happy to help!
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