OUTFITS BY OCCASION Archives - The Well Dressed Life

Holidays at Home: Dresses and Jumpsuits

December 16, 2020 by Megan Kristel

One category I barely touched on this year is special occasion pieces. It’s crazy to think that we’ve gone almost 12 months without a wedding, a girls’ trip someplace fun, a Broadway show, or a fancy dinner out.

Not that I ever needed a closet full of cocktail dresses, but now, my kids ask me why I’m “dressed up” when I put on a pair of jeans.

The last time I got even close to dolled up was my 40th Birthday party last November. Just thinking about it makes me realize how much we all need a fun night out to blow off some steam.

Hopefully, that night is coming sooner rather than later.

For now, consider wearing something glam for the holidays, whether it’s Christmas cocktails with a small group or New Year’s Eve on the couch with Netflix.

Before you buy anything new, go in your closet, all the way in the back, and pull out something you saved for a special occasion. Throw that on instead of your leggings, pour yourself a glass of champagne, and toast to the fact that we survived this miserable year.

If you need some inspiration or want to pick up something new, scroll down to see some easy ideas in all sizes that will arrive just in time to celebrate.

Holidays at Home: Dresses and Jumpsuits

Velour Dress

Velour Dress, $25

Eat and drink all you want in this loose $25 velour dress. Just slip it over your head for an instantly elevated look as comfortable as wearing your favorite nightgown. To make it EXTRA extra, where you best jewelry and a bold red lip.

Long Wrap Dress

Wrap Front Maxi Dress, $99

I got really into long wrap dresses over the summer. They were a fantastic alternative shorts but felt infinitely more polished. See what you already have and consider wearing it around the house next week. Maybe add a gold flat or slipper. You’ll instantly feel the power of getting dressed and how it sets the mood for you and everyone in your home.

This one from Nordstrom is available in red and black, and can be worn year round.

Sweater Dress

Sweater Dress, $149

You likely have at least one sweater dress in your wardrobe, and maybe it’s not getting the wear you thought it would when you bought it. Go put it on! It’s the definition of one-step dressing. If you want to get dressed this holiday season without overcomplicating things, the sweater dress is your best bet.

If you need one, I love this option from Ann Taylor, with the one-shoulder buttons. You can wear it now, at home, and then take it to the office with tights and boots. Available in sizes XXS – XXL.

Jumpsuit

Metallic Jumpsuit, $149 (ON SALE $75)

I adore this metallic jumpsuit from Banana Republic available in all sizes including petite and tall. It’s super flattering on, defining your waist and pulling the eye in with the faux wrap style top. Do me a favor and never ever wear it with the ankle boots shown above. Opt instead for a strappy heel if you need some extra height or a simple pair of flats.

Sequin Dress

Sequin Mini Dress, $54

When I was in my early 20s, my friends and I threw a New Years Eve party (these days I’m lucky if I’m awake when the ball drops). For fun, my girlfriends and I bought ridiculous, cheap cocktail dresses. They were gaudy, but also kind of fabulous.

This season, Express is killing it with affordable holiday options that remind me of that night. Why not wear something you otherwise would never wear, like a sequin covered dress.

But, I’m thinking this sequin sweatsuit is the PERFECT outfit to wear to kick 2020 to the curb. Gaudy, but also kind of fabulous 😉

Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers.

Recommendations are based on my experience as a personal stylist and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail.

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

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Holidays at Home: Fun and Festive Pants

December 16, 2020December 15, 2020 by Megan Kristel

Yesterday, we featured five chic and affordable sweaters to wear while we celebrate the holidays at home. Today, we’re talking pants, not just any old pair of pants, but fun, festive, and slightly over-the-top.

After a year of sweatpants, leggings, and joggers, I’m ready for the opposite, like silk drawstring, velvet pull-on, and sequin-covered bottoms.

I know many readers plan on going all-out with their looks this holiday, despite the fact (or because of the fact) that this year was the worst and our gatherings might be smaller than usual.

I plan to do the same, but I want it to be easy.

A great tip is to pull your family’s outfits together now, so you can avoid the last minute trip to Target for tights, shoes, etc. And don’t forget about yourself! In years past, I stopped short of my own outfit, and, of course, I ended up scrambling at the last minute.

Holidays at Home: Fun and Festive Pants

Prices are subject to change, so please keep that in mind, and inventory across the board is limited and selling out quickly. As always, there are plus, petite and tall sizes available in several of these options. All of the featured retailers have holiday delivery.

Velvet Pants

Velvet, $118 (ON SALE $59)

A pair of velvet pull-on pants may be the definition of glamorous comfort. They make pulling together a holiday look so easy, and they feel like sweatpants. Pair with a tonal sweater for an elevated monochromatic look.

Available in Regular, Petite and Tall up to a size 24, in colors dark spruce (above), navy and black.

Satin Drawstring

Satin, $89.50 (ON SALE $45)

Personally, I think I am going to host Christmas Eve in these satin drawstring pants and a black sweater, then glam it up with accessories (Thursday’s post!). Like wearing pajamas but better.

Available in XXS – XXL on sale for under $50.

Plaid High Waisted Ankle Pants

Plaid, $25

While I would NEVER wear these in public, there is something so fun about them. If you’re hosting a small gathering why not wear something way out of your comfort zone.

These plaid bottoms from Old Navy are only $25, available in all sizes including regular, petite, and tall up to a size 20.

You can keep the look simple with a basic black sweater, or go all out and pick up the coordinating plaid sweater! Just ditch the ankle boots and, instead, wear a simple flat like the Birdie velvet loafers.

Sequin-Covered Trousers

Sequin, $54

Express has some fun dress up pieces right now. So many I had a hard time picking just one. But these sequin covered trousers are the perfect way to send 2020 packing. They have a relaxed fit and are ankle length, so you can wear them with a flat or a heel.

I would wear these with a grey slouchy sweatshirt to balance and black heels for New Years Eve in front of the TV or, pair them with this $25 fuzzy white sweater featured in yesterday’s post.

Available in Regular and Petite in XS – XL.

Faux Leather Leggings

Leather, $98

Finally, these Spanx Faux Leather Leggings are a long time reader favorite. If you already have them, wear them with a basic or sequin-covered tunic, depending on your tolerance for bling. Find more styling options in our post How to Wear Faux Leather Leggings.

Available in XS – XL here and plus size here. Buy one size up.

Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers.

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

How to Dress Up Leggings for the Holidays

December 7, 2020 by Megan Kristel

Today we’re talking about how to dress up leggings for the holidays, so you can maintain your 2020 comfort level while looking festive and chic. Because, if ever there was a year to embrace loungewear as holiday attire, I guess this is it.

First, let’s talk about the kind of legging. Contrary to popular belief, not all leggings are created equal. For these looks, you do not want to wear the leggings you wear to work out.

Just like we keep gym sneakers separate from “dress up” sneakers, leggings follow the same rule. Gym leggings will look out of place.

My hands down, absolute favorite pair of all time are the Zella Live-In leggings. Even though they are sold as work out bottoms, I prefer to use these as my “better” pair.

These higher-waisted leggings are thick, and pull you in and lift you up while still being comfortable. I have had several pairs for years and I am always amazed at how well the wash. They don’t fade or stretch out over time.

Zella Live-In Leggings

Leggings, $58

Style note: If you’re not totally comfortable wearing traditional leggings, swap these out for your Spanx Perfect Pants, you’ll feel more finished in them. Want to make these looks extra special? Wear the Spanx Faux Leather Leggings OR their new Velvet Leggings.

For the outfits below I worked with a combination of items I know you have and added in some new affordable pieces to help build out your options.

How to Dress Up Leggings for the Holidays

Cozy Glam

Sweater, $40 |Loafers, $95 | Hair Bow, $10 Studs, $40

This first look is simple yet chic. I like leggings because they allow you to wear a big oversized sweater, and this one from Express is fab. It’s on sale for $40 and comes in four colors up to an XL. Above, I’m using the grey because I love the neutral combination. There is also a seasonal red that would look lovely.

Then, I used the Birdie loafers we are all loving, in black velvet. For accessories, a fun pair of CZ studs and a simple velvet bow hair tie I found on Etsy.

Chic by The Fire

Sweater, $52 | Thermal Tee, $12 | Booties, $125 Beanie, $19

Many people are getting creative this year, hosting smaller get-togethers outside. Whether you’re sitting by a fire or snuggled up under a heat lamp, this look would be adorable. I created a simple column of color by adding the popular Old Navy long sleeve tee (another reader fave) as a base. Then, I found (and ordered for myself) this Fair Isle wrap cardigan.

When I first saw it, I swore it was expensive, but much to my delight, it’s another Old Navy find for under $50 available in regular, petite, and tall sizes.

Then I used these Sam Edelman tan booties. In our INSIDER group, we talked about when you can wear tan shoes with black bottoms and when to keep it to all black. My best tip is to add the tan to a look when it is casual because it will elevate it and add interest. If the outfit is more formal, keep it to black.

Finally, a hat is a fun accessory. You’ll stay warm and bonus points since you won’t have to do your hair.

Classic Combo

Tunic, $25 | Earrings, $12 | Mules, $88 | Lipstick, $28

This last look is as easy as it gets. Add a long white tunic, like this one from J.Crew in all sizes up to 3X for $25. You want this to feel and look oversized.

I love the look of an over-the-top earring with a collared shirt. It feels dramatic and perfect for the holidays. Here I used this $12 pair, also by J.Crew. These are big and will add some movement and glamour.

Speaking of glamour, holidays at home should be a little extra, so I went with these gold fur-lined slipper/loafers and, for an added touch of flair, a bold red lip with my go-to brand Kosas.

Tell us below, what are you planning on wearing at home this holiday?

Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers.

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

5 Fair Isle Sweaters for Thanksgiving and Beyond

November 20, 2020November 20, 2020 by Megan Kristel

I usually wait until after Thanksgiving to decorate for Christmas, but I started this week. My kids have been in full-time, in-person school since the start of the school year (it’s been wonderful) but are going virtual for two weeks, beginning on Monday.

Knowing the next few days will be filled with distractions, I’m putting in a marathon effort this weekend to get the holidays set up.

This year I want to make it as cozy and fun as possible. That shouldn’t be too hard since Vivi turns two a few days before Christmas. Getting to redo all of our holiday traditions with a little one again has been an absolute gift. I’m not sure who is enjoying it more, her or me.

One of my favorite childhood traditions was how my mom made sure we always had a few special things to wear, like pajamas just for Christmas Eve and a new Christmas Day outfit. Of course, I do the same for my kids. Because what we wear can set the tone for the occasion and end up marking a memory.

And for me, there is no pattern more memory-evoking than a Fair Isle print.

So as we head into the weekend, I’m rounding up some of my favorite cozy Fair Isle sweaters for holidays at home. They are perfect for this time of year, for Thanksgiving, the night you decorate your tree, or just snuggling on the sofa with a holiday movie.

5 Fair Isle Sweaters for Thanksgiving and Beyond

How fun are these? They’re the stuff of Hallmark Movie magic. If you pick one up, or already own one (and you really only need one) keep your look simple: a pair of jeans, a pull on pant, or a jogger, the pour yourself a glass of wine and relax by the fire.

Below are my top picks in all sizes including regular, tall, petite and plus:

LL Bean, $75

Vero Moda, $65

Gap, $80

Gap, $70

Ann Taylor, $90 (On Sale for $45)

Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers.

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

A Classic Grey Dress Two Ways

November 19, 2020 by Megan Kristel

We talk a lot about creating a chic and classic style on a budget. No matter your budget, you have one, and you need to know where to splurge, spend, and save. The best tip I can give you is to be selective about every item you bring into your wardrobe, especially those pieces considered a bargain.

Inexpensive, sale-priced, clearance items tend to be where we let down our guard. It’s too easy to throw a $20 top or dress in our carts. But what happens when we do that repeatedly is we end up with a closet that doesn’t make any sense.
You’ve been there, I’ve been there, we’ve all been there.

That’s why it’s important to know the style you are trying to achieve before you shop, and then hold even the most affordable item to that standard.

Today’s dress, this simple Ponte shift from Old Navy, is on sale for under $30. It is the perfect example of what to look for in a “save” piece that adds tons of value to your wardrobe.

Old Navy Ponte Shift Dress

Dress, $28 (Missy, Tall and Petite, up to XXL)

Ponte knit is ideal for this time of year. It’s stretchy, soft, and has a great fit. You can dress it up or down. It pairs with everything from tall boots (below) to sneakers and a denim jacket.

This dress works so well because of its timeless cut and heather grey color. It’s also not too short, so you can take it to work, dinner, or even a relaxed Thanksgiving.

Today, I’m showing you two sophisticated looks with this inexpensive piece at the center.

Layered Neutrals

Boots, $268 (Black Friday sale $134) | Coat, $173 | Scarf, $39 | Earrings, $90

To say I love this look is an understatement. My favorite way to dress is in layered neutrals. It creates such a gorgeous richness that works for any occasion.

Here, I paired the dress with these stunning cognac boots from Banana Republic, currently on a Black Friday sale for 50% off. Sizes are getting limited.

Then, a classic camel coat. I picked up a similar jacket last year and have got so much wear out of it. I like this one from Express; it has a flattering tie waist without looking like a bathrobe.

Finally, add an ivory scarf (under $40 at Nordstrom) and pretty pearl and gold statement hoops.

Simple, classic, timeless.

Basic Black

Booties, $105 | Tights, $15 | Belt, $45 (on sale $15)| Earrings, $7.50

When you focus on wardrobe building, you’ll eventually get the point that you already have everything else you need to create a fresh look when you bring in one piece.

This look is an example of that. You likely already have a pair of black ankle boots. If not, these booties by Vince Camuto are on sale at DSW. Their block heel makes them incredibly comfortable. Pair them with opaque tights to give your leg a long line.

Then, I added this gorgeous belt from LOFT. Right now, it’s on sale for only $15. It’s subtle but has a designer look and feel. Wrap it around your waist to bring in some visual interest.

Finally, small door-knocker earrings mimic the belt buckle’s style, creating a cohesive, thoughtful outfit.

Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers.

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

The Best Selling Over-the-Knee Boots I LOVE

November 12, 2020November 12, 2020 by Megan Kristel

Over-the-knee boots have been popular for some time. Over in our Facebook Private Group, I get questions about them frequently. Specifically how to wear them and if they are age-appropriate.

So let’s start with the question of age. It’s simple. AGE DOES NOT MATTER. The Well Dressed Life is all about helping you achieve a modern and classic style, which is inherently timeless and ageless. I break down my philosophy on age and “appropriate” dress here.

For style inspiration, you have a lot of options. But first, lets talk about the boot.

I wanted one that was versatile, affordable, casual and easy to incorporate into my uneventful life.

Last December, I started to hear (unsponsored) praise for these tan suede over the knee boots for under $50 from Amazon on social media, so I decided to give them a try.

I’ve had them for almost a year now and still highly recommend them.

The Best Selling Over-the-Knee Boots I LOVE

Boots: $45, Jeans: $80

I will never be comfortable posting pictures of myself, but thank you to everyone for being kind. I know the pictures are helpful, even though I feel like a major dork in them.

For some context I am (almost) 41 and am 5’10. However, I found these on Pop of Pippi’s Instagram and she is petite and looks fantastic in them. So don’t be afraid to give them a try if you are petite (and follow her Insta for some great petite looks).

Are they the best quality? They do the trick, which is to let you wear a trend while it’s popular without feeling committed to it and spending a small fortune.

They are surprisingly comfortable. The block heel gives nice support and they are not too high making them super easy to walk in.

I paired them with the Joe’s Curvy Skinny Ankle Jean. (On sale for $80 at Nordstrom Rack – they usually retail for $189). I LOVE these. They are high waisted, with nice stretch. But the slide over any skinny jean easily.

I’ve worn them a few different ways, usually with jeans (above) or leggings and a long cardigan (below). The key is to keep it simple. Almost think of them as pants, if that makes sense.

This weekend I’m going to wear them with this black sweater dress from the J.Crew factory sale for dinner on Saturday (I’ll share over on Instagram).

View this post on Instagram

☕️Working from home today and decided to break out my new over -the knee boots! . Did you pick them up last week? . When I need to have a productive day at home, getting dressed makes all the difference. . So I threw on my favorite leggings, a simple tank and this popular long cardigan I’ve featured a few times. . Already crushing my to-do list. 😉 👆🏼to see all my outfit details follow the link in my profile and click ”Shop My Outfits”

A post shared by The Well Dressed Life (@thewelldressedlife) on Feb 24, 2020 at 10:24am PST

I original purchased the tan suede, and just ordered them in black for the holidays. I think the suede adds a richness to the look but again, has a casual vibe.

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Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers.

Recommendations are based on my experience as a personal stylist View Post and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail.

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

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A $30 Blazer for Work

November 5, 2020 by Megan Kristel

These days, workwear leans a little more casual than usual, which can make getting dressed feel redundant and boring. Instead of feeling like you’re limited to the same old outfits, use it as an opportunity to try something new.

This classic patterned, oversized blazer is just the thing. It’s only $30, available in regular, tall, and petite up to a size XXL. Whether you’re working from home (and running to Target in between conference calls) or heading into the office a few days a week, scoop this up and get inspired.

Old Navy Oversized Blazer

Blazer, $30 available in regular, tall, and petite up to a size XXL, plus size option here

When incorporating a trend or a style outside your comfort zone, it’s important to maintain some timeless elements. This is what helps your look stay modern. Here, I’m using an oversized blazer (trend) with a houndstooth pattern (timeless). The combination strikes the right balance, and the price point allows you to give it a try without making a significant investment.

Below are two outfits, created with items you already have, and a few you can easily pick up to continue to expand your wardrobe.

Target and Conference Calls

Making a casual look fresh and pulled together comes down to combining casual pieces with a few polished ones. It’s that tension between a sneaker and a proper handbag that is unexpected and modern.

Here, I’m layering the blazer over a grey sweatshirt. Fit-wise, this works because the blazer is oversized. Use a sweatshirt that is lightweight and not too boxy. It’s extra cute if you have one with a zipper and hood. Use whatever you already have; just be sure it’s thin enough to fit under the blazer.

Then, a pair of sneakers. These Cole Haan sneakers continue to be a best seller. I love using them in outfit posts to show just how versatile they are. The British tan accent on the shoe tongue gives them a sophisticated feel and pulls out the blazer’s rich tones.

To keep the look cohesive and add the right amount of structure, I used a similar color bag. This one is from ASOS for under $25.

For bottoms, grab a pair of casual jeans. I’m using light-washed ankle length boyfriend jeans because I like the contrast. You can wear whatever you prefer, from dark wash straight jeans to distressed skinnies.

In the Office

When I create these outfit posts, I always want to provide some helpful tips. Maybe it’s an unexpected way to wear something or a product recommendation you end up buying and loving. Then, I want you to feel inspired. Perhaps you have similar items hanging in your closet and never thought to wear them together until now.

Finally, and perhaps what makes this site different from other style sites, I want you to build a functional wardrobe. You’ll see items repeated throughout a season and even the year because that’s how we dress in real life.

The blazer works with so many items many of you already have, like your favorite black jeans. Or go ahead and wear it with the Spanx Perfect Skinny Black Pants. It will look fantastic.

Want to kick the style factor up even more? Try wearing it with these leather leggings.

To give you some variety, above, I’m featuring them with these new to me, Curves 360 by NYDJ Ponte pants. If you want a slim cut pant but don’t like skinnies, give these a try. You’ll create a similar look in a more flattering cut. These are available in all sizes, including petite and plus.

Because these pants are straight leg, you can easily wear your favorite ankle boot. Just remember that the pants’ hem should sit on the top of your boot, creating a break.

If you have the Sam Edelman Walden booties, wear them, in either black or tan. Above is a different Sam Edelman in classic black leather, with a higher shaft. These work well with straight or bootleg pants.

I’m using this washable wool crewneck from the Banana Republic, another Reader Fave, in vanilla cream to layer under the blazer.

Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers.

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

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