The Holiday Lookbook: 6 Outfits from Casual to Dressy

Thanksgiving Ready.
Why is it a Find? These velvet joggers will rival the turkey for the star of Thanksgiving Day. While velvet is automatically thought of for dressier looks – and you’ll see that more below – with it’s popularity this season, it dresses up the most casual of silhouettes to make it the perfect solution for Thanksgiving. Eat in style, ladies.
Wear it with: We’re showing these joggers with an updated cableknit sweater that feels so right for Thanksgiving. The contrast fabric and nice drawstring cord at the waist are lovely touches, so you can absolutely tuck just a bit of your sweater into the front of the pants, to ensure your outfit doesn’t look too slouchy. (Feel free to untuck post-dessert and thirds.) And this styling trick can be done with a chambray or plaid button down shirt, too. Dress them up with heels and a silky tunic or sparkly top throughout the holiday season.
Fit Tip: From XXS-XL, and Petite too, the modern fit is a dream for anyone. They have a slightly cropped length that hits just above the ankle on most, and the elastic waistband isn’t too tight.
Alternatives: There are a couple of other pretty colors to choose from through the ‘shop it’ button. Alternatively, Eileen Fisher’s black version has a more generous, relaxed fit (in S-XL) and can easily dress up with a silk tunic and heels. J.Crew’s wool pants have the same ease of the featured pants, with an elastic waist, and a playful piping detail. If you’re a dress gal, this Anthropologie maxi dress has a gorgeous pattern of Thanksgiving color that is just as comfortable for a day of eating.

Why is it a Find? This fresh take on a classic cable-knit sweater perfectly balances the velvet joggers featured in this outfit. The looser cable stitch (that isn’t see-through) and blend of tencel in the wool fabric ensures you won’t get overheated while doing any final cooking prep. Made by Shae, a brand we loved when we had retail stores too, they really deliver with this one.
Wear it with: We love it with the velvet joggers in this look, but really, what doesn’t it go with? It looks great with jeans of any style, corduroys, cargo pants, and casual skirts. It’s also cute layered over a plaid shirt.
Fit Tip: In sizes XS-L, and Petites, the fit is modern and easy, meant for a relaxed fit throughout the body. And unlike so many easier-fitting sweaters, this one isn’t too long, hitting at the lower waist on most ladies.
Alternatives: J.Crew updates their version of a cable knit with a stylishly ruffled cuff and comes in some great colors. If it’s a truly soft and cuddly fabric you’re after, this chenille cowlneck works with the velvet joggers and doesn’t have the weight of chunky wools or cashmeres. If you prefer the versatility of a cardigan that can be worn over a lightweight tee or turtleneck, the striped color combination of this longer open cardi is so Thanksgiving-right.

Why is it a Find? The cropped length and rich feel of the velvet featured pants in this outfit look so great with the more tailored wool texture of these amazing Matt Bernson loafers. The cognac brown leather outsole and heel (with a pretty braided detail) pull all the neutral colors of this look together in style.
Wear it with: Besides the look we’ve put together here, these loafers are perfect for the office with trousers or with any of your jeans on Casual Friday and all weekend long. Wear them with little invisible ped socks or a patterned pair of socks for some fun (with longer pants).
Fit Tip: They run true to size.
Alternatives: If your size is sold out through the ‘shop it’ button, head to Shopbop, where you also get free shipping + returns (and can use your Amazon Prime account). Instead of the polished look of these wool loafers, you can choose to add a playful finish with these metallic Converse sneakers.

Why is it a Find? Simple, yet undeniably stylish with this outfit, the neutral tones and timeless natural horn perfectly offset the modern velvet jogger pants and updated cable knit of the sweater.
Wear it with: This outfit, and any earth-toned look, will make you reach for these earrings.
Fit Tip: Click through the ‘shop it’ button to see the alternate image where you can get a sense of the ¾” size.
Alternatives: You can also finish this look with a little sparkle in your earrings. The brown and clear stones speak to the neutrals of the outfit, while the blue stones adds just the right pop of color.

Any & Every Casual Holiday Gathering.
Why is it a Find? Whether you’re celebrating Christmastime, New Years Eve, or anything all winter long, this MICHAEL Michael Kors gold sweater is a perfect choice. With just the right amount of subtle shimmer, and an elegant draped back, it makes an otherwise simple lightweight sweater anything but basic. And at the amazing sale price, it is selling out everywhere, but we found some at Belk (with free shipping), so snatch it up before it’s too late.
Wear it with: We’re showing off this top with easy black trousers. But really, the sky’s the limit, so check out our alternative options in the pants to the right – lace skirts, coated jeans…there are just so many ways to style this top. It is lightweight, which we love since parties can get warm, and you can layer this beautiful nude lace cami underneath - hints of the the subtle lace pattern show through the sweater back opening and poke out of the hem to give it just the right sexy allure.
Fit Tip: Click through the ‘shop it’ button to see the simple crewneck styling of the front of this sweater. In sizes XS-XL, the modern fit and high hip length looks great on every lady.
Alternatives: Rebecca Minkoff’s contemporary red cashmere version is tied with the featured sweater for one of our favorite Finds of the holiday season. With a similar open back detail, the slightly flared hem of the body and sleeves make it universally flattering – especially with a slim skirt or pants. Alternatively, sparkly sequins, found on Neiman Marcus’ modern-fitting cashmere ½ sleeve top and Free People's navy short sleeve top, go a long way to holiday style…all the way through New Year’s.

Why is it a Find? Vince’s ankle length pants merge dress and casual ease with a pull-on, elastic waist and tailored trouser styling – ideal for the holidays, especially if you’re not sure how dressy everyone else will be.
Wear it with: The banded hem of the featured sweater in this outfit conceals the elastic at the back of the waistband, but you can also wear a tunic or a top that you can just tuck in a bit at the front. The versatile fabric works year round, and if you’re wondering how to handle the cropped length on a really cold day, you’ll see we’re showing booties that will come up under the bottom of these pants. But any shoes look great – heels dress these pants up, loafers and oxfords give them a tailored finish, and cute sneakers give them an even more casual edge.
Fit Tip: Vince’s modern fit and elastic waist ensures comfort – so go ahead…that eggnog is not going to drink itself.
Alternatives: For a sleek and sexier look, nothing beats 7 For All Mankind’s coated black skinny jeans – they have great stretch and a flattering mid-rise in a contemporary, not-too-skinny fit. A lace skirt in rich red or deep forest green will dress up this sweater and surely show off your festive flare.

Why is it a Find? Fur details add such a rich finish to any cold weather outfit, and over the holidays, it’s surely time to embrace this trend. Madewell’s vest lets you do it without breaking the bank on a real fur – and it’s a lot more PC.
Wear it with: The timeless black color and simple style adds fun flare to the gold shimmer sweater and simple black pants in this look. And it allows you to basically make 2 outfits out of the sweater – this covers up the dramatic back, and then you can take off the vest for a big reveal. Unlike some, this vest is not too fluffy, so you’re not adding bulk to your silhouette. It has hidden hook closures, but we love it open – over a simple tank, a plaid shirt, or any festive top.
Fit Tip: Madewell’s modern fit – similar to its parent company J.Crew – is meant to lightly skim the body and easily layer, in XS-L.
Alternatives: If your size is sold out through the ‘shop it’ button, Shopbop may still have it (and you’ll also get free shipping + returns – you can even use your Amazon Prime).

Why is it a Find? Since we are putting this outfit together for a holiday look, continue to play up texture, by finishing it with these velvet booties from MICHAEL Michael Kors.
Wear it with: Here, the rich black and gold accents pull this outfit together with ease. And we adore how they look with the tailored Vince trousers, adding holiday style to such timeless pants. But don’t be tricked - these are not just for special occasions. That is the beauty of velvet, especially this season. These booties look amazing with jeans and a cozy sweater or casual top, yet they can be paired with a great dress and black tights for an edgier, night-out look (even a cocktail party).
Fit Tip: They run true to size, and the block heel makes them easy to walk in, regardless of the weather. A little fabric protection spray will ensure they stay looking good for a long time to come.
Alternatives: Sam Edelman’s suede wedge booties also look great and give you enough ankle coverage for the cold weather.

Office Party Appropriate.
Why is it a Find? Really, we haven’t seen anything this chic, and yet still office appropriate, in a long time. David Meister has outdone himself with this sheath dress, and we are trying not to drool – too much. Conservative and insanely figure-flattering, this will quickly become your go-to for most any occasion. Sure, it works for the office holiday party, but you’ll feel appropriate all day (even if you have an important meeting) and you’ll reach for it when you have an important dinner, Bar Mitzvah, and any occasion you want to feel confidently elegant.
Wear it with: Black hose and your best heels are all you need to complete this look in style. Jewelry accents can effortlessly change up the feel of this dress, as we’re showing with this look below.
Fit Tip: David Meister is known for his wonderful fit. The brand is a red carpet favorite, and the modern fit isn’t too slim, available in sizes 2-14, it’s meant for every lady. The draped front works on every chest size and cleverly conceals any belly bumps, while the belted waist shows off the slimmest part of your torso.
Alternatives: If you prefer an outfit in some holiday color, Nanette Lepore’s wine peplum jacket and matching pencil skirt has an equally conservative appeal, in a contemporary (but not too trim) fit and modern edge that is office party right.

Why is it a Find? For the office, especially if you work in a conservative space, you’ll never wrong with a great pair of black leather pumps. And these Cole Haan ones have a pretty scalloped edge that give them just the right amount of style. Truth be told, it’s the padded insole and GRAND.OS flex molded sole that really won us over – these are seriously comfortable.
Wear it with: These will quickly become your go-to pumps thanks to Cole Haan’s high quality attention to detail and comfort construction.
Fit Tip: They run true to size.
Alternatives: This gorgeous dress will look just as good with suede heels in rich holiday color, like these comfortably cushioned, dark green suede Cole Haan pumps.

Why is it a Find? Gorgeously edgy with a touch of green that doesn’t scream “holiday”, these Alexis Bittar earrings are the perfect add-on to the timelessly classic dress and pumps in this look.
Wear it with: They are dressy enough to wear for a truly formal event, and we love them as a stylish finish to more casual night out looks, too. They look great with jeans and a cute date night top.
Fit Tip: Click through the ‘shop it’ button to see the alternate image on mannequin to get a better feel for the 1.2” size.

Why is it a Find? Playing off the touch of green and sparkle in the earrings we chose for this outfit, Ann Taylor’s chunky statement bracelet is a great finish. Another piece that’s easy to throw in your tote on the way to work and slip on before you head to the party, the bracelet-length sleeves of the featured dress will show off this well-priced bracelet when you are raising your glass for a holiday toast.
Wear it with: Sure, you’re going to add this to any outfit over the holidays, and the green/pink/clear color combination ensure you’ll get to wear it all year long. And don’t wait for just a special occasion – it adds a fun finish to jeans and a tee or simple sweater.
Fit Tip: It’s stretchy, so it slips on with ease.

Office Party Style.
Why is it a Find? A blazer is always right for the office, and this one from James Jeans adds an air of festive celebration in its velvet fabric that is finished with satin lapels. Perfect for the party, and totally appropriate all day long – on the day of the party, you’ll find most people are just a little more dressed up and ready for the fun that is coming.
Wear it with: You can dress it up with a lace top and fitted black pants, as we’re showing in this look, and thanks to it’s high hip length, it can even be worn with a skirt or sheath dress. It will add instant pizazz to jeans and a simple tee or blouse, too.
Fit Tip: The single button closure is ideal for every lady, regardless of your chest size, ensuring this jacket won’t buckle or gap when closed. In Petite – Large, the contemporary fit isn’t too trim with plenty of room in the body to even layer over a slim sweater. The higher hip length keeps it from overwhelming even the most petite ladies.
Alternatives: Velvet is THE fabric of the season (as you may be noticing from this guide), so there is a velvet blazer in every fit – J.Crew’s 2-button has a lean and longer shape in their modern fit, Madewell’s collarless longer version is ideal if you prefer a bit of a more relaxed look & fit, and Anthropologie even has a version with a beautiful silver/black floral pattern. And they’ll all work with the rest of the outfit we’ve put together here. J.Crew also has a gorgeously classic wool tuxedo blazer with satin lapels  for a truly timeless option.

Why is it a Find? Holiday dressing isn’t just about adding red and green color accents. This gorgeous cobalt blue and black lace top from Cooper & Ella is a wonderful alternative that is just as festive, and such a flattering color for most every skin tone. The crew neckline ensure you can wear this top comfortably with the office crowd. And in a creative environment, you can absolutely wear it all day long.
Wear it with: We love how this shape is easy to pull-off with slim trousers, skimming over the waist and high hip area. And since it’s not too long, this top can also dress up a pencil skirt, wide leg trousers, or your favorite dark wash jeans.
Fit Tip: The armhole is slightly cut in to elongate your arms and add definition to your shoulders, while still concealing your bra straps and ensuring office-appropriate coverage, even if you remove the jacket featured to the left. The length hits just at the high hip on most ladies, so no need to tuck in for a polished appearance, and the body-skimming shape isn’t too fitted in your normal size – XS-L.
Alternatives: The blue lace of this top is so stunning, we also love it in this cold shoulder style. This blazer outfit we’ve put together here can also take on a bit more casual feel with a plaid shirt (also available in a blue/black combination), or create a more tailored appearance with Free People’s wine-colored feminine tuxedo blouse or J.Crew’s ruffle version. If you are opting for one of the longer or relaxed velvet blazer options we suggested to the left, this Nic+Zoe relaxed blouse will look lovely underneath.

Why is it a Find? Theory is a brand that is always office-right, and these Italian knit ponte pants are no exception. The fabric has a wonderful weight to it that, along with equally fabulous stretch, keeps things smooth and creates a lovely clean line. The stretch means you can indulge in some of those holiday treats in comfort – and they’ll hold their shape really well (no baggy knees).
Wear it with: The knit fabric really lends itself to any look. We’re dressing them up here, but you can wear them with a tunic style sweater for a casual look, or with any tailored top for a day at the office. Any shoes will work from sneaker and loafers to heels to booties, think of these pants as the perfect blank slate.
Fit Tip: Theory’s contemporary fit runs true to size, in sizes 0-12 for a slim, fitted appearance. They are cut to hit just above the ankle, but if you are petite, they look just as good full length.
Alternatives: These pants also come in a gorgeous shade of deep cherry red through the ‘shop it’ button. And J.Crew’s wool version has wonderful stretch too, available in their typically modern fit and a slim silhouette from Petites to Talls. Alternatively, Everlane’s flannel wide leg pants are amazingly priced for such a luxurious and soft wool/cashmere fabric that is available in rich neutral shades.

Why is it a Find? These heeled suede loafers from Franco Sarto have a tailored appearance for the office, while the kiltie detail and comfortable block heel add some special interest that holds up to the rest of this outfit, so you won’t need to change your shoes for the office party.
Wear it with: The ankle length of the Theory pants in this outfit show off these shoes, but long pants – even wide legs – look great with them. And the block heel makes them just right for tights and skirts or dresses, too.
Fit Tip: They run true to size.
Alternatives: They come in a pretty burgundy suede through the ‘shop it’ button, too. If your size is sold out through the ‘shop it’ button at Nordstrom, Zappos also carries it. STEVEN has a similar version without any metal hardware.

Cocktail Party Chic.
Why is it a Find? From Banana Republic, this awesome red dress is selling out quickly, and we certainly understand why. Not only is it on sale, it’s super flattering. The pretty shade of red looks great on most every skin tone, and really speaks to the holiday season. The fabric has nice weight to it, and it’s fit-and-flare styling shows off your waist, and effortlessly conceals your hips. The scalloped neckline equally flatters, without dipping too low. And our favorite hidden feature? The pockets. They don’t add bulk, but boy are they practical when you’re holding a drink and plate.
Wear it with: Banana Republic shows this dress with bare legs and nude strappy heels., and any metallic heels can create a similar look. Alternatively, we’re creating a look here around a more cold weather friendly way to wear this dress. Since we’re based in Chicago, we know bare legs and open shoes aren’t always the most practical way to head off to a holiday party. And quite frankly, we just love the modern look of deep and saturated black legwear with bold red – especially for the holidays. With color blocking being such a trend this season, adding solid black accents to this rich red dress is the perfect holiday way to interpret it.
Fit Tip: Banana Republic’s fit is modern and not too trim. This dress comes in Petite and Tall as well, so the scalloped hem won’t need to be altered. The length looks great from mid-thigh to just above the knee. (And shorter ladies, if it’s still too long because your Petite size is already sold out, any tailor can shorter it from the straps, too.) The body isn’t too trim and the fabric has some stretch to it, so if you are often between sizes, you can go with your smaller size.
Alternatives: This dress comes in always appropriate black through the 'shop it' button, too. Prefer a sleeve? Eliza J’s dress has that and more - a pintuck waist detail and flared skirt ensure it highlights your best assets – the green and black color options are our top picks. And David Meister’s vibrant blue alternative stuns in its simplicity and ruffled cuff on its long sleeves. But you can stick with red, as we’re featuring, by choosing Taylor’s ¾ sleeve, fit-and-flare option. If you are looking for a feminine, contemporary style, Cinq a Sept’s ruffled LBD is our absolute favorite - perfect all the way through New Year’s Eve.

Why is it a Find? The scalloped neckline of the featured dress doesn’t need much, but we can’t resist the jet black stones of this necklace to add some truly modern-looking sparkle.
Wear it with: We love the way this necklace looks on its own – and we doubly love wearing two of them together for a chunkier look. You can’t go wrong either way. When you’re not wearing it with a cocktail or formal dress, it’s so pretty popping out from inside your button down shirt or highlighting the neckline of a simple sweater or date night top.
Fit Tip: It has a 17” length (and can be adjusted 3” longer) so it’s not too long – great for the neckline of the dress to the left. Click through the ‘shop it’ button to see how looks on in the alternative images.
Alternatives: Instead of sparkly stones, a chunky, black acrylic floral bib necklace or an oversized black link collar necklace will add bold style and play up a wonderful contrast to the saturated red of the featured dress.

Why is it a Find? Like we said, our hometown of Chicago always has us thinking of ways to stay warm when we dress up during the holidays. And a faux fur stole is a fashionable way to do it.
Wear it with: If it’s seriously cold out, you can even drape this stole around your coat, like an oversized scarf. When you get to the party, ditch your coat and keep this on for a stylish finish with the featured red dress. Click through the ‘shop it’ button to check out the alternative image where Nordstrom even shows how you can wear it belted over a top.
Fit Tip: The longer length will easily wrap around your shoulders and hang to about lower hip/upper thigh on most ladies.
Alternatives: We are featuring this faux fur, but you can also go with the real thing in this black rabbit fur scarf. You can further embrace the fur trend with this black rabbit capelet that is just as chic with the featured dress as it with jeans, a tank top, and heels for a casual holiday night out.

Why is it a Find? We’ve been talking about how chic this red dress looks with rich, black accessories and these kate spade new york ankle strap suede heels are just what we had in mind.
Wear it with: Saturated black legwear – not sheer – play up the modern contrast of color, and these Commando tights are without a doubt, the best. They don’t bind at the waist, and have a really saturated color that holds up after multiple wears.
Fit Tip: These run true to size with an almond-shaped toe and 3 ½” heel that feels quite wearable with the security of the ankle strap.
Alternatives: These pumps come in some other pretty colors through the ‘shop it’ button, too.

Your Holiday Finest.
Why is it a Find? Ladies, this Tahari dress plays off tuxedo styling in the most feminine and flattering of ways. Just as pretty in person as it is in this picture, we know it’s not easy finding a dressy dress that isn’t sleeveless or strapless. So whether you don’t like to show off your arms, or you just want something seasonally appropriate for that upscale holiday party, this dress is the answer.
Wear it with: The pretty portrait neckline shows off your collarbones, which is so slimming, so we recommend keeping the jewelry to a minimum as you’ll see in this outfit. The ruched bodice creates an incredibly slimming line (ideal to conceal a few extra holiday snacks) and adds interest that really allows the dress to stand on its own.
Fit Tip: The modern fit, in sizes 2-16, runs true to size.
Alternatives: Not only does it come in red or green through the ‘shop it’ button, it comes in an awesome velvet version, too. And, of course, the velvet options don’t end there this season. T Tahari has a velvet faux wrap style that has a modern fit and is so pretty with added festive touch of a sparkly belt. If you need a full length gown, Alice+Olivia’s stunningly simple long-sleeve, contemporary-fitting black dress has a knot detail that truly flatters and conceals, while David Meister’s modern-fitting navy version has a ruched waist detail that creates the same gorgeously flattering results.

Why is it a Find? To ensure your jewelry doesn’t interfere with the neckline of the featured dress, these kate spade new york studs add some sparkle in just the right way. They are bold enough to be seen, even with your hair down, and the wine-colored purple/red crystals adds a festive vibe without being too literal.
Wear it with: With the dress shown, a beautiful silk blouse, or a lovely cashmere sweater, these statement earrings will add style to anything. And on sale, you can’t go wrong.
Fit Tip: Click through the ‘shop it’ button to get a better sense of the size in the alternative image on model.
Alternatives: You can also keep things more classic with silver, gold, or even pearl and crystal earrings.

Why is it a Find? Building on a chic color accent to the featured black dress, these Sam Edelman pumps are such a pretty shade of deep purple/red – much like your favorite glass of red wine (and the earrings above).
Wear it with: Velvet pumps are a perfect in a dressy look, like we’re showing, and the color is dark enough to look just right with sheer black hose. They look equally great with simple black pants or jeans, too, so don’t forget about them when you’re getting dressed for a date night or drinks and dinner with girlfriends.
Fit Tip: They run true to size.
Alternatives: These shoes come in tons of colors and patterns, including black leather and black suede, which will both look great with the satin of this dress. And for a true holiday look, add J.Crew’s black watch plaid heels, tartan plaid block heels, or stewart plaid pumps.

Why is it a Find? This Shiraleah velvet clutch is a very well-priced option that packs a lot of holiday style, with its stylishly oversized bow. You can find similar bags at much higher price points, but for an accessory like this, you won’t beat the quality of this option.
Wear it with: The pretty bow detail really lends itself to the collar detail of the dress, and will add instant holiday fun to any outfit – even jeans and a cute blouse when you’re meeting up with friends for drinks.
Fit Tip: It is big enough to hold your phone (even your iPhone 6 or 7 Plus) and your other essentials.
Alternatives: You can continue on the purple/wine accent color we’ve shown in the shoes and earrings, by going with this eggplant colored velvet clutch. But don’t feel like you have to match all of your accessories - and they also don’t need to match each other exactly, if you do choose to stick with one accent color.