Holiday Outfits in Your 50s and Beyond

Holiday Outfits in Your 50s and Beyond

It’s your 50th holiday season, or thereabouts, and you are well aware of the round of parties and get-togethers that you’re facing—we hope with joy! At the same time, as you have come into your own as a mature woman of substance, you know you’re not going to go out and grab a trendy fast-fashion dress that will only last this one season and you might be wondering what an ideal holiday party outfit for an attractive, vibrant 50-ish woman looks like now. What should you think about when dressing for holiday get-togethers, from casual girls’ night gift exchanges to fancy office cocktail parties? We can help you plan outfits that are stylish, appropriate, fun, and, as always, comfy!

Think About Your Needs

Are you hot all the time? Or cold? Do your feet get tired quickly? Can you simply not bear the idea of wearing a control garment to a dinner party? Consider what you, personally, need and want from your holiday party ensembles. If you overheat easily, consider a sleeveless dress with a cardigan or shawl so that you can regulate your temperature throughout the evening. The same goes for you if you run cold, but you might choose a warmer sweater dress as the centerpiece of your outfit, and wear thick tights for warmth rather than sheer hosiery. If you’re concerned about keeping your feet comfortable, remember that there are many evening shoes besides spindly stilettos. Check out kitten heels, trendy block heels, or supportive wedges if you really want some lift without sacrificing comfort, or look into velvet smoking slippers or glittery ballet flats for that little something extra in your footwear besides sky-high heels! Skip compression garments by wearing a pants suit or hosiery that will help your dress hang properly, and then you won’t need to skip the lasagna and fruitcake to stay comfy in your party clothes. Your needs must come first if you want to concentrate on connecting with people rather than your clothing, so prioritize that.

Think  About Your Style

One of the very best parts of maturing is learning about who you are and what makes you look and feel your best. When you’re planning an ensemble for a holiday party, remember that you are loved for yourself, and being yourself—even if this is a moment to be your best-presented self—is key to having a good time! If you literally never wear dresses, don’t start today! If you almost always wear boots, let’s plan an outfit that works with them. If you live in leggings, we can consider how to work them into a dressier, party-appropriate outfit. Don’t change your style to fit the occasion, because we have faith that you can make your style work for the occasion with a little thought and planning.

Take those aforementioned leggings. If you want to wear leggings to a dressy holiday party, consider getting some in stretch velvet, or wearing a pair with a tuxedo-stripe detail down the leg. You can pair these dressier leggings with a slouchy cashmere sweater or a long tuxedo jacket—the kind you wear alone as a top—depending on the kind of party you’re attending, and enjoy your evening in perfect comfort, feeling as much like yourself as you do on any other day. Your taste and style is worth showing off, just do it in a way that makes sense for the event!

Think About the Venue

We at Lands’ End are not big on “don’ts.” I am not here to tell you, “don’t wear a short skirt,” “don’t show cleavage,” “don’t wear graphic tees!” Part of the reason we’re not big on “don’ts” is that there is a time and place for everything! If your church women’s group is having their Christmas party at a bowling alley, a cute graphic T-shirt might be just right! If you’re going to a glitzy cocktail party with your spouse’s colleagues, a sequined cocktail dress that shows some skin might be perfectly appropriate! If you’re volunteering at a little one’s grade school holiday party, a themed Christmas sweater will probably be a big hit! These pieces are not dependent on your age or size, only where you plan to wear them and how you plan to style them.

I am big on propriety, as in, being appropriate. As long as you don’t mix up the ensembles you have planned for the cocktail party and the children’s party, you’re fine, although the children might get a kick out of it! I believe that grown-up women know best what to wear to help them look and feel their confident best, and simply encourage you to take that extra moment to consider time and place rather than silly “dos and don’ts.”

Ideas for Holiday Outfits in Your 50s and Beyond

·       People always seem to jump right to black for dressy parties and red for Christmas parties. Try building an ensemble around cream or “winter white.” It’s unexpected, flattering on almost everyone, and really lets your accessories shine. If you are lucky enough to have silver in your hair, this is especially beautiful.

·       Cape dresses are trending right now. If you’d like to try the trend without buying new, wear an appropriate strapless dress and pin a silk or lightweight cashmere shawl around your shoulders at the bustline—you can use matching or complementary brooches for flair. This look can help with thermoregulation as well as covering your arms if that is a clothing priority for you.

·       Try a “black tie creative” look, such as your comfiest old jeans with a silk blouse and sequined blazer or an evening dress with cute sneakers. Our society is at a fashion crossroads, where people are longing for glamor but loathe to sacrifice comfort. Help set a new standard that mixes what we most want!

·       Wear the accessories you love but never find occasion to wear. YOU are the occasion! If you have a fascinator, enormous cocktail ring, feathered evening bag or jeweled shoes you really love but never seem to wear, just do it! At best, you’ll feel fabulous and people will talk to you about your accessories. At worst, you’ll feel fabulous and people will talk to other people about your accessories, and there is no such thing as bad press.

·       Attend every gathering or social event with a good attitude and a smile on your face. Sometimes, especially after having been apart from society for so long, parties may seem like, well. . . too much. Remember that it is okay to excuse yourself for a breath of cold air or moment of quiet, and return ready to help make it a good time for everyone. We’re all a bit overwhelmed once in a while.

It’s Going to be Great!

Let younger women turn holiday parties into sartorial crises. You know your style, your taste, your frame and your figure, so knowing what to wear is easier than ever before. You have the experience to know what is appropriate, what everyone else will likely be wearing, and how to be comfortable and stylish at the same time. Holiday outfits in your 50s and beyond just get better!


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