How to Rock an Ugly Holiday Sweater in Style: Crazy, Conservative & Cool

by Sammy in Comment — Updated April 6, 2020

The Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good Causes

HAPPY FRIDAY!!! With Friday comes the weekend … and with the weekend comes sleeping in, brunch and … HOLIDAY PARTIES!!!!!

And if you’re anything like me and feeling the real mood of the holidays, you’re ready to embrace all elements of the holiday’s style mood, too. Including — but certainly not limited to — wearing an UGLY HOLIDAY SWEATER! to your next seasonal soiree.

Whether that soiree is costume-themed or not, wearing a holiday-themed sweater — whether it’s ugly OR pretty, it’s up to you — is the perfect way to embrace your personal style in confidence and to attract new people, new conversation and new FUN the next time you’re in a room full of strangers with only a punch bowl and some egg nog between you.

But the question remains: What IS an ugly holiday sweater, and who defines what “ugly” is on a sweater of this kind, anyway? I found myself asking that question as I thrifted ugly sweaters at a Goodwill in my last YouTube video. I asked fellow thrifters for their opinion: Which one did they think was the ugliest? The pseudo ugly sweater expert in me would say that the sweater has to demonstrate a majority of the following qualities …

1.) holiday related design [snowmen, Santa, presents, snow, Christmas trees, sleds, etc.] 2.) Busy and highly visually stimulating holiday related design 3.) contrast of colors, outrageously bright colors or outright random colors 4.) decorative elements like sequins, patches, fur, etc. 5.) big buttons, plastic zippers, grandpa collars and cuffs 6.) remain slightly baggy on girls, i.e. no true flattering “silhouette” to sweater 7.) in a nutshell, the sweater makes anyone on the street give you a “second glance”

There are clearly many ways to judge an ugly holiday sweater — and in the end, it’s really subjective to the standards of your personal tastes. So, instead of limiting myself to just ONE ugly sweater, I bought three … and styled them in crazy, conservative & cool styles below. I wanted to prove that you can wear ugly holiday sweaters in style — and not just mockery of the sweater’s more …. er, how do I say this? “Liberated creativity” side.

Still, you’ll see in the vid and in the shots below that these sweaters, while ugly at first glance, actually look … GOOD! I’d love to hear your comments on which one is your fav and how YOU’D style it if you were its lucky owner. Don’t have an ugly sweater of your own? Visit the Goodwill store finder online and plug in your zip code to find the closest one near YOU! Then go thrift in holiday cheer and snag up a sweater like these for a bargain you definitely won’t want to exchange after Christmas.

I hope everyone has something planned for the weekend! And if it involves a holiday sweater + pictures, please email me a digital image of your fun holiday look! Holler at me [email protected] & @sammydvintage on Twitter!

xo, SD

p.s. Do you celebrate Hanukkah? Well guess what! You can wear ugly holiday sweaters TOO! Check out this awesome one a Sammy Davis Vintage facebook fan made herself!

Ugly Holiday Sweater Exhibit #1: CRAZY

The Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good Causes
The Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good CausesThe Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good Causes

The Sweater: Bright, busy and bulky — this is a holiday sweater more fitting for your crazy Aunt than you. Look past the corny cartoon snowmen and embrace its potential for low-cost holiday cheer.

How-to Accessorize It: When wearing bright, be bright. Pair this winter blue with cold weather staples in a contrasting color. Shown here: pink leggings, leg warmers and knit hat. I accentuated the sweater’s sequins with earrings that shine and quintessential winter gear, like these UGG boots and fur hat.

Where-to Wear It: Enough fun to rock at an ugly holiday sweater party, or to brighten a shadowy ski lodge over hot chocolate.

Ugly Holiday Sweater Exhibit #2: CONSERVATIVE

The Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good CausesThe Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good CausesThe Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good Causes
The Sweater: A buttoned-up version of a Christmas tree — presents not included. Nothing beats wearing sequin studded snowflakes on your sweater — that is, except the real thing itself: snow!

How-to Accessorize It: Keep this sweater’s faux fur more chic than fake with crystal or pearl jewelry, a bowed beret and a ribbon belt to comfortably cinch extra sweater for a feminine waist.

Where-to Wear It: When paired with heels and demure accessories, this look has enough class to wear for cocktails with a cutie. Switch pumps out for ballet flats, and you’ve got a look that works for day — think class or casual Friday at work.

Ugly Holiday Sweater Exhibit #3: COOL

The Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good CausesThe Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good CausesThe Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good Causes

The Sweater: If the holidays are about spreading the love, this sweater’s got the right emotion — and then some, just for extra measure. Sure, it’s more stimulating than your neighbor’s over-the-top light display, but when styled with solids, this sweater isn’t so bad — actually, it’s kind of cool.

How-to Accessorize It: Most ugly holiday sweaters resemble this one, with enough patterns to keep a toddler’s attention deficit disorder at bay. Tone down the sweater’s multiple patterns with solids in blacks, whites or grays to help simplify the look.

I cut tears in old black leggings and wore them over festive fishnet tights to add an extra level of warmth. A studded belt and stiletto heels add rocker edge that I balanced with a girly flower clip and modern gold hoops and bangles.

Where-to Wear It: If Kris Kringle invited you to party, this would be the perfect outfit for the dance floor. It’s a seasonally sexy look worn best past midnight and never forgotten if spotted beneath some mistletoe.

The Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good Causes

How to Rock Your Ugly Holiday Sweater in Style*

The Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good CausesRight now, your local thrift store is sitting on a treasure trove of ugly holiday sweaters just waiting for you to wear them ironically.

Whether you’ve got a holiday theme party to attend or you’re just looking to celebrate the season in high cheeky fashion, wearing an ugly holiday sweater is a fresh way to have fun without depleting your savings account for all those gifts you have (yet) to get.

It’s not easy looking good in a sweater with enough flare to rival the uniform of a TGI Friday’s waitress. So here’s some advice on how to wear an ugly holiday sweater in three unique ways and for many merry memories you won’t want to exchange for style credit.

The Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good Causes

Three holiday sweaters purchased at a Goodwill thrift store, each offering a unique style challenge. Each sweater cost $4 — but the seasonal style return? Priceless.

Ugly Holiday Sweater Challenge #1: Crazy

The Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good Causes

The Sweater: Bright, busy and bulky — this is a holiday sweater more fitting for your crazy Aunt than you. Look past the corny cartoon snowmen and embrace its potential for low-cost holiday cheer.

How-to Accessorize It: When wearing bright, be bright. Pair this winter blue with cold weather staples in a contrasting color. Shown here: pink leggings, leg warmers and knit hat. I accentuated the sweater’s sequins with earrings that shine and quintessential winter gear, like these UGG boots and fur hat.

Where-to Wear It: Enough fun to rock at an ugly holiday sweater party, or to brighten a shadowy ski lodge over hot chocolate.

The Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good Causes

Ugly Holiday Sweater Challenge #2: Conservative

The Fur Debate: How to be Sustainable & Recycle Vintage Fur for Good Causes

The Sweater: A buttoned-up version of a Christmas tree — presents not included. Nothing beats wearing sequin studded snowflakes on your sweater — that is, except the real thing itself: snow!

How-to Accessorize It: Keep this sweater’s faux fur more chic than fake with crystal or pearl jewelry, a bowed beret and a ribbon belt to comfortably cinch extra sweater for a feminine waist.

Where-to Wear It: When paired with heels and demure accessories, this look has enough class to wear for cocktails with a cutie. Switch pumps out for ballet flats, and you’ve got a look that works for day — think class or casual Friday at work.

1 thought on “How to Rock an Ugly Holiday Sweater in Style: Crazy, Conservative & Cool”

  1. You pulled this off so well. When I saw the title, I was thinking…”How can she make a holiday ugly sweater cool, conservative, crazy?” lol But you did it. I loved the conservative one the most and Cool next. Thanks for sharing

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