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Winterize Your Outfit With a Sweater Dress

| Nov 12, 2018
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Winter is coming and it’s time to winterize our wardrobe with that great seasonal outfit…the Sweater Dress

A-line and straight shift sweater dresses

A-line and straight shift sweater dresses

To be honest, I don’t like the term “sweater dress.” For some reason, it sounds like a boring piece of clothing that a boring adult would wear, maybe in an annoyingly preppy way, and that image just isn’t appealing to me. But an actual sweater dress? I definitely don’t hate those and neither do many of us as you’ll see in our photos below.

A sweater dress is essentially a giant sweater that can be worn without pants, which is pretty amazing. They’re also perfect for winter weather  because they’re cozy and comfortable.

Stana and Teri Lynn in their sweater dresses

Stana and Teri Lynn Richards in their sweater dresses

Maybe you’ve always thought of sweater dresses the same way I do when I hear the term, and you’ve never tried them. Or maybe you have one and you have no idea what to wear it with. This clothing item is actually easier to style than you might think. Making them look good often comes down to picking the right sweater dress for you.

There are tons of options out there, and you have to pick the one that you like best on you. That doesn’t necessarily mean the most “flattering” option, it’s just the one YOU like the most. Want to know how to wear the coziest winter clothing item? Here are six ways to style a sweater dress., with cool outfit ideas from Fabulous After 40 that you’ll love and just by changing up your accessories and footwear, you get tons of mileage out of them:

Pair a Sweater Dress With Boots

Boots and sweater dresses go hand in hand to give you that relaxed, classy look. Tall boots are classic and elegant. Ankle booties are a little edgier and modern. Boots with a stacked heel complement earthy knits by adding balance. Suede boots look fab!

These slouchy black booties inspired by the ’80s are the hottest new boots around. Pair with this cozy red sweater dress with the asymmetrical neckline, this is a thoroughly modern mix! Check other these other ideas for wearing a sweater dress with boots.

sweater dress with boots

Crossdressers in sweater dress and boots

L – R Stana, Steffie Michaels

Belt It

Some knits are loose, straight up and down or rather chunky and hide your waist, so here’s an idea: try cinching in your knit dress with a beautiful belt. The chunkier the knit, the more substantial and wider you can go with the belt. Wear it around your waist or wear a wider belt loosely just at your waist on an angle towards one hip.

Add a scarf for visual interest (and warmth on those really cold days!), a pair of boots and a bag, and you’re done. The thing I love about all of these pieces is how neutral they are. They look great with this sweater dress, but they’ll go with everything else in your wardrobe.

-sweater dress with beltBelted sweater dresses

Tie on a Scarf

A solid colored dark knit sweater dress creates a slimming shape. Add a pretty scarf for texture and color and a shot of interest. Top off the look with booties in the same color as your dress and some accessories that pick up on the other colors in the scarf, and you have a sophisticated take on a cozy sweater dress.

tie on a scarf

sweater dresses with scarves

Wear a Sweater Dress with Leggings

Have you ever come across a sweater dress that you wanted to buy, but you thought it was too short?  Instead of passing it up, all you need to do is add a pair of black leggings to your outfit.  Leggings turn your sweater dress into a long top creating a look that is hip and modern.

sweater dress with leggings

sweater dress with leggings

Try a Cold Shoulder Sweater Dress 

This fall, a cold shoulder dress is hot! (I just couldn’t resist that one! LOL!) But seriously, cold shoulder styling is still a big deal so if you’re looking for a way to freshen up your sweater dress capsule, give serious thought to a cold shoulder sweater dress like this lovely burgundy one.

Cold shoulder sweater dress comb

Dress it Up

The finer the knit, the more formal the sweater dress and the easier it is to dress it up. This sleek and sophisticated cashmere sweater dress is already on the road to dressy. Add tall black leather boots, an elegant scarf and chic bag you have a stunning day outfit that totally rich, or the finer the knit, the more formal the sweater dress and the easier it is to dress it up. This sleek and sophisticated midi-length sweater dress is already on the road to dressy. Add heels, silver jewelry, and a ladylike clutch, and you’re ready for a special evening out.

sweater dress Dress it up comb

Actually, look at all the photos carefully because we have a wide range of looks that include scarves, statement belts, statement jewelry and killer heels.

Here are some other combinations you may not have thought about:

sweater dress with slip extenders

Sweater dress with slip extenders.

Sweater Dress for a Plus-Size Gal

We’re not all size 8-12 and in fact size 14 and up is considered plus-size. I’m a size 26-28 and want to feel good, as well as chic, in this wonderful dress, and yes, it’s possible.

Plus size CDs in sweater dress_


More tips on how to wear a sweater dress.


And your Winter Lookbook for styling chic sweater dresses.

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Category: Style, Transgender Fashion


About the Author ()

Tasi was a transgender, married, lifelong crossdresser. She passed away in late 2018. She’s the founder of the Ladies of the Blue Ridge transgender group in Roanoke VA, a prolific writer, commentator and blogger including fashion articles for Tri-Ess, TG Reporter, Repartee, and Pretty T-Girls magazine. Tasi currently resides in Merida, (Yucatan) Mexico. Her new website, Sister House and her blog, the Fashionable TG Woman are dedicated to fashion and style for the transgendered woman. Tasi’s book, "Top Ten Fashion Mistakes By Crossdressers and How To Fix Them" is available on Amazon or on her site free to subscribers.

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