Sweaters and Dresses: How to Wear Summer Dresses All Year Long

Fall is here and winter is knocking at the door, but that’s no reason to stop keeping your summer dresses top of mind. Layering your winter sweaters over your summer dresses is a great way to extend the life of your dresses and make better use of the clothes you already own.

The temperatures have dropped, the leaves have changed color, and the rain and snow will come. But while these changes usually signal that it’s time to put away your summer dresses to make room for jeans, coats, and other cool-weather clothes, they don’t have to! Spaghetti-strapped maxis, knee-length tank dresses, summer-night date-night dresses, and even cotton sundresses are so much more versatile than we give them credit for!

Here are six tips for how to layer sweaters over your summer dresses so that you can wear them all year:

 

Style Tip #1: Be Knotty

sweaters with summer dresses

As I mentioned last summer, I became a big fan of knotting tee-shirts and tanks over my dresses. Well, the same simple styling trick can be applied to knitwear.

The best and worst thing about winter sweaters is that they tend to hide our shape. Homo sapiens store fat in wintertime for survival and a cute-but-shapeless sweater can be a girl’s best friend when she gets a little thick in the middle after Christmas (am I right??)

But nipping a sweater in at your waistline can often create the illusion of curves and angles when those Sir Mix-A-Lot dimensions (36-24-26) start to look more like your kindergartner’s “find the pattern” math homework (38-38-38).

sweaters with summer dresses

sweaters with summer dresses

sweaters with summer dresses

What I’m wearing: Jersey Tank Dress by Madewell, Haley Leather Sandal by Vince, and the Jo Saddle Crossbody Bag in Black. The green fitted sweater by French Connection is not available, but try this one from Express or this one from C by Bloomingdale’s.  (Click here to see more of this look.)

This isn’t a good idea for your finer, more expensive knitwear. But for your more elastic and less expensive sweaters, it’s a good styling option.

Knot in the front which is easier, logistically, and can help camouflage a paunch, or in the back, which is harder to do yourself, but keeps the look cleaner from the front.

 

Style Tip #2: Fully Vested

sweaters and summer dresses

What I’m wearing: Black dot-print silk dress is by Presley Skye and not available, but try this one from DVF, black sleeveless turtleneck sweater is from Lou & Grey, but this one from French Connection is similar, suede wrap belt, Black Agnes Boots by Rag and Bone, and Jo Saddle Crossbody Bag in Black.

For your long sleeved dresses (which are so, so appreciated and yet SO, SO difficult to find), try layering your sleeveless sweaters over the top. This is an easy way to add texture, color contrast, or both to a look, as well as added warmth for those cooler winter days.

If the sweater is longer and try adding a belt in the same or similar color to create a taller, leaner look overall.

sweaters with summer dresses

sweaters and summer dresses

sweaters with summer dresses

What I’m wearing: Enza Costa Cashmere Dress, caramel-colored sleeveless sweater by Max Studio is not available, but try this one from Free People or this one from Vince, Ralph Lauren belt, lizard-embossed pumps by Elizabeth and James, and the Eva Tote in Cocoa.

 

Style Tip #3: Knits + Silks = Love

sweaters and summer dresses

What I’m wearing: Blue Cashmere Sloane sweater by Equipment, silk skirt by Max Studio and no longer available, but this pleated version by Jil Sander is similar, Banner NuBuck Sandals by Joie, and the Jo Saddle Crossbody Bag in Taupe. (Click here to see more of this look.)

In fashion, as in contemporary art, texture takes a look from good to great. I love the contrast of a fine silk skirt or dress with a nubby, fuzzy, or chunky sweater.

I tend to treat my silks with a little too much care and caution. As a result, I end up wearing them less frequently, which is a waste of both beauty and money. Adding a cozy sweater – even in a fine cashmere – takes the pressure off and lets me feel more relaxed and casual in my silk dresses and skirts.

sweaters with summer dresses

sweaters with summer dresses

What I’m wearing: Cream Sheridan sweater with gold threading from Splendid, silk leopard print dress from DVF is not available, but try this one from Raey or this one from MICHAEL by Michael Kors, Black Agnes Boots by Rag and Bone, and the  Jo Saddle Crossbody Bag in Black.

sweaters and summer dresses

 

Style Tip #4: Mix Wool Sweaters and Cotton Dresses

sweaters with summer dresses

What I’m wearing: Black Cashmere sweater by Equipment, black cotton dress by Sincerely Jules is not available, but this one from Rachel Roy is similar, Vince open-toe booties, and the Jo Saddle Crossbody Bag in Taupe. (Click here to see more of this look.)

Don’t be afraid to mix textures; even those textures you think of as “summer” or “winter” textures. Just like your silks, wool sweaters pair nicely with cotton or jersey knit dresses. The look is informal and relaxed, but still well put-together.

Choose monochromatic or like colors, patterns, and proportions to keep the look polished.

sweaters with summer dresses

sweaters with summer dresses

What I’m wearing: Gray Rosalie Slouchy Sweater by Elizabeth and James (which I am absolutely crazy about), black tank dress by Zara, but this one from Loves + Friends is similar, Adidas Originals Superstar sneakers, and the Jo Saddle Crossbody Bag in Black.

sweaters with summer dresses

Worried you’ll be too cold? Maslow’s Hierarchy of Needs trump everything else; no one should go through life cold and uncomfortable. If you pair your favorite winter sweater with your favorite summer dress and you’re still cold, consider Style Tip #5….

 

Style Tip #5 : Tights and Socks

Well, duh, right? But I’m not talking about about your daughter’s tights or your grandmother’s (or mother’s) pantyhose. I could (and should) publish and entire blog post on this topic alone. (Personally, I’ve been dying to try textured knee-high socks with pumps or heeled sandals and a skirt or dress, so stay tuned!)

Today’s tights come in hundreds of styles and colors, many of which can be layered and worn together. Try a nude fishnet stocking over opaque black tights for a polished and sexy take on winter hosiery or, for a more casual look, try a knee-high stocking over wool tights and booties.

layered stockings

Had it not been for the record-breaking heat wave this week, I would have happily modeled some tights and socks with my looks for you. However, to quote Samantha Jones from Sex in the City, the Movie, “I love you, but I love myself more” and I wasn’t willing to risk heat stroke for a good photo, so I pulled the above examples off of Pinterest. But I promise I’ll make it up to you.

 

Style Tip #6: Carry a Fabulous Leather Handbag


haerfest eva tote in cocoa

Of course, all of this is made much simpler by a fabulously beautiful and practical handbag, like these awesome bags from Haerfest (pronounced “harvest”).

I wish I could tell you how well-constructed and gorgeous these bags are. I love that I can fit my laptop into the Eva Tote along with my wallet, car keys, a water bottle, and all the other random mother detritus I have to store in my handbag at all times to get through the day. And I can’t say enough good things about the  Jo Saddle Crossbody Bag which doubles as a clutch for evening when you remove the strap. Between the beautiful gold hardware, the roomy-yet-sleek pouch, and the sumptuous color options, this just may be the closest thing to the PERFECT handbag!

haerfest jo saddle crossbody in taupe

haerfest jo saddle crossbody in black

haerfest jo saddle crossbody in taupe

Rethinking and reclassifying your summer dresses will double the breadth of your winter wardrobe and keep you looking chic and fresh all winter long!

Thanks for reading,

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9 thoughts on “Sweaters and Dresses: How to Wear Summer Dresses All Year Long

  1. Loved all the suggestions. I am going to go “relook” at my “summer” dresses right now and my sweaters. Thanks for the inspiration. Loved the Saddle bag too, many sold out!

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