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How to style dresses

shoppingisfun

(website)

Veteran

Well after spending all day shopping on Wednesday and finding only one pair of mediocre jeans, I've decided to incorporate dresses into my wardrobe. The problem is I have no clue how to wear them for fall. Let's say I'm wearing a black jersey dress. Can I wear leggings? Tights? What kind of shoes?

My work is casual and people wear everything from sweats to suit separates. So anything goes as far as formality/casualness. I just don't even know what's trendy.

Pics of examples are appreciated. Thanks!

Dressing

18 replies

Latest reply was from shoppingisfun

rachylou

Veteran

Gosh! So many options! Any particular kind of dress in mind? Longer hemlines are trending...

Angie

(website)

Fashion Stylist

It really depends on the dress. Perhaps you could provide a link of the dress, and we can help you style it.

shoppingisfun

(website)

Veteran

Here are some examples. If it helps I'm 5'1 and about 125 lbs, somewhere between an hourglass and a pear.

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shiny

Veteran

For dresses like those I'd get some tall boots. Pop some warm socks underneath and you may be warm enough with bare legs, or you could do nude pantyhose.

You could also do booties but in the Fall I like more of my leg covered.

Gretchen

Veteran

+1 for tall boots. If you are going to be too cold, you could do tights+ boots or booties.

Also, consider if you will need a topper in the office. I tend to run cold so even on dress days I've got a sweater or ruana with me just in case. This can also help if you want a more casual look.

Sara L.

Veteran

I think dresses are the easiest thing to style because they don't need anything except shoes and some jewelry. As the weather gets cooler you can add layers like a cardigan/jacket and tights. I wear boots without tights in the early fall and then add tights as it gets colder. I like fleece lined tights for winter which are a bit thinner than leggings. Leggings can work too though. I also start adding scarfs as the weather cools down.

shoppingisfun

(website)

Veteran

Thanks for the responses. Is it okay to wear black tights with a black dress? It seems like a lot of black.

As for boots, I am sadly lacking in the area of ankle boots. I do have a pair of low-to-mid-calf black Moto boots, and a pair of similar gray boots. I also own a pair of tall black leather boots. Ugh I need new shoes.

DonnaF

Veteran

We are the same height and close to the same weight and shape. Below are some of my dresses. The first three are regular (vs. Petite) size, so they hit me a bit longer than the stock photos indicate. The first is heavy denim and the second and third are sweatshirt material. The black and white check is flannel.

For the sleeveless dresses, I add a shirt or t-shirt, or turtleneck underneath.

I would wear tights or cropped jeans or pants under all of them. Tights can stick to certain fabrics, so I also add a half-slip to combat the cling and for warmth. I have recently added patterned fishnet type hose to wear when it is too cool for bare legs but too warm for tights.

I don't wear tall boots because my weather is mostly too mild and my short muscular legs and fussy feet are too hard to fit. Others can talk to you about footwear.

Free People Free People Wandering Star Denim Minidress | Nordstrom

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Gibson Gibson Pleat Back Minidress | Nordstrom

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Caslon Off-Duty Hooded Sweatshirt Dress

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Sanctuary Sadie Rib Stripe Dress

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Madewell Latitude Check Shirtdress

Sale

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Halogen Flounce Back Shift Dress

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6

Hue Metallic Fishnet Tights

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Commando Deco Fishnet Tights

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Large Rose Tights

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Chelsea28 Mini Geometric Net Tights

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shoppingisfun

(website)

Veteran

Thanks Donna! I wasn't sure if textures/lacy hose was still a thing or not.

Have you found a particular type of tights that are comfortable and don't rip easily?

I'm intrigued by the idea of fleece lined tights like Sarah mentioned. It seems like they would be stronger and more comfy...?

DonnaF

Veteran

I have no idea whether textured or lacy hose is In or Out; they just fill a particular temperature niche for me as I am very temperature sensitive. I live in California so have no need for fleece lined tights. I got a pair for my daughter in Chicago, and she likes/liked them. They really run the gamut in terms of price. I got her cheap ones.

In terms of comfort and wear: I usually size up in tights, especially if I am near the border between two sizes. Usually this works since I have heavy legs, but sometimes I end up with baggy legs since mine are also short. I rarely have the segmented worm feeling that many women complain about. Tights too small tend to crawl down and run more easily. I also never buy control top if I can help it as I hate, hate, hate them.

cindysmith

Veteran

I like dresses with tall boots. Now, what style of tall boots will vary for me based upon the dress. Some dresses seem to want to be paired with equestrian style riding boots, some beg for point-toe stilettos heeled tall boots, and a really boho type dress would say harness boot to me.

I have always lived in areas with mild winters, so I could sometimes get away with a dress, some pumps, and no stockings/hose just as if it were summer.

Bijou

Veteran

I wear dresses with nude hose and booties in cooler weather and will often wear a cropped jacket over them as a topper. I wear denim jackets for a more casual look and a tailored jacket for work. My jackets are in finds.

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Kate Spade New York textured tweed jacket

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Mainelady

Veteran

I’m loving the dresses this year and will change how I style mine as we move towards winter. Right now, flats or sneakers and jewelry work nicely. Soon I will change my footwear to booties and add lightweight cardigans or jackets. Next up will be to add tights. I will continue with tights and tall boots, heavier sweaters and jackets and also add scarves. I prefer fleece lined tights to leggings, unless it is extremely cold.
Have fun styling your dresses. I hope you will share some pics.

Jenni NZ

Veteran

I pretty much detest tights. So under my dresses in the winter I would often wear black ponte skinny pants and then socks, I hide the socks with tall boots or booties. If the pants are skinny enough they don't look that different to tights, in my book. I will wear tights occasionally with a pump type of shoe. But it's pretty much under protest. Hence prefer to buy booties.

lisaflex

Veteran

HUE brand has some really nice fleece lined tights that last. wash by hand hang to dry.

Anonymous

I wear Colored hose until tights are needed. Although I like the look on others- combining with leggings is not a great look for me. I do wear boots too.
Usually I will combine with cardi for casual or casual blazer for little polished look so as to not look too corporate. Most of my dresses are sleeveless so I need something.
Also use more scarves in cooler weather ( more jewelry in summer.

Becky

Veteran

Like others, I often wear tall boots with colored hose, then tights, then leggings as temperatures drop in the fall and winter. I prefer tights and leggings with a wider waistband so they are not noticeable under dresses. I have been known to wear dresses with colored hose and ankle booties if the weather is mild enough, but I run cold so this is not a usual look for me.

shoppingisfun

(website)

Veteran

Thanks for all the replies!
Bare legs don't really do it for me unless I'm going to be outside in the summer...I run really cold. I love the idea of fleece lined leggings or tights! I live in California and it does not get all that cold, but I am pretty much always cold anyway! Even in the summer, since the AC is generally blasting indoors.

I will be sure to post pics when my new dresses get here (assuming they fit and look decent in person lol).