How to Wear a Sleeveless Dress All Year Round

Whether you have toned upper arms like Michelle Obama or have a double wave when you wave goodbye, sleeveless dresses are an item you can wear not just in the Summer but also as a transitional Fall item. With Summer slowly kissing us goodbye, you don’t have to stow away your sleeveless dresses just yet.

Although your bare arms might not be on full display, there are multiple ways you can still style your favorite sleeveless dress for the colder weather. Think layers, jackets, light sweaters and longline cardigans.

If you’re interested in seeing different ways you can create sleeveless looks year round, do keep reading!

During the summer months, it’s so easy to just grab a sleeveless dress or top and wear to practically anywhere but most people draw a blank when it comes to styling the same item when it’s colder outside.

In today’s post, I will start off by showing you ways to wear a sleeveless dress in the warmer weather and then proceed to give you some major style inspiration for styling the same sleeveless dresses in the Fall. I will be ending at Fall because the Canadian winter can be pretty brutal and most people would not be reaching for a strapless dress when it’s -30 degrees outside!

If you’re blessed with milder weather during the winter months then you can definitely pull off some of these looks during that period.

*Do note that this post would be focusing on styling sleeveless tops and dresses when you do not wish to wear them as is. This might be because you’re insecure about your arms, usually due to some loose skin, and consider them a problem area.

*Disclosure: This post may contain affiliate links, which means that I get a small commission if you decide to make a purchase through the links, at no cost to you.

A) Going sleeveless in the Summer

1) Wear a white tee underneath

In my recent post on how to wear maxi dresses in the Fall, I talked about how a great option for taking a maxi dress into the Fall is by placing a white tee underneath. This theory can once again be applied here. A white tee is something we can all find in our closets, making this look very easy and affordable.

Get a similar look HERE

Image from Here

The shorter sleeves on the t-shirt would allow you to still stay cool in the summer heat while the whiteness of the shirt would mean it could be paired with dresses in different colors and prints thanks to its neutrality. It’s a win-win situation.

2) Add a sheer top or cover up

On hot days, sometimes you want to show some skin without risking tan lines or sunburns. Here is where a sheer top or cover up comes into play. You can just drape the cover up across your shoulders and you would be covering your arms while still allowing the beauty of your décolletage to show. This would elongate your neck, and instantly make you appear sexier without even trying.

Get a similar look HERE

A sheer top or cover up is also a great way to go if you wish to wear a sleeveless dress on a date but worry about the dress code of the restaurant or if you think you have flabby arms and feel insecure about them. Sheer fabrics are more on the elegant side and so are a good idea to pair with your strapless dresses for more formal events.

3) Throw on a cropped jacket

Cropped jackets with either a short sleeve or long sleeves are an easy way to style your sleeveless dress when you’re not feeling up to baring your beautiful arms. They also work very nicely during the chillier summer evenings. The jacket could be a jean jacket, a utility jacket or any other jacket that won’t overwhelm your more feminine look.

Image source Here

A cropped jacket hitting you right at the smallest part of your waist would flatter it very nicely, especially if your sleeveless dress is more form-fitting. The best part about adding a jacket on top of your dress is that you don’t have to worry about your bra strap because it would be hidden underneath, shh.

4) Add a tied up denim shirt

A denim shirt makes an outfit a little bit more casual and allows you to not show as much skin with your strapless look. I personally prefer tying my denim shirts into a cute knot in the front whenever I’m wearing them with a skirt or dress. It makes my overall look more flirty and fun.

Get a similar shirt HERE
Image source Here

A pair of white sneakers (these are highly reviewed) is always a great look when denim is involved and so feel free to really amp up the casual vibes by making them your footwear of choice. If this look is for date night, you’re more than welcome to swap the sneakers for some high heels.

B) Wearing a sleeveless dress in the Fall

1) Add a denim jacket

Now that we’re in the Fall territory, it’s time to keep our bodies a little bit warmer with our sleeveless dress looks. Although the hot weather may be gone, you can let your strapless dresses make a Fall appearance by pairing them with your favorite denim jacket.

Image source Here

I’ve said many times on this blog that a denim jacket is a wardrobe staple and I invite you to invest in a great one if you have not already. It will take you across seasons and years. No matter your body shape, a denim jacket can make you look cool and more youthful when paired with a sleeveless dress. Utility jackets could also work if you don’t happen to own any denim jackets.

2) Wrap yourself up in a trench coat

Another Fall wardrobe staple I have talked about before is the trench coat. A trench coat. would be the perfect choice of outerwear to go with your sleeveless dress if you’re going for a function that requires a business formal dress code. I’m really loving this classic one HERE.

Image source Here

With its midi length and belted waist, the trench coat is a jacket that flatters all body types, regardless of whatever you got going on underneath it. You could literally get away with wearing your pajamas to the store if you had a trench coat over them. This look would work great for a night on the town as well, just complete it with a pair of heels.

3) Wear a drapey cardigan

Drape collar longline cardigans such as this one are my favorite type of cardigan for this look. You can create a very stylish look by adding a longer cardigan to your sleeveless garments and then adding a small belt on top of it. You don’t need to have the perfect body to pull off this look because the belt would already be cinching you in and accentuating your curves. This is a look you could take from the office to the grocery and even to the library and you would be comfortable yet chic.

Image source Here

For a more casual look during the summer, you could opt for a sheer cardigan. During the Fall, stick to a thicker material for extra warmth. If you want to appear to create a new look with an old strapless dress, this would be the easiest way – all you need to do is choose different colors of cardigans!

4) Place a sweater underneath

Another tip I previously shared on my post where I gave tips on how to wear maxi dresses in the Fall is the sweater underneath the dress trick. If your dress is made from a lighter material, I suggest opting for a thinner cardigan/sweater. This is to avoid looking unnecessarily bulkier. If you own only chunkier sweaters, I suggest wearing your sweater over your sleeveless dress or top.

Image source Here

If your strapless dress has a thicker strap, you may want to go with a sweater in a darker color such as black – this would give the illusion of smaller arms and a generally smaller frame. A shorter cardigan with buttons could also be worn on top of your dress for a more formal and dressier look. Keep the cardigan unbuttoned to show off most of the dress and hide just your arms. This is especially great if your dress has a deeper cut – va va voom.

5) Throw on a leather jacket

You know I could not complete this list without having a leather jacket on it. I cannot emphasize enough how important it is to own a good quality leather (or faux leather) jacket. Just like the denim jacket, it carries you across seasons and decades however, it gives you a more sassy and sexy vibe versus a denim jacket. Think of it this way: denim is more casual while leather is more polished.

A moto jacket might be the most versatile piece of clothing in your wardrobe and so you want to get the most out of it. You probably already own one and if you spent some good money on yours, then you should be getting your money’s worth.

Image source Here

While we’re on the topic of leather jackets, don’t sleep on brown leather jackets as I described in this post. I know most people’s instinct is to get or reach for a black leather jacket but a brown one is just as easy to style and could compliment your skin even more. Sometimes, the black might be a little too much, especially if your dress is in a lighter color.

I hope you’ve gotten some great ideas for how next to style your sleeveless dresses, especially if you’re insecure about your arms. Remember that the perfect option for you might not necessarily work for the next person as our style is based on our body type, skin type and personal preference.

I would also like to say that sagging skin is a natural process associated with aging. I understand some of us may be insecure about showing our ‘flabby arms’ in public and as we get older, we tend to show less and less of our aging bodies. Don’t let this weigh on your mind or prevent you from living your best stylish life. After all, we only get one shot at this thing called life 🙂

Until the next post,