T Shirt Dress Outfit

35 Best T-shirt Dress Outfit Ideas for Midsize Women

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T-shirt dresses have become one of those go-to wardrobe staples. 

As someone who has a hard time finding dresses that work for my small top and larger size 12 bottom, when I find one with an A-line shape, the t-shirt dress is something I can actually wear.

Resembling oversized tees, there are so many easy ways to wear them casually, for date nights, and even for work.

The t-shirt dress is a straightforward dress that skims the body. It comes in a rounded crew neck or V-neck. With short sleeves or long sleeves. And in a variety of lengths, from a mini hitting at the thigh, to knee-length, to a midi-length below the knee, or as a maxi shirt dress. 

It may also have tiers at the bottom, dressing it up a bit more. 

This dress comes in tons of different colors, and in everything from striped, to a white shirt dress, to black, and a variety of solid colors in between.

It doesn’t have to just be a summer dress. You can make a t-shirt dress work for fall by wearing it over a pair of black leggings or with a light wash jean, if that feels like you.

Top it with a classic trench coat, a denim jacket, a utility jacket or a leather jacket. 

A cousin of the t-shirt dress is the shirt dress. It resembles an oversized button-down shirt. You’ve probably most often seen it as a denim shirt dress. 

There are so many different ways you can wear the t shirt dress and shirt dress. 

If this is your first time wearing one, or you’re just looking for new ways to wear it, I have 35 t-shirt dress outfit ideas for you! I’m using dresses with more of an A-line shape that work for larger bottoms.

Let’s start with a solid t-shirt dress. 

Solid t-shirt dress

Pair your t-shirt dress with your favorite shoes and add a leather bag. Belt bags are a cute option to add some waist definition, if that feels like your style.

It’s a great idea to wear a pair of biker shorts underneath to prevent thigh rubbing. As a size 12 with larger thighs, I wear them with all my dresses. 

Let’s look at easy casual outfits.

Casual outfits: Olive t-shirt dress

This olive t-shirt dress is from Amazon. If you buy one, air dry it laying flat to maintain it’s shape.

Let’s look at how to style it.

1. With nude leather flip flops and a tote bag

I love how it has a bit of an A-line shape. It’s flowy and not clingy in all the right places, which works if you’re larger on the bottom. I’m wearing it in a size large.

2. With a baseball cap, gray sweatshirt, and gray Birkenstock clogs

Have you tried Birkenstock clogs? I saw an article the other day that said they are starting to have a moment. It was an experiment to try them with this dress. I think it’s got a casual cool vibe.

I’d wear this to the grocery store for sure!

3. With black Adidas and a black hooded sweatshirt tied at the waist

4. With black Gizeh thong Birkenstocks and a dark blue jean jacket

Okay, next lets look at outfits for work with this dress.

Work outfits

5. With brown Mia clogs, a coordinating brown bag and dark blue jean jacket

6. With black flats, a black tote bag and black blazer

7. With clogs and a crossbody bag

8. With brown wedge ankle-wrap sandals and a brown bag

9. With black ankle-wrap sandals and a black saddlebag

Okay, now let’s look at another solid t-shirt dress. This one is black.

Casual outfits: Black t-shirt dress

This t-shirt dress is a bit A-line and has a bit of swing to it with a tulip sleeve. Here are 4 ways to wear it casually.

10. With black Adidas tennis shoes and a black hooded sweatshirt tied at the waist

11. With a black ankle-wrap sandal and a black leather tassel necklace

12. With a plaid flannel shirt tied at the waist and black Adidas

Work outfits

13. With animal print ballet flats and a black crossbody saddlebag

Black T Shirt Dress Outfit

14. With black flats and a black blazer

15. With Mia clogs and cognac colored cardigan sweater

Black T Shirt Dress Outfit

This cardigan is reading as very orange in the picture but it’s actually more the color of the shoes. A cognac or cinnamon color.

It looks very chic paired with black.

16. With tan and black cap toe shoes and a black blazer

Black T Shirt Dress Outfit

Next up, date night outfit ideas.

For date night

17. With a simple nude kitten heel sandal and mother of pearl necklace jewelry

Black T Shirt Dress Outfit

18. With a black heel and a short black tweed jacket

Swap this out for a leather jacket if that feels more like you. 

19. With brown wedge ankle-wrap sandals and a bag

Black T Shirt Dress Outfit

 This dress is so versatile, I’ve even worn it to a funeral.

20. With black tights and black ankle boots and a black blazer (not pictured)

Just make sure your black ankle boots fit tight at the ankle!

A knee-length tiered t-shirt dress

Let’s talk for a sec about dress lengths. 

At 5’6”, a maxi dress often feels too long for me. I feel like I’m being swallowed up by all that fabric. 

I lean towards a midi-length dress that hits below the knee. 

Or a knee-length dress like this one.

Casual outfits: Striped t-shirt dress

With knee-length you can wear it for dressier events like a baby shower or even church without dealing with all that excess fabric. 

Isn’t this a cute t-shirt dress? It’s from Amazon and has pockets. I love the stripes!

Striped Tiered T Shirt Dress Outfit
Outfit details: I’m wearing this dress in a medium and it fits TTS. 

Let’s look at how to wear it!

21. With a pair of white sneakers and a crossbody bag

The blue and green striped strap coordinates with the green in the logo of the Tretorn tennis shoe to bring in another pop of color. 

22. With leather flip flops, a jean jacket, and a blue and green strap crossbody bag

For work

23. With black flats and a blue blazer

Okay, let’s look at another striped t-shirt dress. This one has a tie at the waist.

Black and white striped tie waist t-shirt dress

This staple J.Crew Factory t-shirt dress works for women with smaller tops and larger bottoms, like I have. And if you have a larger bust, according to the reviews, this dress also works for you. 

The stripes move the eye around and the attached tie at the waist magically minimizes the pooch of a softer stomach. It’s such a good dress, they sell it year after year.

Here are 6 ways to wear it

Casual outfits: Striped tie waist t-shirt dress 

24. With black Adidas tennis shoes

25. With a pair of white sneakers, jean jacket and colorful camera strap bag

26. With leather flip flops and a similar tone tote bag

Striped tie-waist T Shirt Dress Outfit

27. With a leather flip flop, jean jacket and tote bag

Striped tie-waist T Shirt Dress Outfit

For dinner out

28. With a black ankle-wrap sandal and fun tapestry bag

For work

29. With a blue blazer and black flats

Okay, now let’s look at this blue chambray striped shirt dress

Striped shirt dress

This dress from Amazon has pockets! It comes with a waist tie but I like it better without it since it has a tier at the bottom.

Casual outfits: Striped shirt dress

30. With nude leather flip flops and a crossbody bag

Striped Shirt Dress Outfit
Outfit details: This dress fits oversized. I’m wearing a medium.

31. With a pair of white sneakers and a blue and green striped strap bag

Now, let’s look at just one more dress! This is another shirt dress. This was from Loft and has pockets!

Olive green shirt dress

As soon as I saw this dress, the fabric screamed date night. It’s a bit of a heavier weight and has a bit of a sheen. 

Here are 4 looks with it.

32. With a brown wedge ankle-wrap sandal and a brown crossbody

Shirt Dress Outfit

33. With a black ankle wrap sandal and a black saddle bag

34. With a tan leather flip flop for an easy breezy look

35. With a brown suede kitten heel

Shirt Dress Outfit

This color looks amazing with cognac brown.

The magic of the t-shirt dress

If you are larger on the bottom, look for a t-shirt dress with a bit of an a-line shape.

Once you find one that works, there are so many easy ways to wear it!

It will become a wardrobe staple.


Hi, Friend. I'm Marya. I'm so glad you're here!

I’m here to help women feel good inside and out through approachable everyday style inspiration and encouragement for midlife. Once upon a time, I worked as a therapist and coach. Now, I’m a holistic style blogger studying style coaching! Be So You celebrates leaning into who we were meant to be! 

Read about my  journey to self-discovery at 40. Follow me on Instagram here and Pinterest here. Send me a quick question through my contact page here.  

Fit Note: I’m midsized at 5’6″, 160 pounds, with size 12 jeans.

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