How To Style An Oversized Shirt

An oversized shirt is one of my favorite close staples. It’s comfortable, it’s breezy and there’s so many ways to wear one no matter the season. It’s on constant rotation in my wardrobe all year round. I wanted to share some comfy and stylish oversized shirt outfit ideas so I’ve pulled together some looks with a tee, a cotton breton and a button down. All three of these have been in my wardrobe for a long time so I can attest to the fact that they are versatile and in my opinion, never go out of style. Here are some more tips and ideas for styling and oversize shirt.

How To Style an Oversized Shirt

pair a stripe button down with monotone bottoms

I love matching a stripe button down with bottoms, for example, a light blue striped button down with light blue leggings (see below) or a blue and white stripe button down with white trousers or jeans. I like how keeping it monotone looks chic and polished, whether you’re dressing up or more casual.

size up in a cotton breton

I’ve had my Saint James Meridien breton for years. I bought my first one in a little shop on Block Island 6 or 7 years ago and now I have three (I have the Meridame style in red and white). They are so comfortable, stylish and timeless. I usually go up a few sizes because I love when they’re slouchy and cozy.

layer it for cooler seasons

An oversized tee or button down looks super cool under a blazer. For cooler months try an oversized sweater or a chunky cardigan over a button down.

tuck it in

Sometimes I do a casual half tuck in the front with my oversized shirts. It gives them a little shape. You can also do a full tuck (see below) which I love with a high waist.

try a men’s tee

One of my absolute favorite tees of all time is actually mens. It’s slightly boxier, super soft, and looks perfectly worn. I usually size down in a men’s tee for a fit that’s oversized but not too big.

go for a classic white button down

You can’t go wrong with a classic white button down. Some styles are already oversized, like the AYR Deep End and the Summersalt Perfect Boyfriend Shirt. You can always go a size or two up with regular styles as well. They make a great beach cover up too.


Oversized Shirt Outfit Ideas

Oversized Button Down with Leggings

This is one of my go-to outfits for days when I need something comfortable and easy but still want to look put together. For warmer months I’ll wear sandals and/or biker shorts. As you can probably tell I love the AYR Deep End shirt because it’s so versatile. It comes in multiple colors in striped and solid. Outfit details: AYR Deep End Button Down, Summersalt Leggings, Converse

Oversized Button Down with Straight Leg Pants

A classic and chic combo I love a crisp button down with white straight leg pants. Good with sneakers or dress it up a little with loafers or ankle booties. Outfit Details: AYR Button Down, Straight Leg Pants, Converse

Oversized Button Down with Denim Shorts

A great outfit for summer, an oversized button down with high waist denim shorts. My favorite style that I’ve shared over the years is the AGolde Dee. I like to keep it comfy with sandals and a straw hat for added sun protection. Outfit details: AYR Button Down, AGolde Dee Denim Shorts, Sam Edelman Gala Sandals, Brixton Joanna Straw Hat

Oversized Stripe Long Sleeve Breton with Jeans

I have a real thing for an oversized breton and I really love the simplicity of a thick cotton stripe with denim. I usually wear loafers but sneakers are great too or ankle boots for fall. This style from Saint James is unisex so it’s a more straight fit (a good maternity option- see styling here). Outfit details: Saint James Meridien Moderne, AG Isabelle (same style this wash is a few years old), Sam Edelman Loafers

Oversized Stripe Long Sleeve with Light Puffy Jacket

For chillier days I like to layer a breton with a light puffy like my Patagonia Nano Puff. It also looks great with the Barbour Beadnell Jacket. Outfit details: Saint James Meridien Moderne, AG Isabelle, Patagonia Nano Puff

Oversized Stripe Long Sleeve with Biker Shorts and Sneakers

This is one of my favorite combos for spring and summer. I usually do a half tuck with this breton as you can see below to give it a little shape but untucked works too. I actually made these biker shorts last summer from a pair of leggings because I wasn’t sure if I would still like this trend but I definitely still like them and might get another pair for summer because they’re great for hot days, especially for gardening, playing tennis, biking (lol). This pair from Summersalt looks comfy. Outfit details: Saint James Meridien Moderne, Biker Shorts, Converse

Oversized Tee With Blazer

I love a good, super soft, oversized tee. This one is a men’s tee I got years ago from a brand that no longer makes men’s tees, womp womp, but one brand I would definitely recommend is Threads4Thought. It’s where I get all of Craig’s t-shirts, he’s so picky and he loves them. For men’s I typically go with what my usual women’s size would be. I like how an oversized tee with a blazer is polished but still comfortable. Outfit details: OneThird Blazer, Similar Tee, Jeans, Loafers

Oversized Tee with Biker Shorts

A tee and biker shorts is a very simple casual outfit I wear often during the summer. There’s almost always a chance I’ll be cold at some point during the day regardless of the weather so I usually bring a light layer. Outfit details: Similar Tee, Similar Biker Shorts, Converse, Breton Long Sleeve

Oversized Tee with Chunky Cardigan

A great fall outfit idea especially for those days that start out cold but get warmer as the day goes on. I really like this cardigan because it’s chunky but slightly cropped so doesn’t feel too overwhelming. Another layered look I really like is an oversized button down with a cozy sweater. Outfit details: Doen Cardigan, Similar Tee, AG Isabelle Jeans, Sam Edelman Loafers

oversized blouse with blazer

I got this Doen Jane Blouse last year and I absolutely love it. It’s an oversized fit that’s super flowy and breezy (a great style for spring and summer). It’s the perfect beach cover up (the front buttons all the way up). I love it paired with a classic camel blazer and straight leg pants. Outfit details: Sezane Blazer, Jane Doen Blouse, Straight Leg Pants, Converse

oversized blouse with cardigan

This outfit may look familiar because it’s from my Week of Outfits. Another easy combo is the Jane Blouse with Denim and a Cardigan. Outfit Details: White & Warren Recycled Cotton Cardigan (JESS20 for 20% off), Doen Jane Blouse (this print is old), Etica Denim JeansSam Edelman Loafers

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5 Comments

  1. Karen wrote:

    Excellent! I love your fashion sense. Great tip about sizing up on the breton. Mine are all my regular small size and pretty snug fitting, I love this looser look.

    5.10.21 | Reply
    • Jess wrote:

      Thank you so much! Yeah bretons you really can be generous with the sizing especially if they’re the thicker cotton fabric because they will fit pretty snug.

      5.11.21 | Reply
  2. Amy wrote:

    Thank you for this post, I’m 5’4 and hourglass shaped so too long shirts are a struggle. I usually shop in the kids section to avoid them. These are great tips for grown up clothes!

    5.10.21 | Reply
    • Jess wrote:

      Thanks Amy.

      5.11.21 | Reply
  3. Rach wrote:

    You can’t go wrong with Breton stripe and I’ve always loved how you styled it. I’ve been going back and forth if I should try out the Saint James Meridien and I’ve always trusted your review, so looks like I’m gonna go for it!

    http://www.rdsobsessions.com

    5.11.21 | Reply