Hi Kallopi! Thanks for your message and can I just say, totally off topic, that I absolutely love holidaying in Greece, especially the Greek Islands and Kefalonia remains one of my top three destination highlights of my entire European experiences over the past few years!

Boyfriend jeans. Your question could not have come at a better time because I’ve been personally shopping around for a pair recently and I’m ready to start experimenting with them in preparation for Spring.

I think that the great thing about Boyfriend jeans is that they are affordable and easily obtainable (consider your high street stores like Zara, H&M, local department stores but don’t forget your local thrift/vintage store, your bf’s or dare I say, your parents’ closet too!).

Boyfriend jeans aren’t going out of fashion any time soon and effort exude a cool, comfortable casual look that can be dressed up to suit your style and personality.

I’d say there are two main ways you can wear your boyfriend jeans:

Boyfriend Jeans For A Casual Tomboy Look

This style is suitable for weekend wear, casual dates with friends and in my mind, perfect for early morning trips to the farmer’s market or short flights when travelling. It’s all about effortless comfort. Here are some suggestions of what I would try for this look:

Distressed Boyfriend Jean + Tee (Graphic Or Plain) + Blazer

SHOES: Oxfords, ballet flats, flat boots

OPTIONAL ACCESORIES: Long necklace, sunglasses and an oversized bag and scarf

T-Styled me Tips: (1) For a more feminine look, roll your boyfriend jeans just above your ankles but be cautious about entering the capri zone which can cut off your legs and (2) If you’re short, avoid dark flat shoes and opt for light and neutral shades with the lighter colored denim

Distressed Boyfriend Jean + Slouchy Textured Knit Or A Shirt

SHOES: Sneakers (flat or wedged), and casual heel boots or Wedges

OPTIONAL ACCESSORIES: Hat, Statement Jewelry and Winter Coat

Boyfriend Jeans For A Dressier Casual Luxe Look

This style is perfect for going out while keeping it low-key. It’s an effort chic look that can easily be put together. It’s all about the shoes and accessories dressing up the jeans.

Darker Boyfriend Jeans + Neutral Tee + Fitted Jacket

SHOES: Heels (a must!) or heeled boots

OPTIONAL ACCESSORIES: Trilby, Clutch and Sunglasses for Summer

Boyfriend Jean + Pretty / Bright / Graphic Top

SHOES: Heels with detailing / color / texture

OPTIONAL ACCESSORIES: Minimal Jewelry. Let the shoes do the talking!

All photos sourced from

T-Styled Me Tips On Finding The Right Pair Of Boyfriend Jeans

Always try the jeans on and bring a pair of heels to get a feel for how you’d dress up in the jeans.

Contrary to popular belief, boyfriend jeans don’t make you look larger than you are. You only need to go 1-2 (at most) sizes up on your usual size.

If you’re conscious of your bottom half, opt for a darker hue and emphasize the detailing of your belt or the shoes/shirt.

I hope this was helpful Kallopi. Good luck and when I find my perfect pair of boyfriends jeans, I’ll be sure to do a styling post on them too!