TSM Travel Diaries: Relaxing under the Tuscan sun in Boyfriend Jeans Pt. 2

I couldn’t blend in as a local in Europe even if I tried. A rustic doorway, snap, I have to take a picture. Food? click, click click, that stuff is definitely going on instagram…Oooh, a pebble, let me rearrange it so it looks extra special snap snap snap. Laugh as you may, I’m actually not as bad as some of my friends :P It’s definitely hard not to take so many photos in Europe when every turn of the corner looks like it belongs on a postcard or in a nostalgic foreign film. When I spend time filtering through these images, the embarrassment is long forgotten; I have these unique moments ingrained in my memory and captured on film to share with everyone for years to come.

Siena Tuscany coloured housesI was giddy with excitement over these beautiful and bright coloured residential homes in Siena. Something as mundane as locals hanging their washing out to dry just adds to authentic Tuscan look don’t you think?Siena Duomo


san gimignano tuscany

Sangiminano old town dusk

A dreamy Sangimiano by dusk …

san gimignano hills of tuscany


Antinori WineryWhile in Tuscany, we enrolled a cooking class for a day at  with Katia and Fulvio in San Gimignano which was such an enjoyable experiencing making pasta from scratch and then filling our bellies with the fruits of our labour. 
Tuscan cooking School picci pasta
how to wear boyfriend jeans

Psst … these are officially my favourite pair of casual jeans for travelling. Remember how I was on search of the perfect boyfriend jeans here? These Zara Boyfriend Jeans fit my budget (£40 from memory) and are the most comfy pair I own (perfect for over indulging in Tiramisu and wine). I’m yet to dress them up with heels but for now, am content with a more casual look. Hope you enjoyed both Pt 1 and Pt 2 of my Tuscany Travel diary xo

TSM Answered: How to wear Boyfriend Jeans

Kallopi Asked

Hi Tien, I’m 32 years old and I’m from Greece and a teacher. I really like your work and style and was wondering if you could give some advice on how to wear boyfriend jeans. Looking forward to hearing from you!

T-Styled Me Answered

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 are 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 effortly 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 :

1. 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:

A. 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 netural shades with the lighter coloured denim

B. DISTRESSED BOYFRIEND JEAN + SLOUCHY TEXTURED KNIT OR  A SHIRT

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

OPTIONAL ACCESSORIES : Hat, Statement Jewellery and Winter Coat

2. BOYFRIEND JEANS FOR A DRESSIER CASUAL LUXE LOOK

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

A. DARKER BOYFRIEND JEANS + NEUTRAL TEE + FITTED JACKET

SHOES: Heels (a must!) or heeled boots

OPTIONAL ACCESSORIES: Trilby, Clutch and Sunglasses for Summer

 B. BOYFRIEND JEAN + PRETTY / BRIGHT / GRAPHIC TOP

SHOES: Heels with detailing / colour / texture

OPTIONAL ACCESSORIES: Minimal Jewellery. Let the 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 the jeans.
  • Contrary to popular belief, boyfriend jeans don’t make you look larger than you are. You really only need to go 1-2 (at most) sizes up on your usual size.
  • If your conscious of your bottom half, opt for a darker hue and emphasise 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 boyfriend jeans I’ll be sure to do a styling post on them too!