How To Wear It: The Boyfriend Look

By fashion contributor Ashley. Read more about my talented group of contributors right here.

I’ve noticed a lot of clothing labeled “boyfriend” and decided it might be fun to do a little round up and share tips on how to wear the “boyfriend look”. Overall its a comfortable and relaxed style but with little bits and pieces that still sing to womanhood.


Look One: Perfect for an evening stroll or sipping cider.
1. My husband said this sweater looked more old man than a “boyfriend”…. but I say if it’s oversized then its the boyfriend.
2. An easy way to add a little bit of femininity back into this boyfriend look is by layering it with a peter pan collar.
3. I’m excited about wool felt hats this fall and decided they were a perfect match for this look because of their farm boy hat shape.
4. If you look at the bottom half of these boots they look just like a mens dress shoe!
5. The sexy boyfriend jean…. SUPER comfortable, yet stylish.
6. My husband has this mens Timex watch in black and its classy enough for both him and I!

Look Two: Great for picking apples and tromping through pumpkin patches
1. Oversized flannel button up. You can also find a fitted version if you want a more curvy look.
2. This plain v-neck tee comes from the mens section at H&M and is my new favorite. Great for layering and is loose but hangs nice.
3. Wearing a slouchy beanie with this look keeps things relaxed and helps draw attention to one of our best features, the face.
4. What man wouldn’t LOVE to have a motorcycle? These biker boots when styled correctly can be a perfect accent to the feminine boyfriend look.
5. To keep this look feminine wear some leggings to hug the shape of your legs and show off some curves.
6. A mans gold watch can take this look to the next step with its oversized face and bright finish. My friend once found a GREAT one at the drug store for less than $20.


I’m pretty sure I own everything with look #2. If you’re not comfortable style is not worth it!

Haha! I bought that Timex for my husband, and sometimes (when traveling) we share it. Love it. They also make a slightly smaller version (for the ladies), but I like the bigger one…

I’m glad I’m not the only one who steals their husbands watches (with permission of course). Good thing husbands are a lot easier to share with than sisters!

Comments are closed.