5 Classic, Stylish Gifts for Your Fashion-Challenged Boyfriend

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I may not be the most knowledgeable person when it comes to relationships, considering I haven’t been on a date in eons [ed. note: Sara just joined HowAboutWe — ask her out!], but as a blogger and employee at a fashion publication, I know my way around a store. In fact, I now have it down to a science. I’m in and then I’m out.

Keeping that in mind, I am confident that the products I am about to suggest to you will turn your fashion-challenged boyfriend — who I’m sure has a lovely personality! — into your boyfriend who has a lovely personality and great style. Allow me to introduce you to the handiest, dandiest, most useful gift guide you’ve seen yet.
1. A pair of Bonobos trousers:

This e-commerce site was created to find a solution for ill-fitting pants, and since I truly believe that a nice pair of pants makes the man, why not get him some bottoms to show off his bottom?

[; Grey Olive Herringbone Striped Pants shown at right]

2. Monogrammed cufflinks:

Nothing says “I care” more than something personalized.

[Cufflink Aficionado; Stainless Steel Engravable Block Cufflinks shown at left]

3. A statement — not silly — tie:
Please note the difference between the two. You want his tie to say something about his hobbies or his sense of humor without making people cringe. There are tons of great sites on Etsy that focus solely on ties. My recommendations are Tie Story, Scatterbrain Ties, and Knot Now.

[Etsy; Pink Poison tie by tiestory shown at right]

4. Classic sunglasses:

Yes, I am suggesting a pair of Ray-Ban Wayfarers. They look good on almost every person and add an instant air of bad-ass to any outfit.

[Ray-Ban; Original Wayfarer in Tortoise shown at left]

5. A garbage can:

To throw out his ugly sh*t. Oh, just kidding, that would be harsh—no, but seriously. (Maybe donate them to Sal Arm if you’d feel too guilty…)

[The Container Store; simplehuman 8 gal. Retro Step Can shown at right]

Sure, I could’ve recommended a pair of shoes that don’t look like they’re from Costco or a super-manly henley, but every man is different. He may love his Costco shoes! And there is nothing wrong with that! Rather, the suggestions above are merely items he may not realize he needs that will pull his look together a bit more.

But if you think he might be offended by the fact that you obviously think his fashion sense needs some work, maybe have a six-pack — or a twelve-pack? — of his favorite beer on hand.

[image via]

Sara Zucker is a blogger at, tweeter at @sbz, and Community Manager at a major fashion publication. She enjoys Lisa Frank stickers, drinking too much Prosecco at family functions, tripping on her own feet, and watching videos of hamsters eating vegetables.

You can also find her on HowAboutWe here.