If his shoes smell and his sweater is full of holes – it’s time to intervene. Obviously, our fashion sense is a bit better than your boyfriend’s, so lend him a hand this holiday season and get him what he really needs. And then of course, show off your man and his new threads to all of your friends. Check out our favorite gifts to go in his stocking this year:

Check out more of our top gifts including gifts for your man, gifts for your OCD friend, and gifts for your Martha Stewart mother. Shop our guides to the best v-neck sweaters and the best watches. Subscribe to our e-mail list for exclusive updates.

1. J. Crew knows boxers are a V-day hit for the gentleman. Choose from these “XO” or beer mug prints. The great thing is that no matter which you decide on, all boxers are 2 for $28.

2. A great jean is sometimes just what the cherub ordered and the iconic Levi’s brand has you covered. Try the Slim Straight 514 in the solid, dark 3D Coated rinse; he can wear them from day to night without missing a beat. Order a second pair and you get free shipping.

3. What goes great with a pair of jeans? A crisp button down. The sharp BDG Solid Button Down Collar Shirt ($48) gives a nice, clean look regardless if it’s being worn casually or with a tie underneath a suit jacket.

4. Old Navy has a fantastic selection of basic layering or wear-alone tees available in a plethora of colors for only $3.99. Classic V-necks are going for 2 or more at $7.50 each.

5. A hooded cardigan like this Projek Raw Knit Jacket with Removable Hood ($130) is modern and stylish, a great piece to add to his wardrobe. He can wear it throughout the remainder of winter and into spring.

Don’t miss our other guides to the best Valentine’s Day gifts, perfect anytime gifts, and these stylish finds for guys.

Brooks Brothers’ exclusive, limited edition Mad Men suit went on sale today.  The slim, 1960s style was created in conjunction with Janie Bryant, Mad Men’s costume designer, and the gray sharkskin look is perfect for your guy.  Even if he’s not usually a sport about wearing a suit, we’re pretty sure he’ll have no argument if you tell him he looks like Don Draper.

We’re just getting into Halloween fever, and this is the ultimate reminder that something can both pass as a costume and be an incredible garment to wear every single other day of the year.  But do hurry – the suit is only available until the show’s season finale, on November 8th

Don’t want your man stealing the spotlight?  Be sure to don a proper cocktail dress, hosiery, and a sexy bra in order to sidle up in style next to anyone sporting the Mad Men suit.

What:
Roland Lodoli’s Push-Up Underpants

Why: We females already know the appeal of using a little architecture to keep ourselves looking our absolute best. Now a Croatian designer is giving men the same opportunity. Lodoli’s Wonderbra-inspired creation contains a small pocket inside that is designed to lift a man’s “goods” in order to make them look more impressive.

My first instinct is that this is super weird. However, since a good push-up bra can provide a healthy dose of confidence for us, shouldn’t men be entitled to the same thing? Would you be okay with your man wearing these? I’m mostly just upset that Lodoli didn’t give his product the most obvious, awesome name ever: WonderPants.

Right now these babies are not sold online, so unless your honey has
recently traveled to Croatia there isn’t much chance of this coming up (pun intended)
in real life, at least for now.

When you need a break from pondering these important questions, check out our Best Bras guide for SheFinds’ favorite ways to give ourselves a lift. Or check out Bare Essentials Top 10 Bras for Spring for the latest styles.

What: Titanium & Black Cable Dog Tag Chain, $149

Why: Jewelry for men is one of those taboo topics rarely uttered in mixed company. I mean, even the phrase conjures images of Tony Soprano and his entourage. So I’m a strong believer in less is so much more—both in the amount of jewelry worn and the design.

If you’re looking for that special Valentine’s Day gift, chains (men don’t wear “necklaces”) have become popular again and we love the Titanium & Black Cable Dog Tag Chain from Zales. The simple, modern design is sophisticated with a bit of edge. Other types of jewelry we think are acceptable include brushed metal watches, cuff links with personality, and tie bars (although these may be a bit too trendy for some guys).

There are a few items we do not encourage you to pursue. Unless it’s a wedding band, rings are too difficult for men to pull off because most are so gaudy. Dare I even have to say that the chance to wear an earring has long passed for him. At lastly, the bracelet – no matter how thin and understated it may seem  – absolutely not.

Receive free shipping on this chain as well as any order over $149 from Zales.com.

Get Yours: Zales.com