Guest Blog written by Maggie Winterfeldt

Growing up I learned from my mother that clothes can be a mutually beneficial present; when she gave my dad—who will never shop for himself—fabulous clothes at Christmas, we got a fabulously dressed dad for the entire New Year. It can, however, be a challenge to find properly fitting clothes that are affordable, fashionable, and—above all—that the men in your life will actually wear.

As a women’s fashion professional, I figured that shopping for men would be an easy transition. A few Christmases ago I realized how wrong I was while picking up last minute gifts in Bloomingdales. Entering the men’s department was like crossing into a foreign country. Somewhere in the narrow space between evening gowns and trousers I stopped understanding the dialect completely. Overwhelmed by the nuances of countless measurements, pleats, and cuffs, I quickly grabbed a lavender striped button down shirt and checked out. The next June, I stumbled across the present–still in its original packaging–in the back of a closet. The embarrassed recipient explained that he finds tab collars uncomfortable and only wears straight point or spread collars. In my haste, I had erroneously assumed that all collars were the same.

Determined never again to be caught in the slacks aisle with my pants down, I studied up on men’s apparel. With Christmas rapidly approaching I’ve abbreviated my acquired knowledge into a helpful directory of fundamental jargon, sizing, and gift ideas that will suit every man on your list.

Understand men’s sizing

Unlike the even number 0-20 scale used for women’s sizes, men’s sizes are generally defined simply in inches. Before heading to the store, it is important to peak at the tags on his current clothes and gather his measurements:

  • Pants require waist and inseam measurement.
  • Jackets require a chest measurement and a judgment call of short, regular, or long length.
  • Dress shirts require a sleeve and neck measurement. Tip: checkout the comprehensive Men’s Dress Shirt Buying Guide on
  • Belts are bought two inches bigger than the actual waist measurement, so if you are buying him 32” pants, accessorize with a 34” belt.

Finding the Right Style

When shopping for a man whose only new clothes this decade will be the ones he finds under the tree, think of the holidays as a time for new beginnings. Lay a foundation for long-term good dressing by purchasing basics such as denim, chinos, sweaters, and button down shirts. J.Crew and Banana Republic are great one-stop-shops for complete men’s dressing solutions.

  • The high quality, low priced cashmere sweaters from J.Crew can’t be beat. Half-zip and v-neck styles look sharp and flatter most frames:
  • A classic dark denim jean is casual cool and can be easily dressed up with a button down or sweater. Banana Republic offers a contemporary straight legged version, and their online store offers a large selection sizes:

Shopping for a stylish guy is the most fun, but also the most stressful; you have the added pressure of finding a gift worthy of someone with distinctive taste. For these people I skip the hyper trendy Ed Hardy and Christian Audigier and search out the unique.

  • You can’t go wrong with hip, high quality tees. J.Newbury’s products feature original hand drawn and hand screened artwork in classic American motifs against soft vintage and organic cotton.
  • If you know he wears dress shirts with French cuffs, consider giving cufflinks. Uncommon Goods sells unique sets created from authentic antique subway tokens from New York, San Francisco, Boston, Chicago and Las Angeles.

When in doubt…

Shopping for a manly man requires tact; you want to give clothes that will refine his look while still appealing to his masculine sensibilities. Practical items in tailored cuts will balance out both of these objectives.

  • The iron-free button downs at Banana Republic provide low maintenance style in contemporary color palettes.
  • The On The Road Travel Pack from Jack Black provides everything from Beard Lube to Industrial Strength Hand Healer within a convenient black travel case. The products’ no-fuss navy blue packaging and masculine, cologne scent will convert even the most rugged man into a grooming enthusiast.

Now you have the major purchases taken care of, but what about all the miscellaneous gifts required for stocking stuffing, Yankee swaps, and sending to your nephews in Maryland? For this, I have the perfect, one-size-fits-all solution. . .

Oberon Socks, is a line of luxury men’s dress socks with a kick that I run out of Charleston. Our designs feature classic argyle prints updated with novel embroidery that appeals to men of all ages.

You are now prepared to enter the men’s department. Happy holidays and best wishes for a fashionable new year!

About Maggie:

Maggie Winterfeldt grew up in a suburb of Boston, Massachusetts. She moved down South to study political science and art history at Vanderbilt University. After graduating in 2008, she followed her love of fashion to New York City for a job in marketing and PR at a women’s bridgewear label. She now resides in Charleston, South Carolina where she co-runs the men’s dress sock label, Oberon Socks and shares fashion musings on the her blog,

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