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This week’s Sports Illustrated Style Q&A will help you stay stylish throughout the holiday season, from holiday parties at the office to date nights and for all the chilly commutes in between.

By Shradha Mehta and Anisha Bhasin Mukherjee
December 04, 2015

This week’s Sports Illustrated Style Q&A will help you stay stylish throughout the holiday season, from holiday parties at the office to date nights and for all the chilly commutes in between. Find the right winter boots, seasonal coat and holiday gift, all without breaking your bank. You can find the previous edition of the Q&A here, and be sure to download Dress for the’s app, and check out the site’s men’s style section to keep up with the trends. 

Q: I need cold weather boots but I don't want to look ridiculous. What are some options? -Eddie

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A: Hi Eddie! Sigh, how does one avoid looking like a Sasquatch while wearing a pair of effective cold weather boots? Lucky for you we've searched high and low and have the best fashionable options to suit your style! 1) If you're rugged, one with nature and your winter wardrobe looks identical to the Brawny Man, go for the Blizzard Boot. Strictly functional, these Baffin Apex Extreme Winter Boots will keep the snow off and your feet dry. (After all, they’re made for arctic temps!) For a pair that’s less damage on your wallet try Hunter’s Original Lace Ups. 2) If you're the guy that suits up and pays attention to detail, may we suggest our Dapper Boot recommendations to tickle your fancy. Fellas, this one’s a bit pricey but will last a lifetime. Here's an affordable alternative for under $100. 3) Lastly, if you find yourself making fashion choices somewhere in between the Brawny Man and the Dapper Dude we’ve got a feeling you’re going to love these Dr. Martens available in black, blue and grey. With DFTD approved cold weather boot selections, feel as warm as the Night’s Watch while looking as suave as John Snow. Go ahead and wiggle those toes with joy!

Q: I just started dating a girl a few months ago and I guess it's expected for me to get her a Christmas gift. Since it's a new relationship, I don't want to spend more than $100. I know she loves handbags but I know nothing about them. What do I get? -Ryan

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A: Ryan, your lady is about to have the best Christmas ever and you are about to get some serious action underneath the mistletoe. There are plenty of amazing handbags under $100: here’s our roundup. This Rebecca Minkoff clutch is a best seller for a reason and will make all her friends so J. Can’t go wrong with a classic Longchamp Tote; roomy and fashionable. Score the designer must-have bag without the price tag with this DVF metallic evening bag. If she’s on the trendy side, this fringe trim shoulder bag is the perfect gift.  Move over Santa; Ryan is coming to town!

Q: What does one wear to a work holiday party? -Raj

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A: Hey Raj! It’s that time of year again–holiday work parties. Awkward mingling with your boss, someone from accounting having one too many spiked eggnogs and attempting to “dougie” and of course, fashion disasters. Thankfully, we can prevent the last one from happening with a few quick tips. Leave those ugly holiday sweaters at home and opt for a suave velvet blazer with a polka dot pocket square like this one from Weekend Casual. Skip the tie and throw on a classic white button-down shirt. Finish the look with navy slacks and some cap-toe oxfords. Make your boss swoon, dance battle the guy from accounting and flirt with your crush in IT. ‘Tis the season to be styling!

Q: I need your advice on winter coats. I need a nice one to wear to work, on dates, etc. but I'm on a budget. Can you help me find some? -Arthur 

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A: Hi Arthur! Sounds like you're on the hunt for the perfect go-to winter coat. As you're looking for something you can wear from work to dates we recommend selecting a classic silhouette like a double-breasted overcoat. Lucky for you the options are endless and can be found on a budget too! If you prefer keeping things preppy we suggest sticking to a traditional color palette. Check out this jacket for $99 available in all the right colors like black, grey, heather and charcoal. Looking for something that’s a bit more on trend? Consider embracing military details like this for $55 in a navy option. Lastly, for those extra cold days we suggest this coat for $140. Although a bit pricier than the rest, this jacket provides extra warmth due to its wool blend. We may not be able to help you find Mrs. Right when it comes to your dating scene but we’re sure we found you a winner amongst our winter jacket picks! 

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